methyl [2,3,6-tri-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glucopyranosyl]-(1→4)-1,2-di-O-acetyl-3-O-methyl-α-L-idopyranosyluronate

Base Information

Chemical Name:methyl [2,3,6-tri-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glucopyranosyl]-(1→4)-1,2-di-O-acetyl-3-O-methyl-α-L-idopyranosyluronate
CAS No.:1428238-22-5
Molecular Formula:C₄₇H₅₄O₁₅
Molecular Weight:858.937
Hs Code.:

Synonyms:methyl [2,3,6-tri-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glucopyranosyl]-(1→4)-1,2-di-O-acetyl-3-O-methyl-α-L-idopyranosyluronate

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Chemical Property of methyl [2,3,6-tri-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glucopyranosyl]-(1→4)-1,2-di-O-acetyl-3-O-methyl-α-L-idopyranosyluronate

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Technology Process of methyl [2,3,6-tri-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glucopyranosyl]-(1→4)-1,2-di-O-acetyl-3-O-methyl-α-L-idopyranosyluronate

There total 3 articles about methyl [2,3,6-tri-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glucopyranosyl]-(1→4)-1,2-di-O-acetyl-3-O-methyl-α-L-idopyranosyluronate 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:

: 1402422-10-9
methyl (1,2-di-O-acetyl-3-O-methyl-β-L-idopyranose)uronate

: 1428238-20-3
phenyl 2,3,6,-tri-O-benzyl-4-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside

: 1428238-21-4
methyl [2,3,6-tri-O-benzyl-4-O-(4-methoxybenzyl)-α-D-glucopyranosyl]-(1→4)-1,2-di-O-acetyl-3-O-methyl-β-L-idopyranosyluronate

: 1428238-22-5
methyl [2,3,6-tri-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glucopyranosyl]-(1→4)-1,2-di-O-acetyl-3-O-methyl-α-L-idopyranosyluronate

Guidance literature:: methyl (1,2-di-O-acetyl-3-O-methyl-β-L-idopyranose)uronate; phenyl 2,3,6,-tri-O-benzyl-4-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside; In dichloromethane; at -45 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

With N-iodo-succinimide; trifluorormethanesulfonic acid; In tetrahydrofuran; dichloromethane; at -45 - -10 ℃; for 2h; Overall yield = 68 %; Overall yield = 1.3 g; Molecular sieve; Inert atmosphere;
DOI:10.1016/j.tet.2013.02.076

Reference yield:

: phenyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside

: 1428238-21-4
methyl [2,3,6-tri-O-benzyl-4-O-(4-methoxybenzyl)-α-D-glucopyranosyl]-(1→4)-1,2-di-O-acetyl-3-O-methyl-β-L-idopyranosyluronate

: 1428238-22-5
methyl [2,3,6-tri-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glucopyranosyl]-(1→4)-1,2-di-O-acetyl-3-O-methyl-α-L-idopyranosyluronate

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C

1.2: 4 h / 20 °C

2.1: dichloromethane / 0.5 h / -45 °C / Molecular sieve; Inert atmosphere

2.2: 2 h / -45 - -10 °C / Molecular sieve; Inert atmosphere

With sodium hydride; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2013.02.076

Reference yield:

: 1428238-38-3
phenyl 2,3-di-O-benzyl-4,6-O-(4-methoxy)benzylidene-1-thio-β-D-glucopyranoside

: 1428238-21-4
methyl [2,3,6-tri-O-benzyl-4-O-(4-methoxybenzyl)-α-D-glucopyranosyl]-(1→4)-1,2-di-O-acetyl-3-O-methyl-β-L-idopyranosyluronate

: 1428238-22-5
methyl [2,3,6-tri-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glucopyranosyl]-(1→4)-1,2-di-O-acetyl-3-O-methyl-α-L-idopyranosyluronate

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium aluminium tetrahydride; aluminum (III) chloride / dichloromethane; diethyl ether / 0.5 h / 0 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C

2.2: 4 h / 20 °C

3.1: dichloromethane / 0.5 h / -45 °C / Molecular sieve; Inert atmosphere

3.2: 2 h / -45 - -10 °C / Molecular sieve; Inert atmosphere

With aluminum (III) chloride; lithium aluminium tetrahydride; sodium hydride; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2013.02.076