(2S,3R,4E)-1-(4-O-(4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranosyl)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyloxy)-3-benzyloxy-2-hexacosanoylamidooctadec-4-ene

Base Information

• Chemical Name: (2S,3R,4E)-1-(4-O-(4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranosyl)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyloxy)-3-benzyloxy-2-hexacosanoylamidooctadec-4-ene
• CAS No.: 1597422-19-9
• Molecular Formula: C₁₀₀H₁₃₅NO₁₉
• Molecular Weight: 1655.17
• Mol file: 1597422-19-9.mol

Synonyms:(2S,3R,4E)-1-(4-O-(4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranosyl)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyloxy)-3-benzyloxy-2-hexacosanoylamidooctadec-4-ene

Chemical Property of (2S,3R,4E)-1-(4-O-(4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranosyl)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyloxy)-3-benzyloxy-2-hexacosanoylamidooctadec-4-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4E)-1-(4-O-(4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranosyl)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyloxy)-3-benzyloxy-2-hexacosanoylamidooctadec-4-ene

There total 1 articles about (2S,3R,4E)-1-(4-O-(4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranosyl)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyloxy)-3-benzyloxy-2-hexacosanoylamidooctadec-4-ene 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%

Trimethyl orthoacetate (1445-45-0) + (2S,3R,4E)-1-(4-O-(2,6-di-O-benzoyl-β-D-galactopyranosyl)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyloxy)-3-benzyloxy-2-hexacosanoylamidooctadec-4-ene (1597422-18-8) → (2S,3R,4E)-1-(4-O-(4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranosyl)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyloxy)-3-benzyloxy-2-hexacosanoylamidooctadec-4-ene (1597422-19-9)

Guidance literature:

With camphor-10-sulfonic acid; In dichloromethane; at 20 ℃; for 16h; regioselective reaction; Inert atmosphere;

DOI:10.1039/c4ob00241e

Reference yield: 69.0%

O-(2,3,4-tri-O-benzyl-6-deoxy-α-D-galactopyranosyl) trichloroacetimidate (1597422-16-6) + (2S,3R,4E)-1-(4-O-(4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranosyl)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyloxy)-3-benzyloxy-2-hexacosanoylamidooctadec-4-ene (1597422-19-9) → (2S,3R,4E)-1-(4-O-(4-O-acetyl-2,6-di-O-benzoyl-3-O-(2,3,4-tri-O-benzyl-6-deoxy-α-D-galactopyranosyl)-β-D-galactopyranosyl)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyloxy)-3-benzyloxy-2-hexacosanoylamidooctadec-4-ene (1597422-21-3)

Guidance literature:

O-(2,3,4-tri-O-benzyl-6-deoxy-α-D-galactopyranosyl) trichloroacetimidate; (2S,3R,4E)-1-(4-O-(4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranosyl)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyloxy)-3-benzyloxy-2-hexacosanoylamidooctadec-4-ene; In dichloromethane; for 3h; Molecular sieve; Inert atmosphere;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -40 - 20 ℃; for 21h; Inert atmosphere; Molecular sieve;

DOI:10.1039/c4ob00241e

Reference yield: 43.0%

(2S,3R,4E)-1-(4-O-(4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranosyl)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyloxy)-3-benzyloxy-2-hexacosanoylamidooctadec-4-ene (1597422-19-9) + 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl trichloroacetimidate (150969-30-5) → (2S,3R,4E)-1-(4-O-(4-O-acetyl-2,6-di-O-benzoyl-3-O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-β-D-galactopyranosyl)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyloxy)-3-benzyloxy-2-hexacosanoylamidooctadec-4-ene

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 - 20 ℃; Molecular sieve; Inert atmosphere;

DOI:10.1039/c4ob00241e

upstream raw materials:

Trimethyl orthoacetate

(2S,3R,4E)-1-(4-O-(2,6-di-O-benzoyl-β-D-galactopyranosyl)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyloxy)-3-benzyloxy-2-hexacosanoylamidooctadec-4-ene

Downstream raw materials:

(2S,3R,4E)-1-(4-O-(4-O-acetyl-2,6-di-O-benzoyl-3-O-(2,3,4-tri-O-benzyl-6-deoxy-α-D-galactopyranosyl)-β-D-galactopyranosyl)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyloxy)-3-benzyloxy-2-hexacosanoylamidooctadec-4-ene