methyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->4)-2-O-acetyl-3-O-allyl-6-O-benzyl-α-D-mannopyranosyl-(1->4)-[2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranosid]uronate

Base Information

Chemical Name:methyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->4)-2-O-acetyl-3-O-allyl-6-O-benzyl-α-D-mannopyranosyl-(1->4)-[2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranosid]uronate
CAS No.:569650-74-4
Molecular Formula:C₇₁H₈₆O₁₇Si
Molecular Weight:1239.54
Hs Code.:

methyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->4)-2-O-acetyl-3-O-allyl-6-O-benzyl-α-D-mannopyranosyl-(1->4)-[2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranosid]uronate

Synonyms:methyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->4)-2-O-acetyl-3-O-allyl-6-O-benzyl-α-D-mannopyranosyl-(1->4)-[2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranosid]uronate

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Chemical Property of methyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->4)-2-O-acetyl-3-O-allyl-6-O-benzyl-α-D-mannopyranosyl-(1->4)-[2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranosid]uronate

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Technology Process of methyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->4)-2-O-acetyl-3-O-allyl-6-O-benzyl-α-D-mannopyranosyl-(1->4)-[2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranosid]uronate

There total 12 articles about methyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->4)-2-O-acetyl-3-O-allyl-6-O-benzyl-α-D-mannopyranosyl-(1->4)-[2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranosid]uronate 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: 63.0%

: 186581-53-3,908094-01-9,334-88-3
diazomethane

: 569650-73-3
acetic acid 4-allyloxy-6-benzyloxymethyl-2-[4,5-bis-benzyloxy-2-hydroxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yloxy]-5-(3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

: 569650-74-4
methyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->4)-2-O-acetyl-3-O-allyl-6-O-benzyl-α-D-mannopyranosyl-(1->4)-[2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranosid]uronate

Guidance literature:: acetic acid 4-allyloxy-6-benzyloxymethyl-2-[4,5-bis-benzyloxy-2-hydroxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yloxy]-5-(3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester; With chromium(VI) oxide; sulfuric acid; In dichloromethane; acetone; at 0 - 20 ℃; for 9.25h;

diazomethane; In diethyl ether; dichloromethane;
DOI:10.1016/S0008-6215(02)00499-8

Reference yield:

: 116514-50-2,128962-63-0,131545-02-3,136758-06-0,99409-34-4,116391-11-8
ethyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside

: 569650-74-4
methyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->4)-2-O-acetyl-3-O-allyl-6-O-benzyl-α-D-mannopyranosyl-(1->4)-[2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranosid]uronate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 74 percent / N-iodosuccinimide; TfOH / CH₂Cl₂ / 0.75 h / -10 °C

2.1: 70 percent / N-iodosuccinimide; TfOH / CH₂Cl₂ / 0.75 h / -10 °C

3.1: 80 percent / aq. AcOH / 4 h / 80 °C

4.1: CrO₃; aq. H₂SO₄ / acetone; CH₂Cl₂ / 9.25 h / 0 - 20 °C

4.2: 63 percent / CH₂Cl₂; diethyl ether

With chromium(VI) oxide; N-iodo-succinimide; trifluorormethanesulfonic acid; sulfuric acid; acetic acid; In dichloromethane; acetone;
DOI:10.1016/S0008-6215(02)00499-8

Reference yield:

: 100-39-0
benzyl bromide

: 569650-74-4
methyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->4)-2-O-acetyl-3-O-allyl-6-O-benzyl-α-D-mannopyranosyl-(1->4)-[2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranosid]uronate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 90 percent / NaH / dimethylformamide / 6 h / 20 °C

2.1: 79 percent / NaCNBH₃; TFA / dimethylformamide / 7 h / 20 °C

3.1: 70 percent / N-iodosuccinimide; TfOH / CH₂Cl₂ / 0.75 h / -10 °C

4.1: 80 percent / aq. AcOH / 4 h / 80 °C

5.1: CrO₃; aq. H₂SO₄ / acetone; CH₂Cl₂ / 9.25 h / 0 - 20 °C

5.2: 63 percent / CH₂Cl₂; diethyl ether

With chromium(VI) oxide; N-iodo-succinimide; trifluorormethanesulfonic acid; sulfuric acid; sodium hydride; sodium cyanoborohydride; acetic acid; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0008-6215(02)00499-8