Acetic acid (2S,3R,4S,5S)-1-(1-benzenesulfonyl-2-methyl-propyl)-2,3,4-tris-benzyloxy-5-methoxy-6-(4-methoxy-benzyloxy)-hexyl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4S,5S)-1-(1-benzenesulfonyl-2-methyl-propyl)-2,3,4-tris-benzyloxy-5-methoxy-6-(4-methoxy-benzyloxy)-hexyl ester
• CAS No.: 136289-19-5
• Molecular Formula: C₄₈H₅₆O₁₀S
• Molecular Weight: 825.033
• Mol file: 136289-19-5.mol

Synonyms:Acetic acid (2S,3R,4S,5S)-1-(1-benzenesulfonyl-2-methyl-propyl)-2,3,4-tris-benzyloxy-5-methoxy-6-(4-methoxy-benzyloxy)-hexyl ester

Chemical Property of Acetic acid (2S,3R,4S,5S)-1-(1-benzenesulfonyl-2-methyl-propyl)-2,3,4-tris-benzyloxy-5-methoxy-6-(4-methoxy-benzyloxy)-hexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2S,3R,4S,5S)-1-(1-benzenesulfonyl-2-methyl-propyl)-2,3,4-tris-benzyloxy-5-methoxy-6-(4-methoxy-benzyloxy)-hexyl ester

There total 2 articles about Acetic acid (2S,3R,4S,5S)-1-(1-benzenesulfonyl-2-methyl-propyl)-2,3,4-tris-benzyloxy-5-methoxy-6-(4-methoxy-benzyloxy)-hexyl ester 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:

(2R,3R,4S,5S,6S)-3,4,5-Tris-benzyloxy-6-methoxy-7-(4-methoxy-benzyloxy)-heptane-1,2-diol → Acetic acid (2S,3R,4S,5S)-1-(1-benzenesulfonyl-2-methyl-propyl)-2,3,4-tris-benzyloxy-5-methoxy-6-(4-methoxy-benzyloxy)-hexyl ester (136289-19-5)

Guidance literature:

Multi-step reaction with 2 steps

1: NaIO₄ / ethanol / 1 h / Ambient temperature

2: 1) n-BuLi, 2) pyridine, DMAP / THF, -30 deg C, 1 h, 2) RT, 3 h

With pyridine; dmap; sodium periodate; n-butyllithium; In ethanol;

DOI:10.1016/S0040-4039(00)92722-9

Reference yield:

isobutyl phenyl sulfone (34009-07-9) + acetic anhydride (108-24-7) + (2S,3R,4S,5S)-2,3,4-Tris-benzyloxy-5-methoxy-6-(4-methoxy-benzyloxy)-hexanal → Acetic acid (2S,3R,4S,5S)-1-(1-benzenesulfonyl-2-methyl-propyl)-2,3,4-tris-benzyloxy-5-methoxy-6-(4-methoxy-benzyloxy)-hexyl ester (136289-19-5)

Guidance literature:

With pyridine; dmap; n-butyllithium; Multistep reaction; THF, -30 deg C, 1 h, 2) RT, 3 h;

DOI:10.1016/S0040-4039(00)92722-9

Reference yield: 50.0%

Acetic acid (2S,3R,4S,5S)-1-(1-benzenesulfonyl-2-methyl-propyl)-2,3,4-tris-benzyloxy-5-methoxy-6-(4-methoxy-benzyloxy)-hexyl ester (136289-19-5) → 1-Methoxy-4-((E)-(2S,3S,4S,5R)-3,4,5-tris-benzyloxy-2-methoxy-8-methyl-non-6-enyloxymethyl)-benzene (136289-20-8)

Guidance literature:

With disodium hydrogenphosphate; sodium amalgam; In methanol; at 0 ℃; for 2h;

DOI:10.1016/S0040-4039(00)92722-9

upstream raw materials:

isobutyl phenyl sulfone

acetic anhydride

Downstream raw materials:

1-Methoxy-4-((E)-(2S,3S,4S,5R)-3,4,5-tris-benzyloxy-2-methoxy-8-methyl-non-6-enyloxymethyl)-benzene

(E)-(2S,3S,4S,5R)-3,4,5-Tris-benzyloxy-2-methoxy-8-methyl-non-6-en-1-ol

(E)-(2R,3R,4S,5R)-3,4,5-Tris-benzyloxy-2-methoxy-8-methyl-non-6-enoic acid methyl ester