[ CAS No. 892-48-8 ] {[proInfo.proName]}

Name: 892-48-8|5'-Chloro-5'-deoxyadenosine|97%
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SKU: A134694
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2D 3D

Structure of 892-48-8 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 892-48-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 892-48-8 ]

SDS Specification

Alternatived Products of [ 892-48-8 ]

Product Details of [ 892-48-8 ]

CAS No. :	892-48-8	MDL No. :	MFCD00049038
Formula :	C₁₀H₁₂ClN₅O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IYSNPOMTKFZDHZ-KQYNXXCUSA-N
M.W :	285.69	Pubchem ID :	5327118
Synonyms :

Calculated chemistry of [ 892-48-8 ]

Physicochemical Properties

Num. heavy atoms :	19
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.5
Num. rotatable bonds :	2
Num. H-bond acceptors :	6.0
Num. H-bond donors :	3.0
Molar Refractivity :	66.31
TPSA :	119.31 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) :	-8.09 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.98
Log Po/w (XLOGP3) :	-0.06
Log Po/w (WLOGP) :	-1.05
Log Po/w (MLOGP) :	-1.65
Log Po/w (SILICOS-IT) :	-1.25
Consensus Log Po/w :	-0.61

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.79
Solubility :	4.61 mg/ml ; 0.0161 mol/l
Class :	Very soluble
Log S (Ali) :	-1.99
Solubility :	2.89 mg/ml ; 0.0101 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.78
Solubility :	47.9 mg/ml ; 0.167 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	3.96

Safety of [ 892-48-8 ]

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 [ 892-48-8 ]

* 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 [ 892-48-8 ]
Downstream synthetic route of [ 892-48-8 ]

[ 892-48-8 ] Synthesis Path-Upstream 1~6

1
[ 58-61-7 ]
[ 892-48-8 ]

