S-ethyl 3,4-di-O-acetyl-2-O-p-methoxybenzyl-1-thio-β-L-fucopyranoside

Base Information

• Chemical Name: S-ethyl 3,4-di-O-acetyl-2-O-p-methoxybenzyl-1-thio-β-L-fucopyranoside
• CAS No.: 418764-37-1
• Molecular Formula: C₂₀H₂₈O₇S
• Molecular Weight: 412.504
• Mol file: 418764-37-1.mol

Synonyms:S-ethyl 3,4-di-O-acetyl-2-O-p-methoxybenzyl-1-thio-β-L-fucopyranoside

Chemical Property of S-ethyl 3,4-di-O-acetyl-2-O-p-methoxybenzyl-1-thio-β-L-fucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of S-ethyl 3,4-di-O-acetyl-2-O-p-methoxybenzyl-1-thio-β-L-fucopyranoside

There total 1 articles about S-ethyl 3,4-di-O-acetyl-2-O-p-methoxybenzyl-1-thio-β-L-fucopyranoside 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:

S-ethyl 3,4-O-isopropylidene-2-O-p-methoxybenzyl-1-thio-β-L-fucopyranoside (152015-42-4) → S-ethyl 3,4-di-O-acetyl-2-O-p-methoxybenzyl-1-thio-β-L-fucopyranoside (418764-37-1)

Guidance literature:

Multi-step reaction with 2 steps

1: CF₃CO₂H / CH₂Cl₂; H₂O / 2 h / -35 °C

2: 65 mg / 4-N,N-dimethylaminopyridine; pyridine / 48 h / 20 °C

With pyridine; dmap; trifluoroacetic acid; In dichloromethane; water;

DOI:10.1081/CAR-100108285

Reference yield: 83.0%

S-ethyl 3,4-di-O-acetyl-2-O-p-methoxybenzyl-1-thio-β-L-fucopyranoside (418764-37-1) + allyl 3,6-di-O-p-methoxybenzyl-4-O-methyl-β-D-galactopyranoside (418764-36-0) → allyl (3,4-di-O-acetyl-2-O-methyl-α-L-fucopyranosyl)-(1->2)-3,6-di-O-p-methoxybenzyl-4-O-methyl-β-D-galactopyranoside (418764-42-8) + allyl (3,4-di-O-acetyl-2-O-methyl-β-L-fucopyranosyl)-(1->2)-3,6-di-O-p-methoxybenzyl-4-O-methyl-β-D-galactopyranoside

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; In diethyl ether; dichloromethane; at 0 ℃; for 1h;

DOI:10.1081/CAR-100108285

Reference yield: 52.0%

methyl 2-acetylamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (87038-18-4) + S-ethyl 3,4-di-O-acetyl-2-O-p-methoxybenzyl-1-thio-β-L-fucopyranoside (418764-37-1) → methyl 2-acetamido-3-O-(3,4-di-O-acetyl-2-O-p-methoxylbenzyl-α-L-fucopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (1192700-42-7)

Guidance literature:

methyl 2-acetylamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside; S-ethyl 3,4-di-O-acetyl-2-O-p-methoxybenzyl-1-thio-β-L-fucopyranoside; In diethyl ether; at 20 ℃; for 1h; Inert atmosphere; Molecular sieve;

With methyl trifluoromethanesulfonate; In diethyl ether; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/jo901616p

upstream raw materials:

S-ethyl 3,4-O-isopropylidene-2-O-p-methoxybenzyl-1-thio-β-L-fucopyranoside

Downstream raw materials:

allyl (3,4-di-O-acetyl-2-O-methyl-α-L-fucopyranosyl)-(1->2)-3,6-di-O-p-methoxybenzyl-4-O-methyl-β-D-galactopyranoside

methyl 2-acetamido-3-O-(3,4-di-O-acetyl-2-O-p-methoxylbenzyl-α-L-fucopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside