allyl 3-O-benzyl-4-O-(p-methoxybenzyl)-α-L-rhamnopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside

Base Information

• Chemical Name: allyl 3-O-benzyl-4-O-(p-methoxybenzyl)-α-L-rhamnopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside
• CAS No.: 273384-33-1
• Molecular Formula: C₅₁H₅₈O₁₁
• Molecular Weight: 847.015

Synonyms:allyl 3-O-benzyl-4-O-(p-methoxybenzyl)-α-L-rhamnopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside

Chemical Property of allyl 3-O-benzyl-4-O-(p-methoxybenzyl)-α-L-rhamnopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of allyl 3-O-benzyl-4-O-(p-methoxybenzyl)-α-L-rhamnopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside

There total 7 articles about allyl 3-O-benzyl-4-O-(p-methoxybenzyl)-α-L-rhamnopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside 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: 93.0%

benzyl bromide (100-39-0) + allyl 4-O-(p-methoxybenzyl)-α-L-rhamnopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside (273384-31-9) → allyl 3-O-benzyl-4-O-(p-methoxybenzyl)-α-L-rhamnopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside (273384-33-1)

Guidance literature:

allyl 4-O-(p-methoxybenzyl)-α-L-rhamnopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside; With di(n-butyl)tin oxide; In benzene; for 5h; Heating;

benzyl bromide; With tetrabutylammomium bromide; at 50 ℃; for 3h;

DOI:10.1016/S0008-6215(99)00315-8

Reference yield:

2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate (113893-72-4) → allyl 3-O-benzyl-4-O-(p-methoxybenzyl)-α-L-rhamnopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside (273384-33-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 97 percent / 4 Angstroem mol. sieves; silver triflate / CH₂Cl₂ / 24 h / 20 °C

2.1: 70 percent / NaOMe / methanol / 24 h / 20 °C

3.1: 93 percent / p-TsOH / 24 h / 20 °C

4.1: 65 percent / NaH / dimethylformamide; light petroleum / 20 °C

5.1: 67 percent / 80 percent aq. AcOH / 2.5 h / 50 °C

6.1: dibutyltin oxide / benzene / 5 h / Heating

6.2: 93 percent / tetrabutylammonium bromide / 3 h / 50 °C

With 4 A molecular sieve; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; acetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; Petroleum ether; benzene; 1.1: Etherification / 2.1: Deacetylation / 3.1: Etherification / 4.1: Etherification / 5.1: Hydrolysis / 6.1: Metallation / 6.2: Etherification;

DOI:10.1016/S0008-6215(99)00315-8

Reference yield:

allyl 2,3,6-tri-O-benzyl-β-D-galactopyranoside (150969-29-2) → allyl 3-O-benzyl-4-O-(p-methoxybenzyl)-α-L-rhamnopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside (273384-33-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 97 percent / 4 Angstroem mol. sieves; silver triflate / CH₂Cl₂ / 24 h / 20 °C

2.1: 70 percent / NaOMe / methanol / 24 h / 20 °C

3.1: 93 percent / p-TsOH / 24 h / 20 °C

4.1: 65 percent / NaH / dimethylformamide; light petroleum / 20 °C

5.1: 67 percent / 80 percent aq. AcOH / 2.5 h / 50 °C

6.1: dibutyltin oxide / benzene / 5 h / Heating

6.2: 93 percent / tetrabutylammonium bromide / 3 h / 50 °C

With 4 A molecular sieve; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; acetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; Petroleum ether; benzene; 1.1: Etherification / 2.1: Deacetylation / 3.1: Etherification / 4.1: Etherification / 5.1: Hydrolysis / 6.1: Metallation / 6.2: Etherification;

DOI:10.1016/S0008-6215(99)00315-8

upstream raw materials:

benzyl bromide

allyl 4-O-(p-methoxybenzyl)-α-L-rhamnopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside

2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate

allyl 2,3,6-tri-O-benzyl-β-D-galactopyranoside

Downstream raw materials:

allyl 2-O-acetyl-3-O-benzyl-4-O-(p-methoxybenzyl)-α-L-rhamnopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside

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