Yield	Reaction Conditions	Operation in experiment
89%	With thionyl chloride In N,N,N,N,N,N-hexamethylphosphoric triamide; water	EXAMPLE 2 Preparation of 5'-deoxy-5'-ethylthioadenosine 1 kg of adenosine is dissolved under a nitrogen atmosphere in 10 l of hexamethylphosphoramide, and 7.5 l of thionyl chloride are added under cooling. The mixture is left to react at ambient temperature for 20 hours. 10 l of water are added, and the mixture neutralised with 2 N NaOH. The 5'-deoxy-5'-chloroadenosine which thus forms is allowed to crystallise overnight at 3° C. It is filtered off. 0.950 kg of 5'-deoxy-5'-chloroadenosine are obtained (yield 89percent).
86%	Stage #1: With pyridine; thionyl chloride In acetonitrile at 0 - 5℃; Stage #2: With ammonium hydroxide In methanol; water; acetonitrile at 20℃; for 0.5 h;	Compound 308l-(3-((((2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2- yl)methyl)thio)propyl)-3-(4-(tert-butyI)phenyl)ureaStep 1. (2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5- (chloromethyl)tetrahydrofuran-3,4-diol To a solution of (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5- (hydroxymethyl)tetrahydrofuran-3,4-diol (1 g, 3.47 mmol) in pyridine (593 mg, 0.6 ml, 7.49 mmol) in acetonitrile (10ml) cooled in an ice bath was added SOCl₂ (2.22g, 1.36ml,18.65mmol). Stirring was continued at 0-5° C for 3-4 h, and warning to ambient temperature for overnight. The resulting suspension was concentrated in vacuo. To the reaction mixture was added methanol (20 ml), water (2ml), and NH₄OH (4 ml), followed by stirring for 0.5 h at room temperature. The reaction mixture was concentrated to dryness. The compound was dissolved in MeOH, silica gel (3g) was added and then solvent was removed. The residue was purified by SGC to elute with EA : MeOH (0percent-10percent) to obtain the title compound (0.915 g, yield 86percent) as yellowish solid. NMR (500 MHz, MeOD): δ 8.24 (s, 1H), 8.02 (s, 1H), 7.27-7.20 (m, 5H), 6.19 (d, J = 2.0 Hz, 1H), 5.48-5.46 (m, 1H), 5.08-5.06 (m, 1H), 4.43 (t, J = 4.0, Hz, 1H), 3.83- 3.81 (m, 2H).
86%	Stage #1: With pyridine; thionyl chloride In acetonitrile at 0 - 5℃; Stage #2: With ammonium hydroxide In methanol; water; acetonitrile at 20℃; for 0.5 h;	((3aS,4S,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2 dimethyltetrahydro furo[3,4- d][l,3]dioxol-4-yl)methanethiolStep 1. Preparation of (2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5- (chloromethyl) tetrahydrofuran-3,4-diolTo a solution of (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5- (hydroxymethyl)tetrahydrofuran-3,4-diol (1 g, 3.47 mmol) in pyridine (593 mg, 0.6 ml, 7.49 mmol) in acetonitrile (10ml) cooled in an ice bath was added SOCl₂ (2.22g, 1.36ml,18.65mmol). Stirring was continued at 0-5° C for 3-4 h, and warning to ambient temperature for overnight. The resulting suspension was concentrated in vacuo. To this reaction mixture was added methanol (20 ml), water (2ml), and NH₄OH (4 ml), followed by stirring for 0.5 h at room temperature. The reaction mixture was concentrated to dryness. The compound was dissolved in MeOH, silica gel (3g) was added and then solvent was removed. The residue was purified by SGC to elute with EA : MeOH (0percent-10 ) to obtain the target compound (0.915 g, yield 86percent) as yellowish solid. NMR (500 MHz, MeOD): δ 8.24 (s, IH), 8.02 (s, IH), 7.27-7.20 (m, 5H), 6.19 (d, / = 2.0 Hz, IH), 5.48-5.46 (m, IH), 5.08-5.06 (m, IH), 4.43 (t, J = 4.0, Hz, IH), 3.83- 3.81 (m, 2H), 3.01-2.99 (br s, 2H), 1.60 (s, 3H), 1.38 (s, 3H) ppm, LCMS (m/z): 395.8 [M+H]⁺.

60%

Stage #1: With pyridine; thionyl chloride In acetonitrile at 0 - 20℃;
Stage #2: With ammonium hydroxide In methanol; water at 20℃; for 0.5 h;

To a cold suspension (0°С) of adenosine (3.0 g, 11.2 mmol) in acetonitrile (35 ml) and pyridine (22.4 mmol, 1.8 ml), thionyl chloride (4.1 ml, 56.1 mmol) was slowly added and the mixture was stirred 4 h under 0°С.
The resulting solution was kept at ambient temperature overnight.
The precipitate was filtered and dissolved in H₂O/MeOH (5:50 ml) and 25percent aqueous ammonia (4.7 ml) was added to the mixture.
The reaction mixture was kept at ambient temperature for 30 min and evaporated in vacuum.
The residue was transferred to a glass filter, washed with cold water (2 * 20 ml) and dried in vacuum desiccator over P₂O₅.
Yield 1.92 g (60percent) as white crystals. R_f 0.15 (CH₂Cl₂-EtOH, 9:1 v/v).
¹H NMR (DMSO-d₆): δ = 3.84 (dd, 1H, J_5'b-4' = 6.3 Hz, J_5'ba = -11.6 Hz, H5'b), 3.94 (dd, 1H, J_5'a-4' = 5.1 Hz, J_5'ab = -11.6 Hz, H5'a), 4.10 (ddd, 1H, J_4'-5'b = 6.3 Hz, J_4'-5'a = 5.1 Hz, J_4'-3' = 4 Hz, H4'), 4.23 (ddd, 1H, J_3'-4' = 4 Hz, J_3'-OH = 5.1 Hz, J_3'-2' = 5 Hz, H3'), 4.75 (dd, 1H, J_2'-3' = 5 Hz, J_2'-1' = 5.6 Hz, H2'), 5.41 (d, 1H, J_OH-3' = 5.1 Hz, 3'OH), 5.56 (d, 1H, J_OH-2' = 6.03 Hz, 2'OH), 5.93 (d, 1H, J_1'-2' = 5.6 Hz, H1'), 7.26 (s, 2H, NH₂), 8.15 (s, 1H, H8), 8.33 (s, 1H, H2).

