[ CAS No. 69655-05-6 ] {[proInfo.proName]}

Name: 69655-05-6|9-((2R,5S)-5-(Hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-ol|98%
Brand: Ambeed
SKU: A259943
Price: 5.0 USD
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Quality Control of [ 69655-05-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 69655-05-6 ]

Product Details of [ 69655-05-6 ]

CAS No. :	69655-05-6	MDL No. :	MFCD00077728
Formula :	C₁₀H₁₂N₄O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BXZVVICBKDXVGW-NKWVEPMBSA-N
M.W :	236.23	Pubchem ID :	135398739
Synonyms :	Didanosine;ddI;Videx EC;Videx;DIDEOXYINOSINE;69655-05-6;NSC 612049;2′,3′-Dideoxyinosine;ddl	Chemical Name :	9-((2R,5S)-5-(Hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-ol

Calculated chemistry of [ 69655-05-6 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.5
Num. rotatable bonds :	2
Num. H-bond acceptors :	6.0
Num. H-bond donors :	2.0
Molar Refractivity :	57.97
TPSA :	93.29 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-8.62 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.31
Log Po/w (XLOGP3) :	-1.24
Log Po/w (WLOGP) :	-0.12
Log Po/w (MLOGP) :	-0.75
Log Po/w (SILICOS-IT) :	-0.34
Consensus Log Po/w :	-0.23

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.78
Solubility :	38.9 mg/ml ; 0.165 mol/l
Class :	Very soluble
Log S (Ali) :	-0.22
Solubility :	141.0 mg/ml ; 0.598 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.99
Solubility :	24.1 mg/ml ; 0.102 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.28

Safety of [ 69655-05-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 69655-05-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 69655-05-6 ]

[ 69655-05-6 ] Synthesis Path-Downstream 1~88

1
[ 108-30-5 ]
[ 69655-05-6 ]
[ 142894-17-5 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 1338 - 1340

2
[ 42867-68-5 ]
[ 69655-05-6 ]

Reference： [1]Nucleosides, nucleotides and nucleic acids,2007,vol. 26,p. 985 - 988
[2]Journal of Organic Chemistry,1989,vol. 54,p. 2217 - 2225

3
[ 69655-05-6 ]
[ 131933-66-9 ]
[ 131933-73-8 ]

Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 1408 - 1414

4
[ 69655-05-6 ]
[ 254887-64-4 ]
C₁₃H₁₇N₄O₆PS [ No CAS ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,1993,vol. 74,p. 469 - 470

5
[ 69655-05-6 ]
[ 108-24-7 ]
[ 130676-58-3 ]

Reference： [1]Nucleosides and Nucleotides,1996,vol. 15,p. 1077 - 1095
[2]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 1338 - 1340

6
[ 69655-05-6 ]
[ 623-66-5 ]
[ 142894-15-3 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 1338 - 1340

7
[ 69655-05-6 ]
[ 638-08-4 ]
[ 142894-16-4 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 1338 - 1340

8
[ 4097-22-7 ]
[ 69655-05-6 ]
[ 4097-22-7 ]

Reference： [1]Tetrahedron Letters,1988,vol. 29,p. 1239 - 1242
[2]Tetrahedron Letters,1988,vol. 29,p. 1239 - 1242

9
[ 69655-05-6 ]
[ 93-97-0 ]
[ 117312-02-4 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 1338 - 1340

10
[ 389128-06-7 ]
[ 69655-05-6 ]

Reference： [1]Synthetic Communications,1992,vol. 22,p. 1481 - 1486

11
[ 141684-85-7 ]
[ 69655-05-6 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 3887 - 3894

12
[ 68-94-0 ]
[ 5983-09-5 ]
[ 69655-05-6 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1994,vol. 59,p. 2303 - 2330

13
[ 4097-22-7 ]
[ 69655-05-6 ]

