allyl 2',3'-di-O-benzyl-6'-O-p-methoxybenzyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Base Information

• Chemical Name: allyl 2',3'-di-O-benzyl-6'-O-p-methoxybenzyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• CAS No.: 1385047-51-7
• Molecular Formula: C₅₈H₆₄O₁₂
• Molecular Weight: 953.139

Synonyms:allyl 2',3'-di-O-benzyl-6'-O-p-methoxybenzyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Chemical Property of allyl 2',3'-di-O-benzyl-6'-O-p-methoxybenzyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Chemical Property:

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Technology Process of allyl 2',3'-di-O-benzyl-6'-O-p-methoxybenzyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

There total 7 articles about allyl 2',3'-di-O-benzyl-6'-O-p-methoxybenzyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 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: 71.4%

allyl 2',3'-di-O-benzyl-4',6'-O-p-methoxybenzilidene-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (1385047-48-2) → allyl 2',3'-di-O-benzyl-6'-O-p-methoxybenzyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (1385047-51-7)

Guidance literature:

allyl 2',3'-di-O-benzyl-4',6'-O-p-methoxybenzilidene-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside; With sodium cyanoborohydride; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

With trifluoroacetic acid; In N,N-dimethyl-formamide; at 0 ℃; Molecular sieve; Inert atmosphere;

DOI:10.1039/c2cc30805c

Reference yield:

2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranose (18464-08-9,66073-13-0,71623-44-4,101981-29-7,109922-72-7,109922-73-8,132287-75-3,132287-76-4,132287-78-6,132303-63-0,134311-82-3,134333-39-4) → allyl 2',3'-di-O-benzyl-6'-O-p-methoxybenzyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (1385047-51-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 3 h / 20 °C

2.1: boron trifluoride diethyl etherate / dichloromethane / -78 - 20 °C / Molecular sieve

3.1: sodium methylate / methanol; dichloromethane / 0 - 20 °C

4.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 4 h / 40 °C / 30 Torr

5.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C

5.2: 5 h / 0 °C / Reflux

6.1: sodium cyanoborohydride / N,N-dimethyl-formamide / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere

6.2: 0 °C / Molecular sieve; Inert atmosphere

With boron trifluoride diethyl etherate; sodium methylate; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; mineral oil;

DOI:10.1039/c2cc30805c

Reference yield:

4-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl trichloracetimidate (92052-38-5,106256-81-9,106256-89-7,126736-02-5,132287-70-8,132287-71-9,139403-73-9,130703-21-8) → allyl 2',3'-di-O-benzyl-6'-O-p-methoxybenzyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (1385047-51-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: boron trifluoride diethyl etherate / dichloromethane / -78 - 20 °C / Molecular sieve

2.1: sodium methylate / methanol; dichloromethane / 0 - 20 °C

3.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 4 h / 40 °C / 30 Torr

4.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C

4.2: 5 h / 0 °C / Reflux

5.1: sodium cyanoborohydride / N,N-dimethyl-formamide / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere

5.2: 0 °C / Molecular sieve; Inert atmosphere

With boron trifluoride diethyl etherate; sodium methylate; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; mineral oil;

DOI:10.1039/c2cc30805c

upstream raw materials:

2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranose

allyl 4',6'-O-p-methoxybenzylidene-β-D-glucopyranosyl-(1->4)-β-D-glucopyranoside

allyl 2',3'-di-O-benzyl-4',6'-O-p-methoxybenzilidene-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

allyl 2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside

Downstream raw materials:

2',3'-di-O-benzyl-6'-O-p-methoxybenzyl-4'-O-methyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranose

2',3'-di-O-benzyl-6'-O-p-methoxybenzyl-4'-O-methyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α,β-D-glucopyranosyl trichloroacetoimidate

allyl 2',3'-di-O-benzyl-6'-O-p-methoxybenzyl-4'-O-methyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

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