((2R,3R,4R,5S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-methanol

Base Information

• Chemical Name: ((2R,3R,4R,5S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-methanol
• CAS No.: 300807-58-3
• Molecular Formula: C₂₇H₃₀O₅
• Molecular Weight: 434.532
• Mol file: 300807-58-3.mol

Synonyms:((2R,3R,4R,5S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-methanol

Chemical Property of ((2R,3R,4R,5S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((2R,3R,4R,5S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-methanol

There total 5 articles about ((2R,3R,4R,5S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-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: 92.0%

(2S,3S,4R,5S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-carbaldehyde (287733-95-3) → ((2R,3R,4R,5S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-methanol (300807-58-3)

Guidance literature:

With sodium tetrahydroborate; In ethanol; for 2h;

DOI:10.1021/jo0003908

Reference yield: 39.0%

benzyl bromide (100-39-0) + 3,4-dibenzyloxy-2,5-dihydroxymethyltetrahydrofuran (129115-89-5) → 2,5-anhydro-3,4,6-tri-O-benzyl-D-glucitol (102208-54-8) + ((2R,3R,4R,5S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-methanol (300807-58-3)

Guidance literature:

With silver(l) oxide; In toluene;

DOI:10.1002/anie.200390253

Reference yield:

R,R-3,4-dibenzyloxy-threo-hexa-1,5-diene (111555-72-7) → ((2R,3R,4R,5S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-methanol (300807-58-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / OsO₄; CSA; Me₃NO / CH₂Cl₂

2: 35 percent / Ag₂O / toluene

With osmium(VIII) oxide; trimethylamine-N-oxide; camphor-10-sulfonic acid; silver(l) oxide; In dichloromethane; toluene;

DOI:10.1002/anie.200390253

upstream raw materials:

(2S,3S,4R,5S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-carbaldehyde

benzyl bromide

3,4-dibenzyloxy-2,5-dihydroxymethyltetrahydrofuran

R,R-3,4-dibenzyloxy-threo-hexa-1,5-diene

Downstream raw materials:

Phosphoric acid (2R,3R,4R,5S)-3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-ylmethyl ester diphenyl ester

C₃₀H₃₀O₁₁P₂

Phosphoric acid (2R,3S,4S,5S)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-ylmethyl ester diphenyl ester

D-Fructose-1,6-diphosphat