(1S,2R,3R,4R)-1-O-benzoyl-2,3-di-O-benzyl-4-benzyloxymethylcyclohex-5-ene-1,2,3-triol

Base Information

• Chemical Name: (1S,2R,3R,4R)-1-O-benzoyl-2,3-di-O-benzyl-4-benzyloxymethylcyclohex-5-ene-1,2,3-triol
• CAS No.: 151693-61-7
• Molecular Formula: C₃₅H₃₄O₅
• Molecular Weight: 534.652
• Mol file: 151693-61-7.mol

Synonyms:(1S,2R,3R,4R)-1-O-benzoyl-2,3-di-O-benzyl-4-benzyloxymethylcyclohex-5-ene-1,2,3-triol

Chemical Property of (1S,2R,3R,4R)-1-O-benzoyl-2,3-di-O-benzyl-4-benzyloxymethylcyclohex-5-ene-1,2,3-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,3R,4R)-1-O-benzoyl-2,3-di-O-benzyl-4-benzyloxymethylcyclohex-5-ene-1,2,3-triol

There total 30 articles about (1S,2R,3R,4R)-1-O-benzoyl-2,3-di-O-benzyl-4-benzyloxymethylcyclohex-5-ene-1,2,3-triol 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: 93.0%

benzoic acid (65-85-0,8013-63-6) + (1R,2R,3R,4R)-2,3-di-O-benzyl-4-benzyloxymethylcyclohex-5-ene-1,2,3-triol (161596-04-9) → (1S,2R,3R,4R)-1-O-benzoyl-2,3-di-O-benzyl-4-benzyloxymethylcyclohex-5-ene-1,2,3-triol (151693-61-7)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In toluene; at 0 ℃; for 0.5h;

DOI:10.1039/c39930000995

Reference yield: 80.0%

benzoyl chloride (98-88-4) + (1S,2R,3R,4R)-2,3-di-O-benzyl-4-benzyloxymethylcyclohex-5-ene-1,2,3-triol (161596-05-0) → (1S,2R,3R,4R)-1-O-benzoyl-2,3-di-O-benzyl-4-benzyloxymethylcyclohex-5-ene-1,2,3-triol (151693-61-7)

Guidance literature:

With pyridine;

DOI:10.1021/jo00116a008

Reference yield:

benzoyl chloride (98-88-4) + (4R,5R,6S)-5,6-Bis-benzyloxy-4-benzyloxymethyl-cyclohex-2-enone (163563-91-5) → C35H34O5 + (1S,2R,3R,4R)-1-O-benzoyl-2,3-di-O-benzyl-4-benzyloxymethylcyclohex-5-ene-1,2,3-triol (151693-61-7)

Guidance literature:

(4R,5R,6S)-5,6-Bis-benzyloxy-4-benzyloxymethyl-cyclohex-2-enone; With sodium tetrahydroborate; cerium(III) chloride; In tetrahydrofuran; ethanol; at -78 ℃; for 0.166667h;

benzoyl chloride; In pyridine; at 20 ℃; for 16h; Further stages.;

DOI:10.1016/j.tetlet.2007.03.031

upstream raw materials:

benzoic acid

(1R,2R,3R,4R)-2,3-di-O-benzyl-4-benzyloxymethylcyclohex-5-ene-1,2,3-triol

benzoyl chloride

(1S,2R,3R,4R)-2,3-di-O-benzyl-4-benzyloxymethylcyclohex-5-ene-1,2,3-triol

Downstream raw materials:

(1S,2S,3R,4S)-2,3-di-O-benzyl-5-benzyloxymethyl-1-O-tert-butyldimethylsilylcyclohex-5-ene-1,2,3-triol

(1S,2R,3R,4R,5R,6R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-7-oxa-bicyclo[4.1.0]heptan-2-ol

(1R,2R,3R,4R,5R,6S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-7-oxa-bicyclo[4.1.0]heptan-2-ol

cyclophellitol