3-O-benzyl-6-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-α-D-glucofuranose

Base Information

• Chemical Name: 3-O-benzyl-6-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-α-D-glucofuranose
• CAS No.: 369630-58-0
• Molecular Formula: C₃₂H₄₀O₆Si
• Molecular Weight: 548.751

Synonyms:3-O-benzyl-6-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-α-D-glucofuranose

Chemical Property of 3-O-benzyl-6-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-α-D-glucofuranose

Chemical Property:

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Technology Process of 3-O-benzyl-6-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-α-D-glucofuranose

There total 1 articles about 3-O-benzyl-6-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-α-D-glucofuranose 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: 98.0%

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol (22529-61-9) + tert-butylchlorodiphenylsilane (58479-61-1) → 3-O-benzyl-6-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-α-D-glucofuranose (369630-58-0)

Guidance literature:

With pyridine; at 20 ℃; for 3h;

DOI:10.1021/ol0601996

Reference yield: 99.0%

3-O-benzyl-6-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-α-D-glucofuranose (369630-58-0) + methyl iodide (74-88-4) → 3-O-benzyl-6-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-5-O-methyl-α-D-glucofuranose (1169442-88-9)

Guidance literature:

3-O-benzyl-6-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-α-D-glucofuranose; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃;

methyl iodide; With tetrabutylammomium bromide; In tetrahydrofuran; mineral oil; at 0 - 20 ℃;

DOI:10.1016/j.tetasy.2009.03.004

Reference yield: 93.0%

trifluoromethylsulfonic anhydride (358-23-6) + 3-O-benzyl-6-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-α-D-glucofuranose (369630-58-0) → Trifluoro-methanesulfonic acid (R)-1-((3aR,5S,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyl-diphenyl-silanyloxy)-ethyl ester (881895-06-3)

Guidance literature:

With pyridine; In dichloromethane; for 0.5h;

DOI:10.1021/ol0601996

upstream raw materials:

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

tert-butylchlorodiphenylsilane

Downstream raw materials:

1-((3aR,5S,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyl-diphenyl-silanyloxy)-ethanone

Trifluoro-methanesulfonic acid (R)-1-((3aR,5S,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyl-diphenyl-silanyloxy)-ethyl ester

2-azido-2-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-yl)ethanol

[(S)-2-Azido-2-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethoxy]-tert-butyl-diphenyl-silane

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