Yield	Reaction Conditions	Operation in experiment
	immobilized rec human adenosine deaminase enzyme; In water; at 20 - 40℃; for 1.5 - 120h;pH 6.5 - 7.5;	100.0 g ddA is added to 1900 ml of water at 30 C. (mother liquor from previous runs can also be used). After the ddA has been added (complete dissolution is not necessary), 4000 U of immobilized rec human adenosine deaminase is added. The reaction is maintained at 30 C. while stirring. The reaction is complete (approximately 5-8 hours) when the level of residual ddA is less than or equal to 1% of the original amount of ddA added. The enzyme solids are removed by filtration (20-30 mum media) and the enzyme cake is washed with 100 ml water. The used enzyme is held as a wet cake at 0-5 C. (for up to 72 hours) and can be recycled to another batch. The ddI solution is filtered through a CUNO filtration pad (0.4 to 1 micron), then through 0.2 micron filter media. A column (h/d ratio=6) is slurry packed with 380 U of immobilized rec human adenosine deaminase with water. The column is washed with 30 mM of NH4OH to pH 9.5 then with water to pH 6.5-7.5. While maintaining the temperature at 20 C., a 4% solution of ddA in water is passed through the column at a rate of 7.2 mil/min. for 120 hours. The effluent from the column is at pH 9.2-9.5 and contains >99% ddI with <1% ddA remaining. The resulting ddI solution is filtered through a CUNO pad and a 0.21mu filter before final isolation. A column (h/d ratio=2.7) is slurry packed with 1000 U of immobilized rec human adenosine deaminase with water. 25.0 g of ddA is dissolved in 475 ml of water (or a mother liquor from previous batch, diluted with water to 475 ml) at 30 C. in a 3-neck round bottom flask equipped with a mechanical stirrer. The ddA solution is circulated at 30 C. through the enzyme column at -50 mL/min (circulation speed can be varied as necessary). [0093] The reaction is complete (approximately 3-9.5 hours) when the level of residual ddA is less than or equal to 1% of the original amount of ddA added by HPLC analysis. The column is then rinsed with 25 ml of water and can be held at 0-5 C. (for up to 72 hours) for reuse. The resulting ddI solution is filtered through a CUNO pad and a 0.2 mum filter before final isolation. The following Table describes the conversion of a 52-60 g/L solution of ddA in water to ddI using the microbial adenosine deaminase as described above versus an example using the recombinant human ADA immobilized enzyme following the general procedure in Example 4. As can be seen from the results of Table 2, the recombinant human immobilized enzyme is significantly more stable than microbial enzymes and allows for the completion of the reaction with less units of enzyme and in a short period of time.
	microbial adenosine deaminase enzyme; In water; at 37 - 40℃; for 16 - 24h;	Microbial ADA from recombinant E. coli was partially purified and isolated as an ammonium sulfate suspension. E. coli fermentation broth (42 U ADA/mL, 2 L) was centrifuged and the cell pellet was collected and washed with 1 L 100 mM phosphate buffer pH 7.5. The cells were again centrifuged and resuspended in 2 L of the above buffer plus 20% glycerol. The cells were passed once through a microfluidizer. Cell debris was removed by centrifugation and the resulting supernatant was concentrated by ultrafiltration through a 30,000 MWCO cassette. The enzyme was concentrated to a final titer of 390 U/ml. Ammonium sulfate was added to a 50% saturation, the resulting precipitate was collected by centrifugation and re-suspended in 100 ml deionized water. The final titer of the slurry was 740 U/ml; the protein content of the slurry was 75 mg/ml. [0098] The following Table describes the conversion of a 52-60 g/L solution of ddA in water to ddI using the microbial adenosine deaminase as described above versus an example using the recombinant human ADA immobilized enzyme following the general procedure in Example 4. As can be seen from the results of Table 2, the recombinant human immobilized enzyme is significantly more stable than microbial enzymes and allows for the completion of the reaction with less units of enzyme and in a short period of time.
	Enzymatic reaction;	After 368 g of a mixed solution of acetonitrile and water containing 19.4 wt% of 9-(2,5-O-diacetyl-3-bromo-3-deoxy-beta-D-xylofuranosyl)adenine (71.3 g, 172 mmol) was poured into a 500-ml eggplant-shaped flask, the solution was adjusted to the pH range of 8.5 to 10.5 by the addition of aqueous sodium hydroxide solution. Thereafter, 1.65 g of the fresh catalyst (B) (0.0046 equivalent on a basis of palladium atom) and 26.6 g of the wet catalyst (B) obtained just after collected without the drying process were added and hydrogen was blown into the reaction system to carry out a reduction reaction, with the reaction system being maintained under basic condition by use of aqueous sodium hydroxide solution. The reduction reaction was completed in 3.8 hours. After completion of the reduction, the reaction liquid was subjected to filtration to collect 33.4 g of the catalyst. It took 0.5 hours to take out the catalyst by filtration. Apart of the filtrate was subjected to saponification by the addition of aqueous sodium hydroxide solution. According to the quantitative analysis by HPLC, 2',3'-dideoxyadenosine was found to be obtained in a yield of 83%. The remaining filtrate was concentrated and subjected to saponification by the addition of aqueous sodium hydroxide solution. Through the steps of extraction and crystallization, 29.4 g of 2',3'-dideoxyadenosine was obtained in a yield of 66% as wet crystals (not dried). Furthermore, the obtained crystals were subjected to enzymatic deamination, whereby 2',3'-dideoxyinosine was obtained.

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 1189 - 1195
[2]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 1577 - 1582
[3]Pharmaceutical Research,1996,vol. 13,p. 1881 - 1886
[4]Patent: US2004/175804,2004,A1 .Location in patent: Page 7-8
[5]Patent: US2004/175804,2004,A1 .Location in patent: Page 8
[6]Patent: EP1849786,2007,A1 .Location in patent: Page/Page column 10

14
[ 30516-87-1 ]
[ 69655-05-6 ]
[ 171284-20-1 ]
(Rp)- and (Sp)-4-acetyloxybenzyl (3'-azido-3'-deoxythymidin-5-yl) (2',3'-dideoxyinosin-5'-yl) phosphate [ No CAS ]

Reference： [1]Nucleosides and Nucleotides,1995,vol. 14,p. 1545 - 1558

15
[ 30516-87-1 ]
[ 69655-05-6 ]
[ 171284-22-3 ]
(Rp)- and (Sp)-4-pivaloyloxybenzyl (3'-azido-3'-deoxythymidin-5-yl) (2',3'-dideoxyinosin-5'-yl) phosphate [ No CAS ]

Reference： [1]Nucleosides and Nucleotides,1995,vol. 14,p. 1545 - 1558

16
[ 30516-87-1 ]
[ 69655-05-6 ]
[ 171284-21-2 ]
(Rp)- and (Sp)-4-butanoyloxybenzyl (3'-azido-3'-deoxythymidin-5-yl) (2',3'-dideoxyinosin-5'-yl) phosphate [ No CAS ]

Reference： [1]Nucleosides and Nucleotides,1995,vol. 14,p. 1545 - 1558

17
[ 125790-82-1 ]
[ 13146-72-0 ]
[ 69655-05-6 ]

Reference： [1]Nucleosides and Nucleotides,1996,vol. 15,p. 31 - 45

18
[ 69655-05-6 ]
8-Bromo-9-((2R,5S)-5-hydroxymethyl-tetrahydro-furan-2-yl)-1,9-dihydro-purin-6-one [ No CAS ]

Reference： [1]Nucleosides and Nucleotides,1996,vol. 15,p. 1077 - 1095

19
[ 69655-05-6 ]
[ 18162-48-6 ]
[ 177779-56-5 ]

Reference： [1]Nucleosides and Nucleotides,1996,vol. 15,p. 1077 - 1095

20
[ 69655-05-6 ]
[ 1609-47-8 ]
2',3'-dideoxyinosine-5'-yl-O-ethyl carbonate [ No CAS ]

Reference： [1]Acta Chemica Scandinavica,1996,vol. 50,p. 609 - 622

21
[ 177779-55-4 ]
[ 69655-05-6 ]

