{2-[(2R,3S,4R,5R)-5-(6-Amino-2-chloro-purin-9-yl)-3-benzyloxy-4-hydroxy-tetrahydro-furan-2-yl]-1,1-difluoro-ethyl}-phosphonic acid diethyl ester

Base Information

Chemical Name:{2-[(2R,3S,4R,5R)-5-(6-Amino-2-chloro-purin-9-yl)-3-benzyloxy-4-hydroxy-tetrahydro-furan-2-yl]-1,1-difluoro-ethyl}-phosphonic acid diethyl ester
CAS No.:180922-57-0
Molecular Formula:C₂₂H₂₇ClF₂N₅O₆P
Molecular Weight:561.91
Hs Code.:

Synonyms:{2-[(2R,3S,4R,5R)-5-(6-Amino-2-chloro-purin-9-yl)-3-benzyloxy-4-hydroxy-tetrahydro-furan-2-yl]-1,1-difluoro-ethyl}-phosphonic acid diethyl ester

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Chemical Property of {2-[(2R,3S,4R,5R)-5-(6-Amino-2-chloro-purin-9-yl)-3-benzyloxy-4-hydroxy-tetrahydro-furan-2-yl]-1,1-difluoro-ethyl}-phosphonic acid diethyl ester

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Technology Process of {2-[(2R,3S,4R,5R)-5-(6-Amino-2-chloro-purin-9-yl)-3-benzyloxy-4-hydroxy-tetrahydro-furan-2-yl]-1,1-difluoro-ethyl}-phosphonic acid diethyl ester

There total 9 articles about {2-[(2R,3S,4R,5R)-5-(6-Amino-2-chloro-purin-9-yl)-3-benzyloxy-4-hydroxy-tetrahydro-furan-2-yl]-1,1-difluoro-ethyl}-phosphonic acid diethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 59.0%

: Benzoic acid (2R,3R,4R,5R)-4-benzyloxy-2-[2-chloro-6-(trimethylsilanyl-amino)-purin-9-yl]-5-[2-(diethoxy-phosphoryl)-2,2-difluoro-ethyl]-tetrahydro-furan-3-yl ester

: 180922-57-0
{2-[(2R,3S,4R,5R)-5-(6-Amino-2-chloro-purin-9-yl)-3-benzyloxy-4-hydroxy-tetrahydro-furan-2-yl]-1,1-difluoro-ethyl}-phosphonic acid diethyl ester

Guidance literature:: With ammonia; at -78 - 20 ℃;
DOI:10.1055/s-1996-4314

Reference yield:

: 63593-02-2
3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose

: 180922-57-0
{2-[(2R,3S,4R,5R)-5-(6-Amino-2-chloro-purin-9-yl)-3-benzyloxy-4-hydroxy-tetrahydro-furan-2-yl]-1,1-difluoro-ethyl}-phosphonic acid diethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) THF, -78 deg C, 6 h, 2.) THF, -78 deg C, 45 min

2: 71 percent / azobisisobutyronitrile, Bu₃SnH / toluene / 2.5 h / Heating

3: 54 percent / 60percent aq. AcOH / 1 h / 100 °C

4: 57 percent / pyridine / 0.75 h / Ambient temperature

5: SnCl₄ / acetonitrile / 0.75 h / Ambient temperature

6: 59 percent / liquid NH₃ / -78 - 20 °C

With pyridine; 2,2'-azobis(isobutyronitrile); ammonia; tri-n-butyl-tin hydride; tin(IV) chloride; acetic acid; In toluene; acetonitrile;
DOI:10.1055/s-1996-4314

Reference yield:

: 70798-12-8
1,2-O-isopropylidene-3-O-benzyl-α-D-ribofuranoside

: 180922-57-0
{2-[(2R,3S,4R,5R)-5-(6-Amino-2-chloro-purin-9-yl)-3-benzyloxy-4-hydroxy-tetrahydro-furan-2-yl]-1,1-difluoro-ethyl}-phosphonic acid diethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, from -78 deg C to RT

2: 1.) THF, -78 deg C, 6 h, 2.) THF, -78 deg C, 45 min

3: 71 percent / azobisisobutyronitrile, Bu₃SnH / toluene / 2.5 h / Heating

4: 54 percent / 60percent aq. AcOH / 1 h / 100 °C

5: 57 percent / pyridine / 0.75 h / Ambient temperature

6: SnCl₄ / acetonitrile / 0.75 h / Ambient temperature

7: 59 percent / liquid NH₃ / -78 - 20 °C

With pyridine; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); ammonia; tri-n-butyl-tin hydride; tin(IV) chloride; acetic acid; dimethyl sulfoxide; triethylamine; In toluene; acetonitrile;
DOI:10.1055/s-1996-4314