[ CAS No. 5536-17-4 ] {[proInfo.proName]}

Name: 5536-17-4|(2R,3S,4S,5R)-2-(6-Amino-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol|98%
Brand: Ambeed
SKU: A153495
Price: 5.0 USD
Availability: InStock
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Quality Control of [ 5536-17-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 5536-17-4 ]

SDS Specification

Alternatived Products of [ 5536-17-4 ]

Product Details of [ 5536-17-4 ]

CAS No. :	5536-17-4	MDL No. :	MFCD00065471
Formula :	C₁₀H₁₃N₅O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OIRDTQYFTABQOQ-UHTZMRCNSA-N
M.W :	267.24	Pubchem ID :	21704
Synonyms :	Vira-A;NSC 404241;9-beta-Arabinofuranosyladenine;Arabinofuranosyladenine;NSC 247519;Arabinosyladenine;9-β-D-Arabinofuranosyladenine;Adenine Arabinoside;Ara-A

Calculated chemistry of [ 5536-17-4 ]

Physicochemical Properties

Num. heavy atoms :	19
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.5
Num. rotatable bonds :	2
Num. H-bond acceptors :	7.0
Num. H-bond donors :	4.0
Molar Refractivity :	62.67
TPSA :	139.54 Å²

Pharmacokinetics

GI absorption :	Low
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) :	-8.68 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.71
Log Po/w (XLOGP3) :	-1.05
Log Po/w (WLOGP) :	-2.3
Log Po/w (MLOGP) :	-2.72
Log Po/w (SILICOS-IT) :	-2.37
Consensus Log Po/w :	-1.55

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	1.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.05
Solubility :	23.6 mg/ml ; 0.0883 mol/l
Class :	Very soluble
Log S (Ali) :	-1.39
Solubility :	10.8 mg/ml ; 0.0406 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	0.41
Solubility :	685.0 mg/ml ; 2.56 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	3.86

Safety of [ 5536-17-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 5536-17-4 ]

* 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.

Upstream synthesis route of [ 5536-17-4 ]
Downstream synthetic route of [ 5536-17-4 ]

[ 5536-17-4 ] Synthesis Path-Upstream 1~36

1
[ 65174-95-0 ]
[ 5536-17-4 ]

Yield	Reaction Conditions	Operation in experiment
80%	With ammonia In methanol at 20℃; for 20 h;	third step,The above solid 10g (0.033mol)Soluble in 100 mL saturated ammonia methanol,Stir the reaction at room temperature for 20hThen the solvent is concentrated to dryness under reduced pressure.Add 100mL hot water, stir, and then activated carbon 0.2g,Warming reflux for 20 minutes,Hot filter activated carbon,The filtrate fell to room temperature and crystallized.The solid was suction filtered and dried to obtain arabidoside 7g. Yield 80percent.

Reference： [1] Patent: CN107556356, 2018, A, . Location in patent: Paragraph 0019; 0020
[2] Chemical and Pharmaceutical Bulletin, 1983, vol. 31, # 5, p. 1582 - 1592
[3] Journal of Pharmaceutical Sciences, 1985, vol. 74, # 8, p. 825 - 830

2
[ 3257-73-6 ]
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Reference： [1] Synthesis, 1981, # 5, p. 396 - 397
[2] Organic and Biomolecular Chemistry, 2005, vol. 3, # 3, p. 462 - 470

3
[ 3083-77-0 ]
[ 66224-66-6 ]
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Reference： [1] Agricultural and Biological Chemistry, 1985, vol. 49, # 7, p. 2167 - 2171
[2] Agricultural and Biological Chemistry, 1985, vol. 49, # 7, p. 2167 - 2171
[3] Agricultural and Biological Chemistry, 1985, vol. 49, # 4, p. 1053 - 1058
[4] Carbohydrate Research, 1981, vol. 97, p. 139 - 146
[5] Process Biochemistry, 2012, vol. 47, # 12, p. 2182 - 2188
[6] Russian Journal of Bioorganic Chemistry, 2004, vol. 30, # 6, p. 553 - 560
[7] Agricultural and Biological Chemistry, 1985, vol. 49, # 4, p. 1053 - 1058
[8] ChemCatChem, 2017, vol. 9, # 24, p. 4614 - 4620