Reference： [1]Nucleosides and Nucleotides,1996,vol. 15,p. 1077 - 1095

22
[ 69655-05-6 ]
1,2-dihexadecyl-sn-glycero-3-H-phosphonate triethylammonium salt [ No CAS ]
C₄₅H₈₃N₄O₇P [ No CAS ]

Reference： [1]Russian Journal of Bioorganic Chemistry,1996,vol. 22,p. 390 - 396

23
[ 69655-05-6 ]
[ 203568-78-9 ]
11-{4-[(2S,5R)-5-(6-Oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-2-ylmethoxycarbonyl]-butyl}-1,4,8,11-tetraaza-cyclotetradecane-1,4,8-tricarboxylic acid tri-tert-butyl ester [ No CAS ]

Reference： [1]Nucleosides and Nucleotides,1998,vol. 17,p. 957 - 968

24
[ 69655-05-6 ]
[ 208449-63-2 ]
11-{4-[(2S,5R)-5-(6-Oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-2-ylmethoxycarbonyl]-butyryl}-1,4,8,11-tetraaza-cyclotetradecane-1,4,8-tricarboxylic acid tri-tert-butyl ester [ No CAS ]

Reference： [1]Nucleosides and Nucleotides,1998,vol. 17,p. 957 - 968

25
[ 205189-72-6 ]
[ 69655-05-6 ]

Reference： [1]Nucleosides and Nucleotides,1998,vol. 17,p. 153 - 159

26
[ 69655-05-6 ]
[ 192752-93-5 ]
9-[(2R,5S)-5-(8-Methyl-4H-benzo[1,3,2]dioxaphosphinin-2-yloxymethyl)-tetrahydro-furan-2-yl]-1,9-dihydro-purin-6-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 1604 - 1614

27
[ 177779-56-5 ]
[ 69655-05-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry,1999,vol. 7,p. 2373 - 2379

Yield	Reaction Conditions	Operation in experiment
	In water; at 0 - 40℃; for 1h;pH 7.8 - 8.3;Purification / work up;	The ddI solution is distilled under vacuum at an internal batch temperature of 20-40 C. The distillation is stopped when the concentration of ddI reaches 10-12% w/v based on initial ddA. Typically the pH is 8.1-8.3 at this point. Additional water is added and distillation is then continued until the concentration again reaches 10-12%, and the pH of the ddI slurry is less than 8 (typically 7.8-7.9). The ddI suspension is cooled to 0-5 C. and held for at least 1 hour. The cold slurry is filtered and the cake is washed with 0-5 C. water. The mother liquor and aqueous wash can be retained for recycling in another batch. [0096] The cake is washed with 0-5 C. acetone. The solids are dried under vacuum at 45-50 C. to a constant weight. Yields of 82% for the first run and 96-99% for four subsequent runs (>96% overall) are expected with mother liquor recycling. The resulting ddI is >99% pure.

29
[ 69655-05-6 ]
[ 246023-08-5 ]
2',3'-dideoxyinosylyl-(5'->5')-N⁴-palmitoyl-2',3'-dideoxycytidine [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1999,vol. 34,p. 343 - 352

30
[ 108-55-4 ]
[ 69655-05-6 ]
Pentanedioic acid mono-[(2S,5R)-5-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-2-ylmethyl] ester [ No CAS ]

Reference： [1]Nucleosides, nucleotides and nucleic acids,2003,vol. 22,p. 829 - 831

31
[ 69655-05-6 ]
[ 152336-79-3 ]
Pentanedioic acid (2S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,5-dihydro-furan-2-ylmethyl ester (2S,5R)-5-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-2-ylmethyl ester [ No CAS ]

Reference： [1]Nucleosides, nucleotides and nucleic acids,2003,vol. 22,p. 829 - 831

32
[ 69655-05-6 ]
[ 128305-54-4 ]
Pentanedioic acid (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (2S,5R)-5-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-2-ylmethyl ester [ No CAS ]

Reference： [1]Nucleosides, nucleotides and nucleic acids,2003,vol. 22,p. 829 - 831

33
[ 69655-05-6 ]
Pentanedioic acid mono-[(2S,5R)-5-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-2-ylmethyl] ester [ No CAS ]
Pentanedioic acid bis-[(2S,5R)-5-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-2-ylmethyl] ester [ No CAS ]

Reference： [1]Nucleosides, nucleotides and nucleic acids,2003,vol. 22,p. 829 - 831

34
[ 69655-05-6 ]
[ 61447-32-3 ]
C₁₃H₁₉N₄O₄PS [ No CAS ]

Reference： [1]Chemistry Letters,2004,vol. 33,p. 116 - 117

35
[ 69655-05-6 ]
[ 676329-52-5 ]
C₁₆H₂₃N₄O₄PS [ No CAS ]

Reference： [1]Chemistry Letters,2004,vol. 33,p. 116 - 117

36
[ 69655-05-6 ]
[ 676329-49-0 ]
C₂₆H₄₅N₄O₄PS [ No CAS ]

Reference： [1]Chemistry Letters,2004,vol. 33,p. 116 - 117

37
[ 110143-10-7 ]
[ 69655-05-6 ]

Reference： [1]Pharmaceutical Research,1996,vol. 13,p. 1881 - 1886

38
[ 120503-34-6 ]
[ 69655-05-6 ]

Reference： [1]Pharmaceutical Research,1996,vol. 13,p. 1881 - 1886

39
[ 69655-05-6 ]
[ 530-62-1 ]
C₁₀H₁₁N₄O₃(CONCHCHNCH) [ No CAS ]

Reference： [1]Nucleosides, nucleotides and nucleic acids,2005,vol. 24,p. 523 - 525
[2]MedChemComm,2014,vol. 5,p. 622 - 631

40
C₅₀H₉₅N₂O₈P [ No CAS ]
[ 69655-05-6 ]
C₅₄H₉₂N₅O₁₁P [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2237 - 2240

41
[ 90393-21-8 ]
[ 69655-05-6 ]
C₅₀H₈₄N₄O₁₀ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2237 - 2240

