[ CAS No. 38819-10-2 ] {[proInfo.proName]}

Name: 38819-10-2|9-beta-Arabinosylguanine|98%
Brand: Ambeed
SKU: A172052
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2D 3D

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Quality Control of [ 38819-10-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 38819-10-2 ]

SDS Specification

Alternatived Products of [ 38819-10-2 ]

Product Details of [ 38819-10-2 ]

CAS No. :	38819-10-2	MDL No. :	MFCD00065486
Formula :	C₁₀H₁₃N₅O₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NYHBQMYGNKIUIF-FJFJXFQQSA-N
M.W :	283.24	Pubchem ID :	135499520
Synonyms :	AraG;ara-Guanosine;Ara-G , ara-Guanosine, Guanine Arabinoside;NSC 76352;Guanine Arabinoside

Calculated chemistry of [ 38819-10-2 ]

Physicochemical Properties

Num. heavy atoms :	20
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.5
Num. rotatable bonds :	2
Num. H-bond acceptors :	7.0
Num. H-bond donors :	5.0
Molar Refractivity :	65.5
TPSA :	159.51 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) :	-9.37 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.64
Log Po/w (XLOGP3) :	-1.89
Log Po/w (WLOGP) :	-3.0
Log Po/w (MLOGP) :	-1.95
Log Po/w (SILICOS-IT) :	-2.22
Consensus Log Po/w :	-1.68

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.61
Solubility :	70.1 mg/ml ; 0.248 mol/l
Class :	Very soluble
Log S (Ali) :	-0.94
Solubility :	32.5 mg/ml ; 0.115 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	0.51
Solubility :	910.0 mg/ml ; 3.21 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 38819-10-2 ]

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 [ 38819-10-2 ]

* 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 [ 38819-10-2 ]

[ 38819-10-2 ] Synthesis Path-Downstream 1~88

1
[ 38819-10-2 ]
[ 59981-79-2 ]

Reference： [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1899 - 1903
[2]Biochemical Pharmacology,1995,vol. 50,p. 163 - 168

2
[ 69304-44-5 ]
[ 38819-10-2 ]
[ 90813-68-6 ]

Reference： [1]Tetrahedron,1984,vol. 40,p. 125 - 135

3
[ 38819-10-2 ]
[ 108-24-7 ]
[ 74491-89-7 ]

Reference： [1]Helvetica Chimica Acta,1993,vol. 76,p. 158 - 167

4
[ 120595-74-6 ]
[ 38819-10-2 ]

Reference： [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1899 - 1903

5
[ 99691-93-7 ]
[ 38819-10-2 ]

Reference： [1]Pharmaceutical Chemistry Journal,1985,vol. 19,p. 259 - 261
Khimiko-Farmatsevticheskii Zhurnal,1985,vol. 19,p. 425 - 427

6
[ 148313-05-7 ]
[ 38819-10-2 ]

Reference： [1]Helvetica Chimica Acta,1994,vol. 77,p. 429 - 434

7
[ 34079-68-0 ]
[ 38819-10-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 4210 - 4212
[2]Canadian Journal of Chemistry,1997,vol. 75,p. 762 - 767
[3]Nucleosides and Nucleotides,1997,vol. 16,p. 1645 - 1647

8
[ 38819-10-2 ]
[ 79-30-1 ]
[ 199601-35-9 ]

Reference： [1]Nucleosides and Nucleotides,1997,vol. 16,p. 1645 - 1647

9
[ 129835-17-2 ]
[ 38819-10-2 ]

