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

Base Information

Chemical Name: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
CAS No.:273384-35-3
Molecular Formula:C₅₃H₆₀O₁₂
Molecular Weight:889.052
Hs Code.:

Synonyms: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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Chemical Property of 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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Technology Process of 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

There total 9 articles about 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 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: 71.0%

: 108-24-7
acetic anhydride

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

: 273384-35-3
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

Guidance literature:: With pyridine; at 0 ℃; for 2h;
DOI:10.1016/S0008-6215(99)00315-8

Reference yield:

: 100-39-0
benzyl bromide

: 273384-35-3
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

Guidance literature:: Multi-step reaction with 2 steps

1.1: dibutyltin oxide / benzene / 5 h / Heating

1.2: 93 percent / tetrabutylammonium bromide / 3 h / 50 °C

2.1: 71 percent / pyridine / 2 h / 0 °C

With pyridine; di(n-butyl)tin oxide; In benzene; 1.1: Metallation / 1.2: Etherification / 2.1: Acetylation;
DOI:10.1016/S0008-6215(99)00315-8

Reference yield:

: 113893-72-4
2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate

: 273384-35-3
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

Guidance literature:: Multi-step reaction with 7 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

7.1: 71 percent / pyridine / 2 h / 0 °C

With pyridine; 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 / 7.1: Acetylation;
DOI:10.1016/S0008-6215(99)00315-8