42
5'-O-benzyl-2',3'-dideoxyinosine [ No CAS ]
[ 69655-05-6 ]

Reference： [1]Nucleosides, nucleotides and nucleic acids,2007,vol. 26,p. 985 - 988

43
[ 69655-05-6 ]
C₁₀H₁₁N₄O₃(COSCH₂CH₂NHCOOC₄H₉) [ No CAS ]

Reference： [1]Nucleosides, nucleotides and nucleic acids,2005,vol. 24,p. 523 - 525

44
[ 69655-05-6 ]
C₁₀H₁₁N₄O₃(COSCH₂CH₂NH₂) [ No CAS ]

Reference： [1]Nucleosides, nucleotides and nucleic acids,2005,vol. 24,p. 523 - 525

45
[ 69655-05-6 ]
C₁₀H₁₁N₄O₃(COSCH₂CH₂NHCO)C₁₀H₁₂N₅O₄ [ No CAS ]

Reference： [1]Nucleosides, nucleotides and nucleic acids,2005,vol. 24,p. 523 - 525

46
[ 69655-05-6 ]
C₁₀H₁₁N₄O₃(COSCH₂CH₂NHCO)C₁₀H₁₂N₅O₄ [ No CAS ]

Reference： [1]Nucleosides, nucleotides and nucleic acids,2005,vol. 24,p. 523 - 525

47
[ 69655-05-6 ]
C₁₀H₁₁N₄O₃(COSCH₂CH₂NHCO)C₁₀H₁₁N₂O₄ [ No CAS ]

Reference： [1]Nucleosides, nucleotides and nucleic acids,2005,vol. 24,p. 523 - 525

48
[ 69655-05-6 ]
Pentanedioic acid bis-[(2S,5R)-5-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-2-ylmethyl] ester [ No CAS ]

Reference： [1]Nucleosides, nucleotides and nucleic acids,2003,vol. 22,p. 829 - 831

49
1-(2-deoxy-α,β-D-erythro-pentofuranosyl)imidazo[4,5-d]pyridazine-4(5H)-one [ No CAS ]
[ 69655-05-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry,1999,vol. 7,p. 2373 - 2379
[2]Bioorganic and Medicinal Chemistry,1999,vol. 7,p. 2373 - 2379

50
[ 260562-59-2 ]
[ 69655-05-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry,1999,vol. 7,p. 2373 - 2379
[2]Bioorganic and Medicinal Chemistry,1999,vol. 7,p. 2373 - 2379

51
imidazole-1-carbothioic acid <i>O</i>-[2-(<i>tert</i>-butyl-dimethyl-silanyloxymethyl)-5-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl] ester [ No CAS ]
[ 69655-05-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry,1999,vol. 7,p. 2373 - 2379

52
[ 260562-60-5 ]
[ 69655-05-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry,1999,vol. 7,p. 2373 - 2379

53
[ 58-63-9 ]
[ 69655-05-6 ]

Reference： [1]Nucleosides and Nucleotides,1998,vol. 17,p. 153 - 159
[2]Synthetic Communications,1992,vol. 22,p. 1481 - 1486
[3]Journal of Organic Chemistry,1989,vol. 54,p. 2217 - 2225
[4]Journal of Organic Chemistry,1989,vol. 54,p. 2217 - 2225

54
[ 205189-74-8 ]
[ 69655-05-6 ]

Reference： [1]Nucleosides and Nucleotides,1998,vol. 17,p. 153 - 159

55
Methanesulfonic acid (2R,3R,4R,5R)-5-formyloxymethyl-4-methanesulfonyloxy-2-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester [ No CAS ]
[ 69655-05-6 ]

Reference： [1]Nucleosides and Nucleotides,1998,vol. 17,p. 153 - 159

56
[ 69655-05-6 ]
Phosphoric acid (R)-2,3-bis-hexadecyloxy-propyl ester (2S,5R)-5-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-2-ylmethyl ester [ No CAS ]

Reference： [1]Russian Journal of Bioorganic Chemistry,1996,vol. 22,p. 390 - 396

57
[ 69655-05-6 ]
Thiophosphoric acid O-((R)-2,3-bis-hexadecyloxy-propyl) ester O'-[(2S,5R)-5-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-2-ylmethyl] ester [ No CAS ]

Reference： [1]Russian Journal of Bioorganic Chemistry,1996,vol. 22,p. 390 - 396

58
[ 890-38-0 ]
[ 69655-05-6 ]

Reference： [1]Nucleosides and Nucleotides,1996,vol. 15,p. 1077 - 1095

59
[ 69655-05-6 ]
Acetic acid (2S,5R)-5-(8-bromo-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-2-ylmethyl ester [ No CAS ]

Reference： [1]Nucleosides and Nucleotides,1996,vol. 15,p. 1077 - 1095

60
[ 93778-57-5 ]
[ 69655-05-6 ]

Reference： [1]Nucleosides and Nucleotides,1996,vol. 15,p. 1077 - 1095

61
[ 177779-54-3 ]
[ 69655-05-6 ]

Reference： [1]Nucleosides and Nucleotides,1996,vol. 15,p. 1077 - 1095

62
[ 32780-06-6 ]
[ 69655-05-6 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 3887 - 3894

63
(3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-phenylselanyl-tetrahydro-furan-2-ol [ No CAS ]
[ 69655-05-6 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 3887 - 3894

64
[ 149656-26-8 ]
[ 69655-05-6 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 3887 - 3894

65
[ 102717-29-3 ]
[ 69655-05-6 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 3887 - 3894

66
[ 125440-13-3 ]
[ 69655-05-6 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 3887 - 3894

67
[ 115728-44-4 ]
[ 69655-05-6 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 3887 - 3894

68
[ 141684-81-3 ]
[ 69655-05-6 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 3887 - 3894

69
[ 141706-88-9 ]
[ 69655-05-6 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 3887 - 3894

70
[ 142504-05-0 ]
[ 69655-05-6 ]