Yield	Reaction Conditions	Operation in experiment
59%	With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20℃; for 12h;Inert atmosphere;	[0230] To a solution of PH- 13 (50 g, 95.10mmol, 1.00equiv) in tetrahydrofuran (500 mL) with an inert atmosphere of nitrogen, was added tetrabutylammonium fluoride (95 mL, 1.00equiv, 1N in tetrahydrofuran). The resulting mixture was stirred for 12 h at 20oC. The resulting mixture was concentrated under reduced pressure. The crude was re-crystallized from methanol/ethyl acetate in the ratio of 1/5 (20 ml/g) three times. The solids were collected by filtration, and then purified by Flash with the following conditions: Column, C18 silica gel; mobile phase, waters and acetonitrile (2% acetonitrile up to 10% in 10 min); Detector, UV 254 nm. This resulted in 16 g (59%) of PH- 14 as a brown solid.1H-NMR (DMSO-d6, 400MHz): 10.44(s, 1H), 6.49(s, 2H), 6.02(s, 1H), 5.55-5.65(m, 2H), 5.10(s, 1H), 4.08(m, 2H), 3.76(m, 1H), 3.64(m, 1H).
59%	With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20℃; for 12h;Inert atmosphere;	To a solution of PH- 13 (50 g, 95.l0mmol, l .OOequiv) in tetrahydrofuran (500 mL) with an inert atmosphere of nitrogen, was added tetrabutylammonium fluoride (95 mL, l .OOequiv, 1N in tetrahydrofuran). The resulting mixture was stirred for 12 h at 20C. The resulting mixture was concentrated under reduced pressure. The crude was re-crystallized from methanol/ethyl acetate in the ratio of 1/5 (20 ml/g) three times. The solids were collected by filtration, and then purified by Plash with the following conditions: Column, Cl 8 silica gel; mobile phase, waters and acetonitrile (2% acetonitrile up to 10% in 10 min); Detector, UV 254 nm. This resulted in 16 g (59%) of PH- 14 as a brown solid. 1H-NMR (DMSO-i/e, 400MHz): l0.44(s, 1H), 6.49(s, 2H), 6.02(s, 1H), 5.55- 5.65(m, 2H), 5T0(s, 1H), 4.08(m, 2H), 3.76(m, 1H), 3.64(m, 1H).

Reference： [1]Patent: WO2018/53185,2018,A1 .Location in patent: Paragraph 0230
[2]Patent: WO2019/175260,2019,A2 .Location in patent: Paragraph 0241
[3]Nucleosides and Nucleotides,1999,vol. 18,p. 137 - 151

11
[ 38819-10-2 ]
[ 69304-37-6 ]
[ 129835-17-2 ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 9909 - 9918
[2]Journal of Organic Chemistry,2010,vol. 75,p. 637 - 641

12
[ 38819-10-2 ]
[ 908371-58-4 ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 9909 - 9918

13
[ 38819-10-2 ]
[ 908371-51-7 ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 9909 - 9918

14
[ 38819-10-2 ]
N²,N²-diacetyl-9-[2'-O-acetyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl]guanine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 9909 - 9918

15
[ 38819-10-2 ]
[ 908371-57-3 ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 9909 - 9918

16
[ 38819-10-2 ]
[ 908371-55-1 ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 9909 - 9918

17
[ 38819-10-2 ]
[ 908371-59-5 ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 9909 - 9918

18
[ 38819-10-2 ]
[ 908371-53-9 ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 9909 - 9918

19
[ 38819-10-2 ]
[ 908371-60-8 ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 9909 - 9918

20
[ 38819-10-2 ]
N²-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-methylselenoguanosine 3'-(2-cyanoethyl diisopropylphosphoramidite) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 9909 - 9918

21
[ 69304-44-5 ]
[ 38819-10-2 ]

Reference： [1]Nucleosides and Nucleotides,1999,vol. 18,p. 137 - 151
[2]Patent: WO2018/53185,2018,A1

22
[ 118-00-3 ]
[ 38819-10-2 ]

Reference： [1]Nucleosides and Nucleotides,1999,vol. 18,p. 137 - 151
[2]Patent: WO2018/53185,2018,A1
[3]Patent: WO2019/175260,2019,A2

23
[ 221092-57-5 ]
[ 38819-10-2 ]

Reference： [1]Nucleosides and Nucleotides,1999,vol. 18,p. 137 - 151

24
[ 142941-91-1 ]
[ 38819-10-2 ]

Reference： [1]Nucleosides and Nucleotides,1999,vol. 18,p. 137 - 151
[2]Patent: WO2018/53185,2018,A1

25
[ 38819-10-2 ]
[ 78842-13-4 ]

Reference： [1]Nucleosides and Nucleotides,1997,vol. 16,p. 1645 - 1647
[2]Nucleosides and Nucleotides,1997,vol. 16,p. 1645 - 1647

26
[ 38819-10-2 ]
[ 146954-68-9 ]

Reference： [1]Nucleosides and Nucleotides,1997,vol. 16,p. 1645 - 1647
[2]Nucleosides and Nucleotides,1997,vol. 16,p. 1645 - 1647

27
[ 38819-10-2 ]
[ 146954-69-0 ]