4
[ 3083-77-0 ]
[ 58-61-7 ]
[ 5536-17-4 ]

Reference： [1] Russian Journal of Bioorganic Chemistry, 2016, vol. 42, # 4, p. 372 - 380[2] Bioorg. Khim., 2016, vol. 42, # 4, p. 411 - 420,10

5
[ 76054-92-7 ]
[ 122-51-0 ]
[ 5536-17-4 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 2304 - 2309

6
[ 108321-99-9 ]
[ 66224-66-6 ]
[ 5536-17-4 ]

Reference： [1] Tetrahedron Letters, 2008, vol. 49, # 16, p. 2642 - 2645

7
[ 3083-77-0 ]
[ 66224-66-6 ]
[ 66-22-8 ]
[ 5536-17-4 ]

Reference： [1] RSC Advances, 2015, vol. 5, # 30, p. 23569 - 23577

8
[ 64854-81-5 ]
[ 5536-17-4 ]

Reference： [1] Green Chemistry, 2014, vol. 16, # 3, p. 1077 - 1081

9
[ 69304-45-6 ]
[ 5536-17-4 ]

Reference： [1] Tetrahedron, 1984, vol. 40, # 1, p. 125 - 135
[2] Chemical and Pharmaceutical Bulletin, 1983, vol. 31, # 5, p. 1582 - 1592

10
[ 66224-66-6 ]
[ 5536-17-4 ]

Reference： [1] ChemPlusChem, 2013, vol. 78, # 2, p. 157 - 165

11
[ 201677-06-7 ]
[ 5536-17-4 ]
[ 3228-71-5 ]

Reference： [1] Tetrahedron, 1998, vol. 54, # 3-4, p. 573 - 592

12
[ 76994-88-2 ]
[ 5536-17-4 ]

Reference： [1] Journal of the Chemical Society, Chemical Communications, 1980, # 24, p. 1191 - 1193

13
[ 136834-18-9 ]
[ 5536-17-4 ]

Reference： [1] Patent: WO2005/14607, 2005, A2, . Location in patent: Page/Page column 89

14
[ 15830-52-1 ]
[ 5536-17-4 ]

Reference： [1] Journal of Molecular Catalysis B: Enzymatic, 2010, vol. 62, # 3-4, p. 225 - 229

15
[ 3083-77-0 ]
[ 73-24-5 ]
[ 5536-17-4 ]

Reference： [1] Russian Journal of Bioorganic Chemistry, 2009, vol. 35, # 6, p. 739 - 745

16
[ 58-61-7 ]
[ 5536-17-4 ]

Reference： [1] Patent: CN107556356, 2018, A,
[2] Patent: CN107556356, 2018, A,
[3] Patent: CN107556356, 2018, A,
[4] Patent: CN107556356, 2018, A,
[5] Patent: CN107556356, 2018, A,

17
[ 52522-49-3 ]
[ 5536-17-4 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 2304 - 2309
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 2304 - 2309
[3] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 2304 - 2309

18
[ 4060-34-8 ]
[ 5536-17-4 ]

19
[ 37776-25-3 ]
[ 5536-17-4 ]

20
[ 88121-23-7 ]
[ 5536-17-4 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1983, vol. 31, # 5, p. 1582 - 1592

21
[ 88121-20-4 ]
[ 5536-17-4 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1983, vol. 31, # 5, p. 1582 - 1592

22
[ 132887-08-2 ]
[ 5536-17-4 ]

Reference： [1] Patent: CN107556356, 2018, A,
[2] Patent: CN107556356, 2018, A,

23
[ 76994-86-0 ]
[ 5536-17-4 ]

Reference： [1] Journal of the Chemical Society, Chemical Communications, 1980, # 24, p. 1191 - 1193

24
[ 69275-14-5 ]
[ 5536-17-4 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 2304 - 2309

25
[ 76054-98-3 ]
[ 5536-17-4 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 2304 - 2309

26
[ 76054-93-8 ]
[ 5536-17-4 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 2304 - 2309

27
[ 51549-15-6 ]
[ 5536-17-4 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 563 - 573