Reference： [1]Synthetic Communications,1992,vol. 22,p. 1481 - 1486

71
[ 119818-51-8 ]
[ 69655-05-6 ]

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 2217 - 2225

72
[ 119794-34-2 ]
[ 69655-05-6 ]

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 2217 - 2225
[2]Journal of Organic Chemistry,1989,vol. 54,p. 2217 - 2225

73
[ 119794-36-4 ]
[ 69655-05-6 ]

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 2217 - 2225

74
[ 119794-35-3 ]
[ 69655-05-6 ]

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 2217 - 2225

75
[ 32780-07-7 ]
[ 69655-05-6 ]

Reference： [1]Tetrahedron Letters,1988,vol. 29,p. 1239 - 1242

76
[ 121087-11-4 ]
[ 69655-05-6 ]

Reference： [1]Tetrahedron Letters,1988,vol. 29,p. 1239 - 1242

77
[ 117174-27-3 ]
[ 69655-05-6 ]

Reference： [1]Tetrahedron Letters,1988,vol. 29,p. 1239 - 1242

78
[ 117174-29-5 ]
[ 69655-05-6 ]

Reference： [1]Tetrahedron Letters,1988,vol. 29,p. 1239 - 1242

79
[ 505-54-4 ]
[ 69655-05-6 ]
[ 879015-25-5 ]

Yield	Reaction Conditions	Operation in experiment
50.5%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 20℃;	A mixture of didanosine (300 mg), hexadecanedioic acid (1.26 g), dimethylaminopyridine (80 mg), N- (3- DIMETHYLAMINOPROPYL)-N -ETHYL-CARBODIIMIDE hydrochloride (300 mg) in THF (50 ml) was stirred overnight at ambient temperature. The mixture was evaporated and the title compound was isolated by flash chromatography (silica, methanol: CH2CL2=2 : 8) plus 2% NH3 solution (25%) as a white powder. Yield: 323 mg (50. 5%) NMR (DMSO-D6) : 1. 22-2. 50 (m), 4.14-4. 25 (m), 6. 24 (t), 8.07 (s), 8.24 (s). ) MS: 505 (M+H)
50.5%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 20℃;	A mixture of didanosine (300 mg) , hexadecanedioic acid (1.26 g) , dimethylaminopyridine (80 mg) , N- (3- dimethylaminopropyl) -N'-ethyl-carbodiimide hydrochloride (300 mg) in THF (50 ml) was stirred overnight at ambient temperature. The mixture was evaporated and the title compound was isolated by flash chromatography (silica, methanol:CH2Cl2=2:8) plus 2% NH3 solution (25%) as a white powder. Yield: 323 rag (50.5%)NMR (DMSO-d*) : 1.22 - 2.50 (m) , 4.14 - 4.25 (m) , 6.24 (t) , 8.07 (s) , 8.24 (s) .MS: 505 (M+H)

Reference： [1]Patent: WO2005/25552,2005,A2 .Location in patent: Page/Page column 35-36
[2]Patent: WO2006/30217,2006,A2 .Location in patent: Page/Page column 44-45

80
[ 100-21-0 ]
[ 69655-05-6 ]
[ 879015-30-2 ]

Yield	Reaction Conditions	Operation in experiment
12%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 0℃;	2, 3'dideoxyinosine (100 mg, 0.424 mmol), 1,4- benzenedicarboxylic acid (281 mg, 1.69 MMOL), DMAP (20 mg, 1.64 mmol) and THF (12 ml) was stirred on an ice bath. N- (-3-DIMETHYLAMINOPROPYL)-N - ethylcarbodiimidehydrochloride (106 mg, 0.553 mmol) was added. The mixture was shaken and stirred overnight. Aqueous ammonia (1 ml), MEOH (10 ml) and DCM (10 ml) was added. The mixture was shaken, silica added, concentrated and purified by chromatography on silica using 30-40% MEOH, 5% aqueous ammonia in DCM
12%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 0℃;	2, 3 'dideoxyinosine (100 mg, 0.424 mmol), 1,4- benzenedicarboxylic acid (281 mg, 1.69 mmol), DMAP (20 mg, 1.64 mmol) and THF (12 ml) was stirred on an ice bath. N- (-3-Dimethylaminopropyl) -N'- ethylcarbodiimidehydrochloride (106 mg, 0.553 mmol) was added. The mixture was shaken and stirred overnight. Aqueous ammonia (1 ml), MeOH (10 ml) and DCM (10 ml) was added. The mixture was shaken, silica added, concentrated and purified by chromatography on silica using 30-40% MeOH, 5% aqueous ammonia in DCM

Reference： [1]Patent: WO2005/25552,2005,A2 .Location in patent: Page/Page column 37
[2]Patent: WO2006/30217,2006,A2 .Location in patent: Page/Page column 46

81
[ 24424-99-5 ]
[ 69655-05-6 ]
[ 879015-29-9 ]

Yield	Reaction Conditions	Operation in experiment
46%	With 1,8-diazabicyclo[5.4.0]undec-7-ene;dmap; In DMF (N,N-dimethyl-formamide); at 0 - 20℃;	2 , 3 -DIDEOXYINOSINE (1 g, 4.24 mmol), 1, 8-Diaza-7- bicyclo [5.4. 0] undecene (1.29 g, 8.47 mmol), 4- DIMETHYLAMINOPYRIDINE (small catalytic amount) and DMF (10 ml) was stirred on an ice bath. Bocanhydride (1.4 g, 8.04 mmol) dissolved in DMF (10 ml) was added. The reaction mixture was stirred at room temperature over night. The reaction mixture was concentrated, 20 ml DCM added and washed with 3X20 ml NAHCO3. The organic phase was dried with sodium sulphate, filtered, concentrated and purified by chromatography on silica using 12. 5% MEOH 2% aqueous ammonia in DCM. Resulting in 611 mg white crystalline product. 46% Yield.
		2T , 3 '-dideoxyinosine (I g, 4.24 mmol) , l,8-Diaza-7- bicyclo[5.4.0]undecene (1.29 g, 8.47 mmol), 4- dimethylaminopyridine (small catalytic amount) and DMF (10 ml) was stirred on an ice bath. Bocanhydride (1.4 g, 8.04 mmol) dissolved in DMF (10 ml) was added. The reaction mixture was stirred at room temperature over night. The reaction mixture was concentrated, 20 ml DCM added and washed with 3x20 ml NaHCO3. The organic phase was dried with sodium sulphate, filtered, concentrated and purified by chromatography on silica using 12.5% MeOH 2% aqueous ammonia in DCM. Resulting in 611 mg white crystalline product.46% Yield.

