(2S,3aS,5R,6R,6aR)-6-Benzoyloxy-2-(benzoyloxy-methoxycarbonyl-methyl)-5-(6-hydroxy-purin-9-yl)-hexahydro-furo[3,2-b]furan-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2S,3aS,5R,6R,6aR)-6-Benzoyloxy-2-(benzoyloxy-methoxycarbonyl-methyl)-5-(6-hydroxy-purin-9-yl)-hexahydro-furo[3,2-b]furan-2-carboxylic acid methyl ester
• CAS No.: 107937-52-0
• Molecular Formula: C₃₀H₂₆N₄O₁₁
• Molecular Weight: 618.557
• Mol file: 107937-52-0.mol

Synonyms:

Chemical Property of (2S,3aS,5R,6R,6aR)-6-Benzoyloxy-2-(benzoyloxy-methoxycarbonyl-methyl)-5-(6-hydroxy-purin-9-yl)-hexahydro-furo[3,2-b]furan-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3aS,5R,6R,6aR)-6-Benzoyloxy-2-(benzoyloxy-methoxycarbonyl-methyl)-5-(6-hydroxy-purin-9-yl)-hexahydro-furo[3,2-b]furan-2-carboxylic acid methyl ester

There total 1 articles about (2S,3aS,5R,6R,6aR)-6-Benzoyloxy-2-(benzoyloxy-methoxycarbonyl-methyl)-5-(6-hydroxy-purin-9-yl)-hexahydro-furo[3,2-b]furan-2-carboxylic acid methyl 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:

(2S,3aR,5R,6R,6aS)-6-Benzoyloxy-2-(benzoyloxy-methoxycarbonyl-methyl)-3a-chloro-5-(6-hydroxy-purin-9-yl)-hexahydro-furo[3,2-b]furan-2-carboxylic acid methyl ester → (2S,3aS,5R,6R,6aR)-6-Benzoyloxy-2-(benzoyloxy-methoxycarbonyl-methyl)-5-(6-hydroxy-purin-9-yl)-hexahydro-furo[3,2-b]furan-2-carboxylic acid methyl ester (107937-52-0,120021-21-8)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride;

DOI:10.1248/cpb.36.3760

Reference yield: 69.3%

acetic acid (64-19-7,77671-22-8) + (2S,3aS,5R,6R,6aR)-6-Benzoyloxy-2-(benzoyloxy-methoxycarbonyl-methyl)-5-(6-hydroxy-purin-9-yl)-hexahydro-furo[3,2-b]furan-2-carboxylic acid methyl ester (107937-52-0,120021-21-8) → dimethyl 1'β-acetoxy-O2',O7'-dibenzoyl-1'-deadenino-4'β,5'-dihydrogriseolate (107937-51-9)

Guidance literature:

With sulfuric acid; acetic anhydride; for 14h; Ambient temperature;

DOI:10.1248/cpb.36.3760

Reference yield:

(2S,3aS,5R,6R,6aR)-6-Benzoyloxy-2-(benzoyloxy-methoxycarbonyl-methyl)-5-(6-hydroxy-purin-9-yl)-hexahydro-furo[3,2-b]furan-2-carboxylic acid methyl ester (107937-52-0,120021-21-8) → dimethyl 6-deamino-6-hydroxy-2-acetylamino-2-dehydro-4'β,5'-dihydro-O(2'),O(7')-dibenzoylgriseolate (107937-53-1,120021-22-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 69.3 percent / conc. H₂SO₄, acetic anhydride / 14 h / Ambient temperature

2: 22 percent / trimethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / 96 h / Ambient temperature

With trimethylsilyl trifluoromethanesulfonate; sulfuric acid; acetic anhydride; In 1,2-dichloro-ethane;

DOI:10.1248/cpb.36.3760

Downstream raw materials:

dimethyl 1'β-acetoxy-O^2',O^7'-dibenzoyl-1'-deadenino-4'β,5'-dihydrogriseolate

dimethyl 6-deamino-6-hydroxy-2-acetylamino-2-dehydro-4'β,5'-dihydro-O(2'),O(7')-dibenzoylgriseolate

dimethyl 1'-deadenino-1'β-2-acetylguanin-7-yl>-4'β,5'-dihydro-O^2',O^7'-dibenzoylgriseolate