methyl 2,3,6-tri-O-benzyl-4-O-(2,3,6-tri-O-methyl-5-C-vinyl-β-D-glucopyranosyl)-α-D-glucopyranoside

Base Information

Chemical Name:methyl 2,3,6-tri-O-benzyl-4-O-(2,3,6-tri-O-methyl-5-C-vinyl-β-D-glucopyranosyl)-α-D-glucopyranoside
CAS No.:403725-21-3
Molecular Formula:C₃₉H₅₀O₁₁
Molecular Weight:694.819
Hs Code.:

Synonyms:methyl 2,3,6-tri-O-benzyl-4-O-(2,3,6-tri-O-methyl-5-C-vinyl-β-D-glucopyranosyl)-α-D-glucopyranoside

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Chemical Property of methyl 2,3,6-tri-O-benzyl-4-O-(2,3,6-tri-O-methyl-5-C-vinyl-β-D-glucopyranosyl)-α-D-glucopyranoside

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Technology Process of methyl 2,3,6-tri-O-benzyl-4-O-(2,3,6-tri-O-methyl-5-C-vinyl-β-D-glucopyranosyl)-α-D-glucopyranoside

There total 7 articles about methyl 2,3,6-tri-O-benzyl-4-O-(2,3,6-tri-O-methyl-5-C-vinyl-β-D-glucopyranosyl)-α-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: 65.0%

: 403725-12-2
methyl 2,3,6-tri-O-benzyl-4-O-(2,3-di-O-methyl-5-C-vinyl-β-D-glucopyranosyl)-α-D-glucopyranoside

: 74-88-4
methyl iodide

: 403725-21-3
methyl 2,3,6-tri-O-benzyl-4-O-(2,3,6-tri-O-methyl-5-C-vinyl-β-D-glucopyranosyl)-α-D-glucopyranoside

Guidance literature:: methyl 2,3,6-tri-O-benzyl-4-O-(2,3-di-O-methyl-5-C-vinyl-β-D-glucopyranosyl)-α-D-glucopyranoside; With di(n-butyl)tin oxide; In toluene; for 3h; Heating;

methyl iodide; In N,N-dimethyl-formamide; at 50 ℃; for 6h;
DOI:10.1002/1521-3765(20011119)7:22<4821::AID-CHEM4821>3.0.CO;2-N

Reference yield:

: 202648-84-8
1,2,4,6-tetra-O-acetyl-3-O-methyl-5-C-vinyl-β-D-gluco-pyranose

: 403725-21-3
methyl 2,3,6-tri-O-benzyl-4-O-(2,3,6-tri-O-methyl-5-C-vinyl-β-D-glucopyranosyl)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: 85 percent / TMSOTf; molecular sieves / CH₂Cl₂ / 2 h / -78 - 20 °C

2.1: Na; MeOH / 3 h / 20 °C

3.1: 1.7 g / p-TsOH / acetone / 16 h / 20 °C

4.1: NaH / tetrahydrofuran / 1 h / 20 °C

5.1: 1.16 g / aq. AcOH / 3 h / 70 °C

6.1: Bu₂SnO / toluene / 3 h / Heating

6.2: 65 percent / dimethylformamide / 6 h / 50 °C

With methanol; molecular sieve; trimethylsilyl trifluoromethanesulfonate; sodium; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; acetic acid; In tetrahydrofuran; dichloromethane; acetone; toluene;
DOI:10.1002/1521-3765(20011119)7:22<4821::AID-CHEM4821>3.0.CO;2-N

Reference yield:

: 202649-52-3
methyl 2,3,6-tri-O-benzyl-4-O-(4,6-O-isopropylidene-3-O-methyl-5-C-vinyl-β-D-glucopyranosyl)-α-D-glucopyranoside

: 403725-21-3
methyl 2,3,6-tri-O-benzyl-4-O-(2,3,6-tri-O-methyl-5-C-vinyl-β-D-glucopyranosyl)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaH / tetrahydrofuran / 1 h / 20 °C

2.1: 1.16 g / aq. AcOH / 3 h / 70 °C

3.1: Bu₂SnO / toluene / 3 h / Heating

3.2: 65 percent / dimethylformamide / 6 h / 50 °C

With sodium hydride; di(n-butyl)tin oxide; acetic acid; In tetrahydrofuran; toluene;
DOI:10.1002/1521-3765(20011119)7:22<4821::AID-CHEM4821>3.0.CO;2-N