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

Base Information

• Chemical Name: {2-[(2R,3S,5R)-5-(6-Amino-2-chloro-purin-9-yl)-3-benzyloxy-tetrahydro-furan-2-yl]-1,1-difluoro-ethyl}-phosphonic acid diethyl ester
• CAS No.: 180922-61-6
• Molecular Formula: C₂₂H₂₇ClF₂N₅O₅P
• Molecular Weight: 545.91
• Mol file: 180922-61-6.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about {2-[(2R,3S,5R)-5-(6-Amino-2-chloro-purin-9-yl)-3-benzyloxy-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:

{2-[(2R,3R,4R,5R)-5-(6-Amino-2-chloro-purin-9-yl)-3-benzyloxy-4-phenoxythiocarbonyloxy-tetrahydro-furan-2-yl]-1,1-difluoro-ethyl}-phosphonic acid diethyl ester → {2-[(2R,3S,5R)-5-(6-Amino-2-chloro-purin-9-yl)-3-benzyloxy-tetrahydro-furan-2-yl]-1,1-difluoro-ethyl}-phosphonic acid diethyl ester (180922-61-6)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 80 ℃; for 3h; Yield given;

DOI:10.1055/s-1996-4314

Reference yield:

3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose (63593-02-2) → {2-[(2R,3S,5R)-5-(6-Amino-2-chloro-purin-9-yl)-3-benzyloxy-tetrahydro-furan-2-yl]-1,1-difluoro-ethyl}-phosphonic acid diethyl ester (180922-61-6)

Guidance literature:

Multi-step reaction with 8 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

7: 4-dimethylaminopyridine / CH₂Cl₂ / 1.5 h

8: Bu₃SnH, AIBN / toluene / 3 h / 80 °C

With pyridine; dmap; 2,2'-azobis(isobutyronitrile); ammonia; tri-n-butyl-tin hydride; tin(IV) chloride; acetic acid; In dichloromethane; toluene; acetonitrile;

DOI:10.1055/s-1996-4314

Reference yield:

1,2-O-isopropylidene-3-O-benzyl-α-D-ribofuranoside (70798-12-8) → {2-[(2R,3S,5R)-5-(6-Amino-2-chloro-purin-9-yl)-3-benzyloxy-tetrahydro-furan-2-yl]-1,1-difluoro-ethyl}-phosphonic acid diethyl ester (180922-61-6)

Guidance literature:

Multi-step reaction with 9 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

8: 4-dimethylaminopyridine / CH₂Cl₂ / 1.5 h

9: Bu₃SnH, AIBN / toluene / 3 h / 80 °C

With pyridine; dmap; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); ammonia; tri-n-butyl-tin hydride; tin(IV) chloride; acetic acid; dimethyl sulfoxide; triethylamine; In dichloromethane; toluene; acetonitrile;

DOI:10.1055/s-1996-4314

upstream raw materials:

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

1,2-O-isopropylidene-3-O-benzyl-α-D-ribofuranoside

2,6 dichloropurine

3-O-Benzyl-5,6-dideoxy-6-(diethoxyphosphinyl)-6,6-difluoro-1,2-O-isopropylidene-β-D-ribo-hexofuranose