Reference： [1]Nucleosides and Nucleotides,1997,vol. 16,p. 1645 - 1647
[2]Nucleosides and Nucleotides,1997,vol. 16,p. 1645 - 1647

28
[ 38819-10-2 ]
[ 200404-37-1 ]

Reference： [1]Nucleosides and Nucleotides,1997,vol. 16,p. 1645 - 1647
[2]Nucleosides and Nucleotides,1997,vol. 16,p. 1645 - 1647

29
[ 38819-10-2 ]
[ 160684-49-1 ]

Reference： [1]Nucleosides and Nucleotides,1997,vol. 16,p. 1645 - 1647

30
[ 38819-10-2 ]
[ 160684-47-9 ]

Reference： [1]Nucleosides and Nucleotides,1997,vol. 16,p. 1645 - 1647

31
[ 38819-10-2 ]
Acetic acid (2R,3S,4R,5R)-2-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-4-(tetrahydro-pyran-2-yloxy)-5-(tetrahydro-pyran-2-yloxymethyl)-tetrahydro-furan-3-yl ester [ No CAS ]

Reference： [1]Nucleosides and Nucleotides,1997,vol. 16,p. 1645 - 1647

32
[ 38819-10-2 ]
[ 160684-48-0 ]

Reference： [1]Nucleosides and Nucleotides,1997,vol. 16,p. 1645 - 1647

33
[ 24880-52-2 ]
[ 38819-10-2 ]

Reference： [1]Nucleosides and Nucleotides,1997,vol. 16,p. 1645 - 1647

34
[ 91592-85-7 ]
[ 38819-10-2 ]

Reference： [1]Helvetica Chimica Acta,1994,vol. 77,p. 429 - 434

35
[ 148313-06-8 ]
[ 38819-10-2 ]

Reference： [1]Helvetica Chimica Acta,1994,vol. 77,p. 429 - 434

36
[ 158604-45-6 ]
[ 38819-10-2 ]

Reference： [1]Helvetica Chimica Acta,1994,vol. 77,p. 429 - 434

37
[ 38819-10-2 ]
9-<5'-O-(monomethoxytrityl)-2'-O-<2-(4-nitrophenyl)ethoxycarbonyl>-β-D-arabinofuranosyl>-N²-<2-(4-nitrophenyl)ethoxycarbonyl>-O⁶-<2-(4-nitrophenyl)ethyl>guanine 3'-(2-cyanoethoxy N,N-diisopropylphosphoramidite) [ No CAS ]

Reference： [1]Helvetica Chimica Acta,1993,vol. 76,p. 158 - 167
[2]Helvetica Chimica Acta,1993,vol. 76,p. 158 - 167

38
[ 38819-10-2 ]
9-<5'-O-(dimethoxytrityl)-2'-O-<2-(4-nitrophenyl)ethoxycarbonyl>-β-D-arabinofuranosyl>-N²-<2-(4-nitrophenyl)ethoxycarbonyl>-O⁶-<2-(4-nitrophenyl)ethyl>guanine 3'-(2-cyanoethoxy N,N-diisopropylphosphoramidite) [ No CAS ]

Reference： [1]Helvetica Chimica Acta,1993,vol. 76,p. 158 - 167
[2]Helvetica Chimica Acta,1993,vol. 76,p. 158 - 167

39
[ 38819-10-2 ]
[ 148313-05-7 ]

Reference： [1]Helvetica Chimica Acta,1993,vol. 76,p. 158 - 167

40
[ 38819-10-2 ]
[ 148313-06-8 ]

Reference： [1]Helvetica Chimica Acta,1993,vol. 76,p. 158 - 167

41
[ 38819-10-2 ]
[ 148313-08-0 ]

Reference： [1]Helvetica Chimica Acta,1993,vol. 76,p. 158 - 167

42
[ 38819-10-2 ]
[ 148313-07-9 ]

Reference： [1]Helvetica Chimica Acta,1993,vol. 76,p. 158 - 167

43
[ 38819-10-2 ]
[ 148313-10-4 ]

Reference： [1]Helvetica Chimica Acta,1993,vol. 76,p. 158 - 167
[2]Helvetica Chimica Acta,1993,vol. 76,p. 158 - 167

44
[ 38819-10-2 ]
[ 148313-09-1 ]

Reference： [1]Helvetica Chimica Acta,1993,vol. 76,p. 158 - 167
[2]Helvetica Chimica Acta,1993,vol. 76,p. 158 - 167