Reference： [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 18, p. 8066 - 8074,9
[2] Angewandte Chemie - International Edition, 2016, vol. 55, # 46, p. 14277 - 14280[3] Angew. Chem., 2016, vol. 128, # 46, p. 14489 - 14492,4
[4] Tetrahedron Letters, 2018, vol. 59, # 4, p. 415 - 417
[5] Patent: US4373097, 1983, A,
[6] Collection of Czechoslovak Chemical Communications, 1985, vol. 50, # 7, p. 1514 - 1518
[7] Journal of Sulfur Chemistry, 2015, vol. 36, # 2, p. 135 - 144
[8] Patent: US2016/90397, 2016, A1, . Location in patent: Paragraph 0056
[9] Patent: WO2012/82436, 2012, A2, . Location in patent: Page/Page column 179-180
[10] Patent: WO2012/82436, 2012, A2, . Location in patent: Page/Page column 190-191
[11] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, p. 1349 - 1358
[12] Tetrahedron Letters, 1990, vol. 31, # 51, p. 7485 - 7488
[13] Journal of Medicinal Chemistry, 2011, vol. 54, # 21, p. 7734 - 7738
[14] European Journal of Medicinal Chemistry, 2016, vol. 111, p. 84 - 94
[15] Chemistry - A European Journal, 2014, vol. 20, # 18, p. 5397 - 5402
[16] Tetrahedron Letters, 1988, vol. 29, # 45, p. 5729 - 5732
[17] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 22, p. 6239 - 6244
[18] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 5, p. 1484 - 1487
[19] ChemBioChem, 2012, vol. 13, # 8, p. 1167 - 1173
[20] Patent: WO2014/144776, 2014, A1,
[21] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 4, p. 408 - 412
[22] Patent: EP3144001, 2017, A1,
[23] Patent: WO2017/218802, 2017, A1, . Location in patent: Paragraph 00168

2
[ 662131-88-6 ]
[ 892-48-8 ]

Reference： [1] European Journal of Organic Chemistry, 2003, # 24, p. 4748 - 4751
[2] Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 85, # 1-4, p. 149 - 152

3
[ 142031-35-4 ]
[ 892-48-8 ]

Reference： [1] Chemistry and Biology, 2014, vol. 21, # 3, p. 345 - 356

4
[ 69260-62-4 ]
[ 892-48-8 ]

Reference： [1] Canadian Journal of Chemistry, 1991, vol. 69, # 9, p. 1468 - 1474
[2] Collection of Czechoslovak Chemical Communications, 1980, vol. 45, # 2, p. 599 - 605

5
[ 24514-56-5 ]
[ 892-48-8 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, p. 1197 - 1204

6
[ 2004-06-0 ]
[ 892-48-8 ]

Reference： [1] Patent: WO2017/218802, 2017, A1,

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[ CAS No. 892-48-8 ] {[proInfo.proName]}

Quality Control of [ 892-48-8 ]

Related Doc. of [ 892-48-8 ]

Product Details of [ 892-48-8 ]

Calculated chemistry of [ 892-48-8 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 892-48-8 ]

Application In Synthesis of [ 892-48-8 ]

[ 892-48-8 ] Synthesis Path-Upstream 1~6

[ 892-48-8 ] Synthesis Path-Downstream 1~87

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