28
[ 62374-24-7 ]
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Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 563 - 573

29
[ 65926-28-5 ]
[ 5536-17-4 ]

Reference： [1] Journal of Pharmaceutical Sciences, 1985, vol. 74, # 8, p. 825 - 830

30
[ 65286-65-9 ]
[ 5536-17-4 ]
[ 65926-28-5 ]

Reference： [1] Journal of Pharmaceutical Sciences, 1985, vol. 74, # 8, p. 825 - 830

31
[ 2391-46-0 ]
[ 5536-17-4 ]

Reference： [1] Tetrahedron Letters, 1987, vol. 28, # 15, p. 1633 - 1636

32
[ 81841-70-5 ]
[ 5536-17-4 ]

Reference： [1] Tetrahedron Letters, 1987, vol. 28, # 15, p. 1633 - 1636

33
[ 634-01-5 ]
[ 5536-17-4 ]
[ 58-61-7 ]
[ 524-69-6 ]

Reference： [1] Doklady Chemistry, 1987, vol. 296, # 10, p. 431 - 434[2] Dokl. Akad. Nauk SSSR Ser. Khim., 1987, vol. 296, # 4, p. 872 - 876

34
[ 958-09-8 ]
[ 5536-17-4 ]
[ 58-61-7 ]
[ 524-69-6 ]

Reference： [1] Doklady Chemistry, 1987, vol. 296, # 10, p. 431 - 434[2] Dokl. Akad. Nauk SSSR Ser. Khim., 1987, vol. 296, # 4, p. 872 - 876

35
[ 362-75-4 ]
[ 5536-17-4 ]
[ 958-09-8 ]
[ 58-61-7 ]
[ 524-69-6 ]

Reference： [1] Doklady Chemistry, 1987, vol. 296, # 10, p. 431 - 434[2] Dokl. Akad. Nauk SSSR Ser. Khim., 1987, vol. 296, # 4, p. 872 - 876

36
[ 5536-17-4 ]
[ 136834-20-3 ]

Reference： [1] Patent: US2006/160758, 2006, A1, . Location in patent: Page/Page column 17
[2] Patent: WO2003/99840, 2003, A1, . Location in patent: Page 221-222
[3] Patent: WO2008/157438, 2008, A1,

[ 5536-17-4 ] Synthesis Path-Downstream 1~13

1
[ 69304-45-6 ]
[ 5536-17-4 ]

Reference： [1]Tetrahedron,1984,vol. 40,p. 125 - 135
[2]Chemical and Pharmaceutical Bulletin,1983,vol. 31,p. 1582 - 1592

2
[ 3083-77-0 ]
[ 66224-66-6 ]
[ 5536-17-4 ]

Yield	Reaction Conditions	Operation in experiment
	With Clostridium perfringens uridine phosphorylase; Aeromonas hydrophila purine nucleosidephosphorylase co-immobilized on glyoxyl-agarose; In aq. phosphate buffer; at 28℃; under 1034.32 Torr; for 192h;pH 7.5;Flow reactor; Green chemistry; Enzymatic reaction;	A solution of arabinofuranosyluracil (4, 16 mM) and adenine (5, 8 mM) was prepared in 50 mMphosphate buer pH 7.5 (1 L). The column (15 mm 150 mm) packed with immobilized CpUP andAhPNP (10 g, 10 mL) was washed with 50 mM phosphate buer pH 7.5 at 1.0 mL min1 for 30 min.The substrate solution was flowed into the system at 83 L min1 (residence time: 120 min), at 28 Cand 20 psi for 8 days. The reaction outcome was monitored by HPLC by collecting a sample of theexiting flow stream every 8 h. The exiting solution was collected into a flask, which was then cooled at4 C to favor the product precipitation. The solid was filtered under vacuum, washed with cooledwater (50 mL) and dried under vacuum. Vidarabine (11) was isolated in 55% yield as a white solid(1.1 g). 1H-NMR was in agreement with literature data [17].

