[(3aS,5S,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methanol

Base Information

• Chemical Name: [(3aS,5S,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methanol
• CAS No.: 391201-57-3
• Molecular Formula: C₁₅H₂₀O₅
• Molecular Weight: 280.321

Synonyms:[(3aS,5S,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methanol

Chemical Property of [(3aS,5S,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methanol

Chemical Property:

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Technology Process of [(3aS,5S,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methanol

There total 15 articles about [(3aS,5S,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methanol 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%

3-O-benzyl-1,2-O-isopropylidene-5-O-triisopropylsilyl-α-L-xylofuranose (391201-56-2) → [(3aS,5S,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methanol (391201-57-3)

Guidance literature:

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

DOI:10.1016/S0040-4020(01)00885-7

Reference yield: 97.0%

{[(3aS,5S,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methoxy}(tert-butyl)dimethylsilane → [(3aS,5S,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methanol (391201-57-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 1h;

DOI:10.1055/s-0037-1610997

Reference yield: 83.0%

(3aS,5S,6R,6aS)-6-Benzyloxy-2,2-dimethyl-5-trityloxymethyl-tetrahydro-furo[2,3-d][1,3]dioxole (528593-79-5) → [(3aS,5S,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methanol (391201-57-3)

Guidance literature:

With hydrogen bromide; acetic acid; at 10 ℃; for 0.0166667h;

DOI:10.1016/S0957-4166(02)00752-8

upstream raw materials:

3-O-benzyl-1,2-O-isopropylidene-5-O-triisopropylsilyl-α-L-xylofuranose

(3aS,5S,6R,6aS)-6-Benzyloxy-2,2-dimethyl-5-trityloxymethyl-tetrahydro-furo[2,3-d][1,3]dioxole

β-L-arabinose

1,2-O-Isopropylidene-5-O-triphenylmethyl-α-L-xylofuranose

Downstream raw materials:

3-O-benzyl-1,2-O-isopropylidene-5-O-trifluoromethanesulfonyl-α-L-xylofuranose

(3aS,5R,6R,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde

diethyl (4S)-(1,3-di-O-acetyl-2-O-benzyl-α-L-threofuranos-4-yl)phosphonate

diethyl (4S)-(1,3-di-O-acetyl-2-O-benzoyl-α-L-threofuranos-4-yl)phosphonate

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