(E,S,S)-methyl 4-O-benzyl-5,6-di-O-isopropylidene-4,5,6-trihydroxy-2-hexenoate

Base Information

• Chemical Name: (E,S,S)-methyl 4-O-benzyl-5,6-di-O-isopropylidene-4,5,6-trihydroxy-2-hexenoate
• CAS No.: 100906-48-7
• Molecular Formula: C₁₇H₂₂O₅
• Molecular Weight: 306.359
• Mol file: 100906-48-7.mol

Synonyms:(E,S,S)-methyl 4-O-benzyl-5,6-di-O-isopropylidene-4,5,6-trihydroxy-2-hexenoate

Chemical Property of (E,S,S)-methyl 4-O-benzyl-5,6-di-O-isopropylidene-4,5,6-trihydroxy-2-hexenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E,S,S)-methyl 4-O-benzyl-5,6-di-O-isopropylidene-4,5,6-trihydroxy-2-hexenoate

There total 12 articles about (E,S,S)-methyl 4-O-benzyl-5,6-di-O-isopropylidene-4,5,6-trihydroxy-2-hexenoate 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%

bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate (88738-78-7) + 2-O-benzyl-3,4-O-isopropylidene-L-threose (100906-42-1) → (Z,S,S)-methyl 4-O-benzyl-5,6-di-O-isopropylidene-4,5,6-trihydroxy-2-hexenoate (100906-43-2) + (E,S,S)-methyl 4-O-benzyl-5,6-di-O-isopropylidene-4,5,6-trihydroxy-2-hexenoate (100906-48-7)

Guidance literature:

With 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 0.5h;

DOI:10.1021/jo0521192

Reference yield: 6.0%

2-O-benzyl-3,4-O-isopropylidene-L-threose (100906-42-1) + methyl (triphenylphosphoranylidene)acetate (21204-67-1,2605-67-6) → (Z,S,S)-methyl 4-O-benzyl-5,6-di-O-isopropylidene-4,5,6-trihydroxy-2-hexenoate (100906-43-2) + (E,S,S)-methyl 4-O-benzyl-5,6-di-O-isopropylidene-4,5,6-trihydroxy-2-hexenoate (100906-48-7)

Guidance literature:

In methanol;

DOI:10.1016/S0040-4039(00)89235-7

Reference yield:

2-O-benzyl-L-threitol (84379-51-1,84379-52-2,124909-02-0,127000-44-6) → (E,S,S)-methyl 4-O-benzyl-5,6-di-O-isopropylidene-4,5,6-trihydroxy-2-hexenoate (100906-48-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / TsOH / 12 h / Ambient temperature

2: dimethyl sulfide, N-chlorosuccinimide / 1.) toluene, 6 h, 2.) toluene, from -25 deg C to RT

3: methanol / 20 h

With N-chloro-succinimide; dimethylsulfide; toluene-4-sulfonic acid; In methanol;

DOI:10.1016/0957-4166(96)00424-7

upstream raw materials:

2-O-benzyl-3,4-O-isopropylidene-L-threose

methyl (triphenylphosphoranylidene)acetate

bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate

benzyl bromide