Reference： [1]Agricultural and Biological Chemistry,1985,vol. 49,p. 2167 - 2171
[2]Agricultural and Biological Chemistry,1985,vol. 49,p. 2167 - 2171
[3]Agricultural and Biological Chemistry,1985,vol. 49,p. 1053 - 1058
[4]Carbohydrate Research,1981,vol. 97,p. 139 - 146
[5]Process Biochemistry,2012,vol. 47,p. 2182 - 2188
[6]Russian Journal of Bioorganic Chemistry,2004,vol. 30,p. 553 - 560
[7]Agricultural and Biological Chemistry,1985,vol. 49,p. 1053 - 1058
[8]ChemCatChem,2017,vol. 9,p. 4614 - 4620
[9]Molecules,2020,vol. 25

3
[ 69304-37-6 ]
[ 5536-17-4 ]
[ 87792-02-7 ]

Yield	Reaction Conditions	Operation in experiment
81%	With pyridine; In N,N-dimethyl-formamide; at 20℃;	[in analogy to reference] 9-beta-D-Arabinofuranosyladenine (2.00 g, 7.5 mmol) was coevaporated three times with anhydrous pyridine. The residue was suspended in a 1:1 mixture of 16 cm3 anhydrous pyridine and N,N-dimethylformamide. Subsequently, 3.07 g 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane (3.11 cm3, 9.7 mmol) was added dropwise and stirred at room temperature for 24 h. The suspension turned into a colorless solution and all volatiles were removed by high vacuum distillation at 40 C. The crude product was dissolved in methylene chloride and consecutively extracted with a solution of 5% sodium bicarbonate and saturated sodium chloride. After the organic phase was dried and evaporated,column chromatography (silica gel, 0 to 8% methanolin methylene chloride) was applied providing 3.07 g (81%) of compound 1 as white foam. TLC (10% methanol in methylene chloride): Rf = 0.49; 1H NMR (300 MHz, DMSO-d6): delta = 1.02-1.05 (m, 24H, (CH3)2CHSi), 1.10-1.14 (m, 4H, (CH3)2CHSi), 3.77-3.82 (m, 1H, H-C(4?)), 3.92 (dd, J = 2.6,12.4 Hz, 1H, H(a)-C(5?)), 4.10 (dd, J = 4.4, 12.6 Hz, 1H, H(b)-C(5?)), 4.50 (dd, J = 7.3, 13.7 Hz, 1H, H-C(2?)), 4.57 (dd, J = 7.7, 15.6 Hz, 1H, H-C(3?)), 5.78 (d, J = 5.7 Hz, 1H, HO-C(2?)), 6.20 (d, J = 6.4 Hz, 1H, H-C(1?)), 7.27 (s, 2H,H-N(6)), 8.04 (s, 1H, H-C(2)), 8.11 (s, 1H, H-C(8)) ppm; 13C NMR (75 MHz, DMSO-d6): delta = 11.99-12.83 ((CH3)2CHSi),16.79-17.35 ((CH3)2CHSi), 61.51 (C(5?)), 74.89 (C(2?/3?)), 75.14 (C(2?/3?)), 79.59 (C(4?)), 81.83 (C(1?)), 118.52(C(5)), 139.61 (C(8)), 149.55 (C(4)), 152.38 (C(2)), 156.00 (C(6)) ppm; ESI-MS: m/z calculated for [C22H40N5O5Si2]+([M + H]+): 510.2528, found 510.2562.

Reference： [1]Nucleosides and Nucleotides,1999,vol. 18,p. 137 - 151
[2]Tetrahedron,2000,vol. 56,p. 3167 - 3172
[3]Journal of Medicinal Chemistry,2001,vol. 44,p. 2080 - 2093
[4]Helvetica Chimica Acta,1993,vol. 76,p. 158 - 167
[5]Tetrahedron,2007,vol. 63,p. 6901 - 6908
[6]Journal of Medicinal Chemistry,2015,vol. 58,p. 7349 - 7369
[7]Tetrahedron Letters,1983,vol. 24,p. 3183 - 3186
[8]Monatshefte fur Chemie,2019
[9]RSC Advances,2016,vol. 6,p. 36231 - 36237
[10]Journal of the American Chemical Society,2016,vol. 138,p. 9069 - 9072
[11]Chemistry Letters,1984,p. 805 - 808
[12]Canadian Journal of Chemistry,1983,vol. 61,p. 1911 - 1920
[13]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 159 - 165
[14]Chemistry - A European Journal,2015,vol. 21,p. 10400 - 10407