Reference： [1]Patent: WO2005/25552,2005,A2 .Location in patent: Page/Page column 37
[2]Patent: WO2006/30217,2006,A2 .Location in patent: Page/Page column 46

82
[ 810694-79-2 ]
[ 69655-05-6 ]

Yield	Reaction Conditions	Operation in experiment
70%	With sodium hydroxide; hydrogen;palladium(II) hydroxide/carbon; In methanol; dichloromethane; N,N-dimethyl-formamide; at 20 - 100℃; under 760.051 Torr; for 24h;	Example 4 Synthesis of 2',3'-dideoxyinosine (DDI) To a N,N-dimethylformamide solution (1 mL) of N1,5'-O-dibenzyl-2',3'-dideoxyinosine (52 mg, 0.125 mmol), an aqueous solution of sodium hydroxide (0.3 mL) at a concentration of 1mol/L was added, and the mixture was stirred at room temperature for 2 hours. To the obtained solution, 20% palladium hydroxide - carbon (10 mg) was added, and the mixture was stirred at room temperature for 2 hours in an atmosphere of hydrogen (1 atm) and thereafter stirred at 80C for 16 hours and at 100C for 6 hours. The palladium catalyst was removed from the obtained reaction mixture by filtration, and the resultant filtrate was concentrated under reduced pressure. After purification by chromatography (using 10 g of silica gel and a mixed solvent of dichloromethane and methanol (4:1) as an eluding solution), 21 mg of the intended product was obtained in a yield of 70% as a white solid. 1H-NMR (DMSO-d6): delta 2.00-2.07 (m, 2H), delta 2.31-2.53 (m, 2H), delta 3.52 (m, 1H), delta 3.62 (m, 1H), delta 4.11 (m, 1H), delta 4.96 (m, 1H), delta 6.21 (d-d, 1H, J=6.8, 3.3 Hz); delta 8.05 (s, 1H), delta 8.33 (s, 1H). 13C-NMR (DMSO-d6): delta 25.77, 32.49, 62.96, 82.40, 84.80, 124.64, 138.54, 145.97, 147.94, 156.98. ESIMS m/z: 237 (M+H).

Reference： [1]Patent: EP1634882,2006,A1 .Location in patent: Page/Page column 11; 12

Yield	Reaction Conditions	Operation in experiment
		By following the procedure of part A and substituting 3'-deoxythymidine with the following: ... 2',3'-dideoxycytidine, 2',3'-dideoxyguanosine, 9-(2,3-dideoxy-beta-D-erythro-pentofuranosyl)2-aminopurine, 9-(2,3-dideoxy-beta-D-erythro-pentofuranosyl)2,6-diaminopurine, 9-(2,3-dideoxy-beta-D-erythro-pentofuranosyl)hypoxanthine, and 1-(2,3-dideoxy-beta-D-erythro-pentofuranosyl)5-trifluoromethyluracil;

84
sodium salt of 2',3'-didehydro-2',3'-dideoxyinosine [ No CAS ]
[ 69655-05-6 ]

Yield	Reaction Conditions	Operation in experiment
		2',3'-Dideoxy-2',31-didehydroinosine sodium salt (50 gm) is added to water (180 ml) and stirred for 20 minutes at 25 - 350C. Then the contents are hydrogenated under nitrogen atmosphere at 1.5 - 2.0 kg/cm2 hydrogen pressure at 15 - 2O0C using raney nickel catalyst for 7 - 8 hours. Filtered the reaction EPO <DP n="8"/>mass on celite bed and washed with water (25 ml). To the filtrate activated carbon (2 gm) is added and stirred for 20 minutes. Filtered the mass on celite bed and washed with water (25 ml). The filtrate is cooled to 5 - 150C, the pH is adjusted to 7.0 - 8.0 with dilute hydrochloric acid (13 ml water + 13 ml cone. HCI) at 5 - 150C and stirred for 2 hours 30 minutes. Filtered the mass, washed with water (40 ml). The resulting wet cake is added to water (120 ml), the temperature is raised to 65 - 750C and stirred for 20 minutes at the same temperature. The resulting solution is cooled to 25 - 350C and stirred for 1 hour 30 minutes. The reaction mass is then cooled to 10 - 150C and stirred for 1 hour 30 minutes. Filtered the solid, washed with the 40 ml of water and dried at 55 - 6O0C to give 30.5 gm of didanosine (HPLC Purity: 99.85%).
		Example 1; Preparation of DDI from 5'-acetoxy-D4l; 20 g of 5'-acetoxy-D4l was dissolved in 200 mL of acetonitrile. The solution was cooled to 5C. Aqueous NaOH was added dropwise to the reaction mixture while stirring and the pH of the solution was maintained above 8.5. The completion of the protecting group removal was followed by TLC. After deprotection, 70 g of Raney nickel was added and the intermediate was hydrogenated with hydrogen gas at room temperature and normal pressure. The completion of hydrogenation was determined by HPLC. The solution was condensed under reduced pressure, and then neutralized with acetic acid. The crystalline product was filtered and dried. About 14 g of a solid was obtained. The dried DDI was recrystallized from methanol to obtain high purity DDI.; Example 2; Preparation of DDI from 2',3'-Didehydro-5'-O-(2,5,5-trimethyl-1,3-dioxolan-4-on-2-yl)-2',3'-dideoxyinosine; 20 g of 2',3'-Didehydro-5'-O-(2,5,5-trimethyl-1,3-dioxolan-4-on-2-yl)-2',3'-dideoxyinosine was dissolved in 200 mL of acetonitrile. The solution was cooled to 5C. Aqueous NaOH was slowly added dropwise into the reaction mixture while stirring. The pH of the solution was maintained at above 8.5. The completion of deprotection was followed by TLC. After completion, 50 g of Raney Nickel was added and the intermediate was hydrogenated with hydrogen gas at room temperature and normal pressure. The completion of hydrogenation was followed by HPLC. The solution was condensed under reduced pressure, and then neutralized with acetic acid. The crystallized product was filtered and dried. About 9 g of solid was obtained. The dried DDI was recrystallized with methanol to obtain high purity DDI.
		Example 4; Preparation of DDI from purified X-D4l·nH2O; 100 g of Na-D4l·2H2O was dissolved in 1000 mL of methanol. The reaction vessel was flushed with nitrogen. 500 g of activated Raney nickel was added. The reaction mixture was placed under an atmosphere of hydrogen gas for 10 hours under normal pressure. The completion of the reaction was followed by HPLC. At the completion of the reaction, the solution was filtered and condensed under reduced pressure to a volume of 100 mL. The condensed solution was then cooled to room temperature, and acetic acid was added dropwise while stirring. The pH was adjusted to between 6.5 and 7 and a white solid crystallized out. The mixture was stirred for 1 hour at room temperature and filtered. The filter cake was washed with 100 mL of methanol and dried at a temperature of between 55C and 60C. About 60 g of DDI was obtained. If needed, a high purity product can be obtained by recrystallization from methanol.

