Methyl 3,4-O-Isopropylidene-2-O-(4-methoxybenzyl)-1-Thio-β-L-Fucopyranoside

Base Information

• Chemical Name: Methyl 3,4-O-Isopropylidene-2-O-(4-methoxybenzyl)-1-Thio-β-L-Fucopyranoside
• CAS No.: 130572-02-0
• Molecular Formula: C₁₈H₂₆O₅S
• Molecular Weight: 354.467

Synonyms:Methyl 3,4-O-Isopropylidene-2-O-(4-methoxybenzyl)-1-Thio-β-L-Fucopyranoside

Chemical Property of Methyl 3,4-O-Isopropylidene-2-O-(4-methoxybenzyl)-1-Thio-β-L-Fucopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of Methyl 3,4-O-Isopropylidene-2-O-(4-methoxybenzyl)-1-Thio-β-L-Fucopyranoside

There total 2 articles about Methyl 3,4-O-Isopropylidene-2-O-(4-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: 97.0%

methyl 3,4-O-isopropylidene-1-thio-β-L-fucopyranoside (130572-04-2) + p-methoxybenzyl chloride (824-94-2) → Methyl 3,4-O-Isopropylidene-2-O-(4-methoxybenzyl)-1-Thio-β-L-Fucopyranoside (130572-02-0)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 6h;

DOI:10.1055/s-1998-1994

Reference yield:

methyl 1-thio-β-L-fucopyranoside (114853-38-2) → Methyl 3,4-O-Isopropylidene-2-O-(4-methoxybenzyl)-1-Thio-β-L-Fucopyranoside (130572-02-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 96.8 percent / p-toluenesulfonic acid / dimethylformamide

2: NaH, DMF

With sodium hydride; toluene-4-sulfonic acid; N,N-dimethyl-formamide; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)97612-3

Reference yield: 95.0%

Methyl 3,4-O-Isopropylidene-2-O-(4-methoxybenzyl)-1-Thio-β-L-Fucopyranoside (130572-02-0) + 4-nitrophenyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside (142329-94-0) → 4-nitrophenyl O-<3,4-O-isopropylidene-2-O-(4-methoxybenzyl)-α-L-fucopyranosyl>-(1->3)-2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside (142329-79-1)

Guidance literature:

With 4 A molecular sieve; tetrabutylammomium bromide; copper(ll) bromide; In 1,2-dichloro-ethane; N,N-dimethyl-formamide; for 16h; Ambient temperature;

DOI:10.1016/S0008-6215(00)90562-7

upstream raw materials:

methyl 3,4-O-isopropylidene-1-thio-β-L-fucopyranoside

p-methoxybenzyl chloride

methyl 1-thio-β-L-fucopyranoside

Downstream raw materials:

Acetic acid (2S,3R,4R,5S,6R)-3-acetylamino-5-hydroxy-6-[(3aR,4S,6R,7S,7aR)-7-(4-methoxy-benzyloxy)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxymethyl]-2-(4-nitro-phenoxy)-tetrahydro-pyran-4-yl ester

C₃₆H₅₄O₁₄

C₄₂H₆₄O₁₈

4-nitrophenyl O-<3,4-O-isopropylidene-2-O-(4-methoxybenzyl)-α-L-fucopyranosyl>-(1->3)-2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

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