(2S)-methyl 2-trimethylsilyloxy-2-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate

Base Information

Chemical Name:(2S)-methyl 2-trimethylsilyloxy-2-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate
CAS No.:934349-41-4
Molecular Formula:C₄₀H₄₈O₈Si
Molecular Weight:684.902
Hs Code.:

Synonyms:(2S)-methyl 2-trimethylsilyloxy-2-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate

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Chemical Property of (2S)-methyl 2-trimethylsilyloxy-2-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate

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Technology Process of (2S)-methyl 2-trimethylsilyloxy-2-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate

There total 3 articles about (2S)-methyl 2-trimethylsilyloxy-2-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate 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: 72.0%

: 883143-12-2
(1R)-2,3,4,6-tetra-O-benzyl-3'(S)-carboxymethyl-spiro[1,5-anhydro-D-glucitol-1,2'-oxirane]

: 27607-77-8
trimethylsilyl trifluoromethanesulfonate

: 934349-42-5
(2S)-methyl 2-hydroxy-2-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate

: 934349-41-4
(2S)-methyl 2-trimethylsilyloxy-2-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate

Guidance literature:: With tri-n-butyl-tin hydride; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1016/j.carres.2008.04.018

Reference yield:

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 934349-41-4
(2S)-methyl 2-trimethylsilyloxy-2-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate

Guidance literature:: Multi-step reaction with 2 steps

1: 80 percent / LiHMDS / tetrahydrofuran / 2 h / -78 - 20 °C

2: tributyltin hydride / CH₂Cl₂ / 0.5 h / 0 °C

With tri-n-butyl-tin hydride; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;
DOI:10.1055/s-2007-968002

Reference yield:

: 4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9
2,3,4,6-Tetra-O-benzyl-D-glucopyranose

: 934349-41-4
(2S)-methyl 2-trimethylsilyloxy-2-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: pyridinium chlorochromate / dichloromethane

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C

2.2: 1.42 h / 20 °C

3.1: tri-n-butyl-tin hydride / dichloromethane / 0.5 h / 0 °C

With tri-n-butyl-tin hydride; pyridinium chlorochromate; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;