Acetic acid (1R,2R,3R,4R)-4-(6-benzoylamino-purin-9-yl)-2,3-bis-benzyloxy-cyclopentylmethyl ester

Base Information

• Chemical Name: Acetic acid (1R,2R,3R,4R)-4-(6-benzoylamino-purin-9-yl)-2,3-bis-benzyloxy-cyclopentylmethyl ester
• CAS No.: 149454-97-7
• Molecular Formula: C₃₄H₃₃N₅O₅
• Molecular Weight: 591.667
• Mol file: 149454-97-7.mol

Synonyms:Acetic acid (1R,2R,3R,4R)-4-(6-benzoylamino-purin-9-yl)-2,3-bis-benzyloxy-cyclopentylmethyl ester

Chemical Property of Acetic acid (1R,2R,3R,4R)-4-(6-benzoylamino-purin-9-yl)-2,3-bis-benzyloxy-cyclopentylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (1R,2R,3R,4R)-4-(6-benzoylamino-purin-9-yl)-2,3-bis-benzyloxy-cyclopentylmethyl ester

There total 19 articles about Acetic acid (1R,2R,3R,4R)-4-(6-benzoylamino-purin-9-yl)-2,3-bis-benzyloxy-cyclopentylmethyl 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: 21.0%

Acetic acid (1R,2S,3R,4R,5R)-3-(6-benzoylamino-purin-9-yl)-4,5-bis-benzyloxy-2-nitro-cyclopentylmethyl ester (149454-96-6) → Acetic acid (1R,2R,3R,4R)-4-(6-benzoylamino-purin-9-yl)-2,3-bis-benzyloxy-cyclopentylmethyl ester (149454-97-7)

Guidance literature:

With azobisisobutyronitrile; tri-n-butyl-tin hydride; In toluene; at 110 ℃;

DOI:10.1248/cpb.41.636

Reference yield:

(3S,4R,5R)-3,4-Bis-benzyloxy-5-nitromethyl-tetrahydro-pyran-2-ol → Acetic acid (1R,2R,3R,4R)-4-(6-benzoylamino-purin-9-yl)-2,3-bis-benzyloxy-cyclopentylmethyl ester (149454-97-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / CsF / dimethylformamide / 3 h / 25 °C

2: p-toluenesulfonic acid monohydrate / 0.5 h / 25 °C

3: 85 percent / CsF / dimethylformamide / 1 h

4: 21 percent / tributyltin hydride, 2,2'-azobisisobutyronitrile / toluene / 1 h / Heating

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; toluene-4-sulfonic acid; cesium fluoride; In N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(01)89611-3

Reference yield:

methyl 2,3-di-O-benzyl-β-D-arabinopyranoside (149454-89-7) → Acetic acid (1R,2R,3R,4R)-4-(6-benzoylamino-purin-9-yl)-2,3-bis-benzyloxy-cyclopentylmethyl ester (149454-97-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) (COCl)2, DMSO; 2.) triethylamine / 1.) CH₂Cl₂, -40 deg C, 6 h; 2.) CH₂Cl₂, 25 deg C, 30 min

2: KF, 18-crown-6 / dimethylformamide / 0.5 h / 25 °C

3: p-toluenesulfonic acid monohydrate / 25 °C

4: NaBH₄ / ethanol / 1 h / 25 °C

5: 57 percent / concd. HCl / acetic acid / 30 °C

6: 86 percent / CsF / dimethylformamide / 3 h / 25 °C

7: p-toluenesulfonic acid monohydrate / 0.5 h / 25 °C

8: 85 percent / CsF / dimethylformamide / 1 h

9: 21 percent / tributyltin hydride, 2,2'-azobisisobutyronitrile / toluene / 1 h / Heating

With hydrogenchloride; potassium fluoride; sodium tetrahydroborate; oxalyl dichloride; 18-crown-6 ether; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; cesium fluoride; In ethanol; acetic acid; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(01)89611-3

upstream raw materials:

Acetic acid (1R,2S,3R,4R,5R)-3-(6-benzoylamino-purin-9-yl)-4,5-bis-benzyloxy-2-nitro-cyclopentylmethyl ester

D-arabinopyranose

methyl 2-O-benzyl-3,4-O-isopropylidene-β-D-arabinopyranoside

methyl 2,3-di-O-benzyl-β-D-arabinopyranoside

Downstream raw materials:

[(1R,2R,3R,4R)-4-(6-Amino-purin-9-yl)-2,3-bis-benzyloxy-cyclopentyl]-methanol

(+)-cyclaradine