45
[ 38819-10-2 ]
[ 148313-14-8 ]

Reference： [1]Helvetica Chimica Acta,1993,vol. 76,p. 158 - 167
[2]Helvetica Chimica Acta,1993,vol. 76,p. 158 - 167

46
[ 38819-10-2 ]
[ 148313-18-2 ]

Reference： [1]Helvetica Chimica Acta,1993,vol. 76,p. 158 - 167
[2]Helvetica Chimica Acta,1993,vol. 76,p. 158 - 167

47
[ 38819-10-2 ]
Acetic acid (2R,3S,4R,5R)-4-acetoxy-5-acetoxymethyl-2-{2-amino-6-[2-(4-nitro-phenyl)-ethoxy]-purin-9-yl}-tetrahydro-furan-3-yl ester [ No CAS ]

Reference： [1]Helvetica Chimica Acta,1993,vol. 76,p. 158 - 167

48
[ 78131-46-1 ]
[ 38819-10-2 ]

Reference： [1]Pharmaceutical Chemistry Journal,1985,vol. 19,p. 259 - 261
Khimiko-Farmatsevticheskii Zhurnal,1985,vol. 19,p. 425 - 427

49
[ 4060-34-8 ]
[ 38819-10-2 ]

Reference： [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1899 - 1903

50
[ 35085-24-6 ]
[ 38819-10-2 ]

Reference： [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1899 - 1903

51
[ 10310-21-1 ]
[ 38819-10-2 ]

Reference： [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1899 - 1903

52
[ 3083-77-0 ]
[ 118-00-3 ]
[ 38819-10-2 ]

Reference： [1]Process Biochemistry,2012,vol. 47,p. 2182 - 2188

53
[ 38819-10-2 ]
[ 18162-48-6 ]
C₁₆H₂₇N₅O₅Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89.8%	With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20℃; for 18h;	To a stirred solution of compound 15-1 (5.0 g, 17.7 mmol) in dry DMF (30 mL) were added imidazole (2.4 mL, 35.4 mmol) and TBSCl (5.3 g, 35.4 mmol) at 0° C. The mixture was then stirred at R.T. for 18 hour. The reaction mixture was cooled to 0° C. and quenched with ice water. The resulting precipitate was collected and washed with water and acetone to give compound 15-2 (6.3 g, yield 89.8percent) as a white solid. 1H NMR (DMSO-d6, 400 MHz) delta 10.58 (s, 1H), 7.69 (s, 1H), 6.46 (s, 2H), 5.99 (d, J=4.4 Hz, 1H), 5.62 (d, J=4.8 Hz, 1H), 5.52 (d, J=4.4 Hz, 1H), 4.04-4.09 (m, 2H), 3.71-3.85 (m, 2H), 0.88 (s, 9H), 0.04 (s, 6H); ESI-MS: m/z=398 [M+H]+.

Reference： [1]Patent: US9346848,2016,B2 .Location in patent: Page/Page column 129; 130

54
[ 38819-10-2 ]
C₃₀H₂₈N₈O₆ [ No CAS ]

Reference： [1]Patent: US9346848,2016,B2

55
[ 38819-10-2 ]
C₃₀H₃₅N₅O₇Si [ No CAS ]

Reference： [1]Patent: US9346848,2016,B2

56
[ 38819-10-2 ]
C₂₄H₂₁N₅O₇ [ No CAS ]

Reference： [1]Patent: US9346848,2016,B2

57
[ 38819-10-2 ]
C₂₄H₂₀IN₅O₆ [ No CAS ]

Reference： [1]Patent: US9346848,2016,B2

58
[ 38819-10-2 ]
C₄₄H₃₆IN₅O₇ [ No CAS ]

Reference： [1]Patent: US9346848,2016,B2

59
[ 38819-10-2 ]
C₃₀H₂₇N₅O₅ [ No CAS ]

Reference： [1]Patent: US9346848,2016,B2

60
[ 38819-10-2 ]
C₃₀H₂₇IN₈O₅ [ No CAS ]

Reference： [1]Patent: US9346848,2016,B2

61
[ 38819-10-2 ]
4’-azidoarabinoguanosine [ No CAS ]

Reference： [1]Patent: US9346848,2016,B2

62
[ 38819-10-2 ]
C₄₄H₃₅N₅O₇ [ No CAS ]