4
[ 5536-17-4 ]
[ 13276-53-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) triphenylphosphine, 2.) diethyl azodicarboxylate / 1.) DMF, 0 deg C, 10 min, 2.) DMF, a) 0 deg C, 15 min, b) RT, 2 h 2: 11 percent / sodium borohydride / ethanol / 20 h / Heating

Reference： [1]Vinayak; Hansske; Robins [Journal of Heterocyclic Chemistry, 1993, vol. 30, # 5, p. 1181 - 1189]

5
[ 52522-49-3 ]
[ 5536-17-4 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 2304 - 2309
[2]Journal of the Chemical Society. Perkin transactions I,1980,p. 2304 - 2309
[3]Journal of the Chemical Society. Perkin transactions I,1980,p. 2304 - 2309

6
[ 5536-17-4 ]
[ 136834-20-3 ]

Yield	Reaction Conditions	Operation in experiment
		2'-Fluorodeoxyadenosine Amidites 2'-fluoro oligonucleotides were synthesized as described previously [Kawasaki, et. al., J. Med. Chem., 1993, 36, 831-841] and U.S. Pat. No. 5,670,633, herein incorporated by reference. Briefly, the protected nucleoside N6-benzoyl-2'-deoxy-2'-fluoroadenosine was synthesized utilizing commercially available 9-beta-D-arabinofuranosyladenine as starting material.
		2'-fluoro oligonucleotides were synthesized as described previously [Kawasaki, et. [AL.,] J. Med. Chem., 1993,36, 831-841] and United States patent 5,670, 633, herein incorporated by reference. The preparation of 2'-fluoropyrimidines containing [A] 5-methyl substitution are described in US Patent 5,861, 493. Briefly, the protected nucleoside N6-benzoyl-2'-deoxy-2'-fluoroadenosine was synthesized utilizing commercially available 9-beta-D-arabinofuranosyladenine as starting material and whereby the 2'-alpha-fluoro atom is introduced by a SN2-displacement of a 2'-beta-triflate group. Thus N6-benzoyl-9-beta-D-arabinofuranosyladenine was selectively protected in moderate yield as the 3', 5'-ditetrahydropyranyl [(THP)] intermediate. Deprotection of the THP and N6-benzoyl groups was accomplished using standard methodologies to obtain the 5'-dimethoxytrityl- (DMT) and 5'-DMT-3'- phosphoramidite intermediates.

Reference： [1]Patent: US2006/160758,2006,A1 .Location in patent: Page/Page column 17
[2]Patent: WO2003/99840,2003,A1 .Location in patent: Page 221-222
[3]Patent: WO2008/157438,2008,A1

7
[ 78-40-0 ]
[ 5536-17-4 ]
[ 29984-33-6 ]

