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

Base Information

• Chemical Name: 2-azido-2-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-yl)ethanol
• CAS No.: 881894-81-1
• Molecular Formula: C₁₆H₂₁N₃O₅
• Molecular Weight: 335.36

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

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

Chemical Property:

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

There total 11 articles about 2-azido-2-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-yl)ethanol 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: 97.0%

5-azido-3-O-benzyl-5-deoxy-1,2-O-isopropylidene-6-O-pivaloyl-β-L-idofuranose (1253932-16-9) → 2-azido-2-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-yl)ethanol (881894-81-1)

Guidance literature:

With methanol; sodium methylate; at 20 ℃; for 96h;

DOI:10.1055/s-0029-1218850

Reference yield: 91.0%

[(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 (881895-07-4) → 2-azido-2-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-yl)ethanol (881894-81-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1021/ol0601996

Reference yield: 80.0%

[2-azido-2-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethoxy]-tert-butyl dimethylsilane (888954-89-0) → 2-azido-2-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-yl)ethanol (881894-81-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.1055/s-2006-926369

upstream raw materials:

[(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

[2-azido-2-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethoxy]-tert-butyl dimethylsilane

methanesulfonic acid (6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyldimethylsiloxy)ethyl ester

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

Downstream raw materials:

1,5-dideoxy-1,5-imino-D-glucitol

[1-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-hydroxyethyl]carbamic acid benzyl ester

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

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