Reference： [1]Patent: US9346848,2016,B2

63
[ 38819-10-2 ]
C₄₄H₃₅IN₈O₇ [ No CAS ]

Reference： [1]Patent: US9346848,2016,B2

64
[ 38819-10-2 ]
C₁₀H₁₁N₅O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%		[0231] To solution of PH-14 (220 g, 776.72mmol, 1.00equiv) in N,N-dimethylformamide (2000 mL) with an inert atmosphere of argon, was added triphenylphosphine (509 g, 1.94mol, 2.50equiv). The resulting solution was stirred for 1.5 h at 0oC. To this was added diethyl azodicarboxylate (338 g, 1.94mol, 2.50equiv) dropwise with stirring at 0oC. The resulting solution was stirred for 2 h at room temperature. The resulting mixture was poured into 20 L cold ethyl ether. The solids were collected by filtration, then re-crystallized from methanol/ ethyl acetate in the ratio of 1/10 (10 ml/g). This resulted in 100 g (49%) of PH-15 as a brown solid. MS m/z [M+H]+ (ESI): 266.
49%		To solution of PH-14 (220 g, 776.72mmol, 1.OOequiv) in N,N-dimethylformamide (2000 mL) with an inert atmosphere of argon, was added triphenylphosphine (509 g, l .94mol, 2.50equiv). The resulting solution was stirred for 1.5 h at 0C. To this was added diethyl azodicarboxylate (338 g, l .94mol, 2.50equiv) dropwise with stirring at 0C. The resulting solution was stirred for 2 h at room temperature. The resulting mixture was poured into 20 L cold ethyl ether. The solids were collected by filtration, then re-crystallized from methanol/ ethyl acetate in the ratio of 1/10 (10 ml/g). This resulted in 100 g (49%) of PH-15 as a brown solid. MS m/z [M+H]+ (ESI): 266.

Reference： [1]Patent: WO2018/53185,2018,A1 .Location in patent: Paragraph 0231
[2]Patent: WO2019/175260,2019,A2 .Location in patent: Paragraph 0243

65
[ 38819-10-2 ]
C₁₆H₂₅N₅O₄Si [ No CAS ]

Reference： [1]Patent: WO2018/53185,2018,A1

66
[ 38819-10-2 ]
C₂₀H₃₁N₅O₅Si [ No CAS ]

Reference： [1]Patent: WO2018/53185,2018,A1

67
[ 38819-10-2 ]
C₂₀H₃₂N₈O₅Si [ No CAS ]
C₂₀H₃₂N₈O₅Si [ No CAS ]

Reference： [1]Patent: WO2018/53185,2018,A1

68
[ 38819-10-2 ]
C₂₁H₃₁F₃N₈O₇SSi [ No CAS ]
C₂₁H₃₁F₃N₈O₇SSi [ No CAS ]

Reference： [1]Patent: WO2018/53185,2018,A1
[2]Patent: WO2019/175260,2019,A2

69
[ 38819-10-2 ]
C₁₄H₁₇FN₈O₄ [ No CAS ]
C₁₄H₁₇FN₈O₄ [ No CAS ]

Reference： [1]Patent: WO2018/53185,2018,A1
[2]Patent: WO2019/175260,2019,A2

70
[ 38819-10-2 ]
C₁₄H₁₉FN₆O₄ [ No CAS ]

Reference： [1]Patent: WO2018/53185,2018,A1
[2]Patent: WO2019/175260,2019,A2

71
[ 38819-10-2 ]
C₃₄H₃₅FN₆O₅ [ No CAS ]

Reference： [1]Patent: WO2018/53185,2018,A1
[2]Patent: WO2019/175260,2019,A2

72
[ 38819-10-2 ]
C₄₃H₅₂FN₈O₆P [ No CAS ]

Reference： [1]Patent: WO2018/53185,2018,A1
[2]Patent: WO2019/175260,2019,A2

73
[ 38819-10-2 ]
C₁₀H₁₂Cl₂N₅O₆P [ No CAS ]

Reference： [1]ChemMedChem,2018,vol. 13,p. 2305 - 2316

74
[ 38819-10-2 ]
C₂₆H₄₄N₇O₁₀P [ No CAS ]

Reference： [1]ChemMedChem,2018,vol. 13,p. 2305 - 2316

75
[ 38819-10-2 ]
[ 20535-83-5 ]
9-(β-D-Arabinofuranosyl)-2-amino-6-methoxy-9H-purine [ No CAS ]