3-O-benzyl-5-O-tert-butyldiphenylsilyl-4-C-methyl-1,2-O-isopropylidene-α-D-ribofuranose

Base Information

• Chemical Name: 3-O-benzyl-5-O-tert-butyldiphenylsilyl-4-C-methyl-1,2-O-isopropylidene-α-D-ribofuranose
• CAS No.: 860651-64-5
• Molecular Formula: C₃₂H₄₀O₅Si
• Molecular Weight: 532.752

Synonyms:3-O-benzyl-5-O-tert-butyldiphenylsilyl-4-C-methyl-1,2-O-isopropylidene-α-D-ribofuranose

Chemical Property of 3-O-benzyl-5-O-tert-butyldiphenylsilyl-4-C-methyl-1,2-O-isopropylidene-α-D-ribofuranose

Chemical Property:

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Technology Process of 3-O-benzyl-5-O-tert-butyldiphenylsilyl-4-C-methyl-1,2-O-isopropylidene-α-D-ribofuranose

There total 2 articles about 3-O-benzyl-5-O-tert-butyldiphenylsilyl-4-C-methyl-1,2-O-isopropylidene-α-D-ribofuranose 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: 96.0%

((3aR,5R,6S,6aR)-6-Benzyloxy-5-iodomethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethoxy)-tert-butyl-diphenyl-silane (860651-67-8) → 3-O-benzyl-5-O-tert-butyldiphenylsilyl-4-C-methyl-1,2-O-isopropylidene-α-D-ribofuranose (860651-64-5)

Guidance literature:

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

DOI:10.1055/s-2005-865328

Reference yield:

{3-[(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)methyl]-(1S,3R,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)bicyclo[3.3.0]oct-3-yl}methan-1-ol (212970-72-4) → 3-O-benzyl-5-O-tert-butyldiphenylsilyl-4-C-methyl-1,2-O-isopropylidene-α-D-ribofuranose (860651-64-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / I₂; PPh₃; imidazole / benzene / 5 h / Heating

2: 96 percent / AIBN; n-Bu₃SnH / toluene / Heating

With 1H-imidazole; 2,2'-azobis(isobutyronitrile); iodine; tri-n-butyl-tin hydride; triphenylphosphine; In toluene; benzene;

DOI:10.1055/s-2005-865328

Reference yield: 79.0%

3-O-benzyl-5-O-tert-butyldiphenylsilyl-4-C-methyl-1,2-O-isopropylidene-α-D-ribofuranose (860651-64-5) + acetic anhydride (108-24-7) → 1,2-di-O-acetyl-3-O-benzyl-5-O-tert-butyldiphenylsilyl-4-C-methyl-α,β-D-ribofuranose (860651-65-6)

Guidance literature:

With sulfuric acid; acetic acid; at 20 ℃; for 16h;

DOI:10.1055/s-2005-865328

upstream raw materials:

((3aR,5R,6S,6aR)-6-Benzyloxy-5-iodomethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethoxy)-tert-butyl-diphenyl-silane

{3-[(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)methyl]-(1S,3R,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)bicyclo[3.3.0]oct-3-yl}methan-1-ol

Downstream raw materials:

1,2-di-O-acetyl-3-O-benzyl-5-O-tert-butyldiphenylsilyl-4-C-methyl-α,β-D-ribofuranose

3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-2'-deoxy-4'-C-methyluridine

2'-deoxy-5'-O-dimethoxytrityl-4'-C-methyluridine

2'-O-acetyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-4'-C-methyluridine

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