Yield	Reaction Conditions	Operation in experiment
87.8%	With sodium hydroxide; trichlorophosphate In water at -15 - 0℃; for 2.5h; Large scale;	3 Synthesis of arabinosyladenosine monophosphate: 1. Prepare a 40% aqueous sodium hydroxide solution: Add 37.5kg of purified water to the 50L reactor.15.0 kg of sodium hydroxide was added in portions under stirring and stirred for dissolution and use. 2. Add 200-L reaction tank to β-D-adenosine10.0kg,Triethyl phosphate 100.0 kg, cooled to -15°C . 3. Add phosphorus oxychloride 10.2kg under stirring, and control the temperature no higher than 0°C.Dropping is completed within 3 to 5 hours;After the addition is complete, the reaction is stirred at -0°C for 150 minutes.TLC detected that the reaction reached the end and stopped the reaction.Phosphorus oxychloride is added dropwise with stirring10.2kg, control temperature is not higher than 0°C. 4. The reaction solution was slowly pumped into a 500 L reaction tank (containing 150 kg of purified water pre-frozen to 2°C).The control temperature is not higher than 15°C. 5, cooling to 0 °C, adding 40% NaOH aqueous solution, adjust the pH to 2.0, control the temperature is not higher than15°C. 6. Add 67kg of dichloromethane to extract 3 times. Combine the aqueous phase. Add 0.5kg of activated carbon to the aqueous phase and decolorize for 30min.Activated carbon was filtered out, the temperature was controlled below 15 °C, the mass fraction of 40% NaOH aqueous solution was slowly adjusted to pH 2.5; 7, cooling to 15 °C, standing crystal 12h. 8. Centrifugation, washing the filtered crystals with 10 kg of cold purified water (about 15° C.) to obtain adenosine monophosphate wet crude product. Refinement of adenosine monophosphate. 1. Prepare an aqueous sodium hydroxide solution with a mass fraction of 40%: Add 20ml of purified water to the reactor and stirAdd 5.0 kg of sodium hydroxide in portions and stir and dissolve for later use. 2. Prepare hydrochloric acid aqueous solution with 10% mass fraction: Add 20kg of purified water to the reactor with a mass fraction of36% concentrated hydrochloric acid 5kg, stir and mix until use. 3. Add 200L of purified water and the above-mentioned monophosphate adenosine wet crude product in a 200L reaction vessel, and mix the mass fraction under stirring.A 40% aqueous solution of sodium hydroxide adjusted the pH in the kettle to 7. 4. Add 500g of activated carbon, stir and decolorize for 30 minutes, filter by 0.45μm plate and frame filter and then 0.22μm plateThe frame filter was pressed into a 500 L crystallization tank, and a 10% by mass aqueous solution of hydrochloric acid was added dropwise. The temperature was adjusted to 15° C. and the pH was slowly adjusted to 2.5. 5, the above liquid cooling to 15 °C, standing crystal 12h. 6. Centrifugal, purified water 10kg (about 15 °C) and 30kg absolute ethanol, vacuum drying (55 °C, vacuum degree ≥-0.085 MPa, 10 hours), crushed and weighed to give an off-white solid, namely adenosine monophosphate.The total molar yield is 87.80% (based on β-D-adenosine)The selectivity is 90.2% and the purity is 99.9%.
	With trichlorophosphate In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; ethanol	3 EXAMPLE 3 EXAMPLE 3 To 100 ml. of triethyl phosphate was added 10.69 g. (0.04 mole) of anhydrous 9-(β-D-arabinofuranosyl)adenine in one portion with stirring. This mixture was cooled in an ice bath to 2° C. and 9.20 g. (0.06 mole) of phosphorus oxychloride was then added during a three-minute period, the temperature rising to about 4° C. The reaction mixture was stirred in the cold for 2 hours 30 minutes, after which the clear solution was poured into 80 g. of ice. This mixture was stirred in an ice bath to maintain a temperature below 10° C. while the pH was adjusted to 2 using 50% sodium hydroxide solution. The resulting turbid mixture was extracted twice using 100-ml. and 50-ml. portions of dichloromethane and the aqueous layer was again adjusted to pH 2 using additional caustic. After seeding, this solution was placed in the refrigerator overnight to give a dense white precipitate. This was stirred with a glass rod and again allowed to stand overnight in the cold. The white product was filtered and washed using 22 ml. of ice water, 35 ml. of cold 50% ethanol and 25 ml. of cold absolute ethanol. After drying in vacuo at 40° C., 9.60 g. (69.1% of theory) of the product, 9-(β-D-arabinofuranosyl)adenine, 5'-phosphate, was obtained which assayed as follows: The corrected yield of 9-(β-D-arabinofuranosyl)adenine, 5'-phosphate was therefore 62.1% of theory.

Reference： [1]Current Patent Assignee: HAINAN HULUWA PHARMACEUTICAL GROUP - CN107793458, 2018, A Location in patent: Page/Page column 5; 6; 7
[2]Current Patent Assignee: PFIZER INC - US4123609, 1978, A

8
[ 3083-77-0 ]
[ 58-61-7 ]
[ 5536-17-4 ]

Reference： [1]Russian Journal of Bioorganic Chemistry,2016,vol. 42,p. 372 - 380
Bioorg. Khim.,2016,vol. 42,p. 411 - 420,10

9
[ 73-40-5 ]
[ 5536-17-4 ]
[ 38819-10-2 ]