Reference： [1]Patent: WO2007/4230,2007,A2 .Location in patent: Page/Page column 6-7
[2]Patent: EP1887013,2008,A1 .Location in patent: Page/Page column 3-4
[3]Patent: EP1887013,2008,A1 .Location in patent: Page/Page column 4

85
[ 1058191-47-1 ]
[ 69655-05-6 ]
[ 1058191-55-1 ]

Reference： [1]Nucleosides, nucleotides and nucleic acids,2007,vol. 26,p. 1103 - 1106

86
[ 1083178-08-8 ]
[ 69655-05-6 ]
5-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-2-yl-methyl (2S,5R)-(4,8,13,17,21)-pentamethyl-docosa-4,8,12,16,20-pentaenoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 84h;Product distribution / selectivity;	28 mg of N-hydroxybenzotriazole (0.18 mmol), 36 mg of didanosine (ddI, 0.15 mmol), 70 mg of O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluoroborate (0.18 mmol) and finally 62 mg of diisopropylethylamine (0.5 mmol) were added to a solution of 31 mg of (4,8,13,17,21-pentamethyl-docosa-4,8,12,16,20-pentaenoic acid (SqCOOH, 0.15 mmol) in anhydrous dimethylformamide (1.2 ml). The mixture was stirred for 84 hours at 20 C. in a nitrogen atmosphere, then concentrated under reduced pressure (0.05 Torr). The residue was taken up in 5 ml of a saturated aqueous solution of sodium bicarbonate, and extracted with ethyl acetate (3×10 ml). The organic phase was washed with an aqueous NaCl solution, dried over MgSO4 and concentrated under vacuum. The residue was chromatographed over silica gel (CH2Cl2/MeOH: 92/8) to produce 37 mg of 5'-squalenoyldidanosine (Yield 58%) in the form of a colorless amorphous solid.IR (cm-1) 3550-2700, 2921, 2856, 1734, 1691, 1590, 1548, 1449, 1380, 1261.1H NMR (200 MHz, CDCl3) delta: 13.0 (s broad, 1H), 8.18 (s, 1H), 8.08 (s, 1H), 6.38 (t, J=4.2 Hz, IH), 5.17-5.00 (m, 5H), 4.40-4.20 (m, 3H), 2.60-1.90 (m, 24H), 1.67 (s, 3H), 1.60 (s broad, 15H).13C NMR (50 MHz, CDCl3) delta: 173.27 (CO2), 159.20 (CO), 148.34 (C), 144.3 (CH) 138.60 (CH), 135.23 (C), 135.03 (C), 135.00 (C), 133.09 (C), 131.31 (C), 125.56 (CH), 125.38 (C), 125.54 (CH), 124.53 (CH), 124.40 (2 CH), 85.94 (CH), 79.60 (CH), 65.07 (CH2), 39.86 (CH2), 39.83 (CH2), 39.68 (CH2), 34.67 (CH2), 33.12 (CH2), 33.01 (CH2), 28.39 (CH2), 28.38 (CH2), 29.9 (CH2), 26.83 (CH2), 26.79 (CH2), 26.28 (CH2), 25.77 (CH3), 17.77 (CH3), 16.51 (2 CH3), 16.10 (CH3), 16.00 (CH3).The same compound could be obtained in a yield of 10% using EDCI as the coupling agent, while condensation between the squaloyl acid chloride and dI produced it in a yield of 15%.The particle size was determined using the protocol described in example 2. The hydrodynamic diameter mean was 152 nm, measured with a standard deviation of 34.4 nm and a polydispersity index of 0.1.
10%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride;Product distribution / selectivity;	28 mg of N-hydroxybenzotriazole (0.18 mmol), 36 mg of didanosine (ddI, 0.15 mmol), 70 mg of O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluoroborate (0.18 mmol) and finally 62 mg of diisopropylethylamine (0.5 mmol) were added to a solution of 31 mg of (4,8,13,17,21-pentamethyl-docosa-4,8,12,16,20-pentaenoic acid (SqCOOH, 0.15 mmol) in anhydrous dimethylformamide (1.2 ml). The mixture was stirred for 84 hours at 20 C. in a nitrogen atmosphere, then concentrated under reduced pressure (0.05 Torr). The residue was taken up in 5 ml of a saturated aqueous solution of sodium bicarbonate, and extracted with ethyl acetate (3×10 ml). The organic phase was washed with an aqueous NaCl solution, dried over MgSO4 and concentrated under vacuum. The residue was chromatographed over silica gel (CH2Cl2/MeOH: 92/8) to produce 37 mg of 5'-squalenoyldidanosine (Yield 58%) in the form of a colorless amorphous solid.IR (cm-1) 3550-2700, 2921, 2856, 1734, 1691, 1590, 1548, 1449, 1380, 1261.1H NMR (200 MHz, CDCl3) delta: 13.0 (s broad, 1H), 8.18 (s, 1H), 8.08 (s, 1H), 6.38 (t, J=4.2 Hz, IH), 5.17-5.00 (m, 5H), 4.40-4.20 (m, 3H), 2.60-1.90 (m, 24H), 1.67 (s, 3H), 1.60 (s broad, 15H).13C NMR (50 MHz, CDCl3) delta: 173.27 (CO2), 159.20 (CO), 148.34 (C), 144.3 (CH) 138.60 (CH), 135.23 (C), 135.03 (C), 135.00 (C), 133.09 (C), 131.31 (C), 125.56 (CH), 125.38 (C), 125.54 (CH), 124.53 (CH), 124.40 (2 CH), 85.94 (CH), 79.60 (CH), 65.07 (CH2), 39.86 (CH2), 39.83 (CH2), 39.68 (CH2), 34.67 (CH2), 33.12 (CH2), 33.01 (CH2), 28.39 (CH2), 28.38 (CH2), 29.9 (CH2), 26.83 (CH2), 26.79 (CH2), 26.28 (CH2), 25.77 (CH3), 17.77 (CH3), 16.51 (2 CH3), 16.10 (CH3), 16.00 (CH3).The same compound could be obtained in a yield of 10% using EDCI as the coupling agent, while condensation between the squaloyl acid chloride and dI produced it in a yield of 15%.The particle size was determined using the protocol described in example 2. The hydrodynamic diameter mean was 152 nm, measured with a standard deviation of 34.4 nm and a polydispersity index of 0.1.

