(2S,3R,4R,5S)-2,5-dibenzoyloxy-3,4-O-(1-methylethylidene)-3,4-hexanediol

Base Information

• Chemical Name: (2S,3R,4R,5S)-2,5-dibenzoyloxy-3,4-O-(1-methylethylidene)-3,4-hexanediol
• CAS No.: 159716-55-9
• Molecular Formula: C₂₃H₂₆O₆
• Molecular Weight: 398.456
• Mol file: 159716-55-9.mol

Synonyms:(2S,3R,4R,5S)-2,5-dibenzoyloxy-3,4-O-(1-methylethylidene)-3,4-hexanediol

Chemical Property of (2S,3R,4R,5S)-2,5-dibenzoyloxy-3,4-O-(1-methylethylidene)-3,4-hexanediol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R,5S)-2,5-dibenzoyloxy-3,4-O-(1-methylethylidene)-3,4-hexanediol

There total 1 articles about (2S,3R,4R,5S)-2,5-dibenzoyloxy-3,4-O-(1-methylethylidene)-3,4-hexanediol 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: 85.0%

benzoyl chloride (98-88-4) + (2S,3R,4R,5S)-3,4-O-(1-methylethylidene)-2,3,4,5-hexanetetraol (159716-52-6) → (2S,3R,4R,5S)-2,5-dibenzoyloxy-3,4-O-(1-methylethylidene)-3,4-hexanediol (159716-55-9)

Guidance literature:

With pyridine; at 0 ℃; for 1h;

DOI:10.1016/S0957-4166(00)86245-X

Reference yield: 74.0%

(2S,3R,4R,5S)-2,5-dibenzoyloxy-3,4-O-(1-methylethylidene)-3,4-hexanediol (159716-55-9) → C20H22O6 (159716-57-1)

Guidance literature:

With trifluoroacetic acid; at 0 ℃; for 1h;

DOI:10.1016/S0957-4166(00)86245-X

Reference yield:

(2S,3R,4R,5S)-2,5-dibenzoyloxy-3,4-O-(1-methylethylidene)-3,4-hexanediol (159716-55-9) → benzoic acid 1-methyl-2-oxo-ethyl ester (108552-81-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / 90percent aq. TFA / 1 h / 0 °C

2: 90 percent / Pb(OAc)4 / benzene / 1 h / Ambient temperature

With lead(IV) acetate; trifluoroacetic acid; In benzene;

DOI:10.1016/S0957-4166(00)86245-X

upstream raw materials:

benzoyl chloride

(2S,3R,4R,5S)-3,4-O-(1-methylethylidene)-2,3,4,5-hexanetetraol

Downstream raw materials:

C₂₀H₂₂O₆

benzoic acid 1-methyl-2-oxo-ethyl ester

Benzoic acid (E)-(S)-1-methyl-4-oxo-but-2-enyl ester

Benzoic acid (E)-(S)-4,4-dimethoxy-1-methyl-but-2-enyl ester