Reference： [1]Patent: US2009/130214,2009,A1 .Location in patent: Page/Page column 5-6
[2]Patent: US2009/130214,2009,A1 .Location in patent: Page/Page column 5-6

87
squaloyl acid chloride [ No CAS ]
[ 69655-05-6 ]
5-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-2-yl-methyl (2S,5R)-(4,8,13,17,21)-pentamethyl-docosa-4,8,12,16,20-pentaenoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
15%	Product distribution / selectivity;	28 mg of N-hydroxybenzotriazole (0.18 mmol), 36 mg of didanosine (ddI, 0.15 mmol), 70 mg of O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluoroborate (0.18 mmol) and finally 62 mg of diisopropylethylamine (0.5 mmol) were added to a solution of 31 mg of (4,8,13,17,21-pentamethyl-docosa-4,8,12,16,20-pentaenoic acid (SqCOOH, 0.15 mmol) in anhydrous dimethylformamide (1.2 ml). The mixture was stirred for 84 hours at 20 C. in a nitrogen atmosphere, then concentrated under reduced pressure (0.05 Torr). The residue was taken up in 5 ml of a saturated aqueous solution of sodium bicarbonate, and extracted with ethyl acetate (3×10 ml). The organic phase was washed with an aqueous NaCl solution, dried over MgSO4 and concentrated under vacuum. The residue was chromatographed over silica gel (CH2Cl2/MeOH: 92/8) to produce 37 mg of 5'-squalenoyldidanosine (Yield 58%) in the form of a colorless amorphous solid.IR (cm-1) 3550-2700, 2921, 2856, 1734, 1691, 1590, 1548, 1449, 1380, 1261.1H NMR (200 MHz, CDCl3) delta: 13.0 (s broad, 1H), 8.18 (s, 1H), 8.08 (s, 1H), 6.38 (t, J=4.2 Hz, IH), 5.17-5.00 (m, 5H), 4.40-4.20 (m, 3H), 2.60-1.90 (m, 24H), 1.67 (s, 3H), 1.60 (s broad, 15H).13C NMR (50 MHz, CDCl3) delta: 173.27 (CO2), 159.20 (CO), 148.34 (C), 144.3 (CH) 138.60 (CH), 135.23 (C), 135.03 (C), 135.00 (C), 133.09 (C), 131.31 (C), 125.56 (CH), 125.38 (C), 125.54 (CH), 124.53 (CH), 124.40 (2 CH), 85.94 (CH), 79.60 (CH), 65.07 (CH2), 39.86 (CH2), 39.83 (CH2), 39.68 (CH2), 34.67 (CH2), 33.12 (CH2), 33.01 (CH2), 28.39 (CH2), 28.38 (CH2), 29.9 (CH2), 26.83 (CH2), 26.79 (CH2), 26.28 (CH2), 25.77 (CH3), 17.77 (CH3), 16.51 (2 CH3), 16.10 (CH3), 16.00 (CH3).The same compound could be obtained in a yield of 10% using EDCI as the coupling agent, while condensation between the squaloyl acid chloride and dI produced it in a yield of 15%.The particle size was determined using the protocol described in example 2. The hydrodynamic diameter mean was 152 nm, measured with a standard deviation of 34.4 nm and a polydispersity index of 0.1.

Reference： [1]Patent: US2009/130214,2009,A1 .Location in patent: Page/Page column 5-6

88
[ 1188435-93-9 ]
[ 69655-05-6 ]
[ 1188435-94-0 ]

Reference： [1]European Journal of Medicinal Chemistry,2009,vol. 44,p. 3874 - 3879

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P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 69655-05-6 ] {[proInfo.proName]}

Quality Control of [ 69655-05-6 ]

Related Doc. of [ 69655-05-6 ]

Product Details of [ 69655-05-6 ]

Calculated chemistry of [ 69655-05-6 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 69655-05-6 ]

Application In Synthesis of [ 69655-05-6 ]

[ 69655-05-6 ] Synthesis Path-Downstream 1~88

Precautionary Statements-General

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