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

Base Information

• Chemical Name: (2S)-methyl 2-hydroxy-2-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate
• CAS No.: 934349-42-5
• Molecular Formula: C₃₇H₄₀O₈
• Molecular Weight: 612.72
• Mol file: 934349-42-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about (2S)-methyl 2-hydroxy-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: 100.0%

(1R)-2,3,4,6-tetra-O-benzyl-3'(S)-carboxymethyl-spiro[1,5-anhydro-D-glucitol-1,2'-oxirane] (883143-12-2) → (2S)-methyl 2-hydroxy-2-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate (934349-42-5)

Guidance literature:

(1R)-2,3,4,6-tetra-O-benzyl-3'(S)-carboxymethyl-spiro[1,5-anhydro-D-glucitol-1,2'-oxirane]; With trimethylsilyl trifluoromethanesulfonate; tri-n-butyl-tin hydride; In dichloromethane; at 0 ℃; for 0.5h;

With trifluoroacetic acid; In tetrahydrofuran; dichloromethane; for 2h;

DOI:10.1055/s-2007-968002

Reference yield: 100.0%

(2S)-methyl 2-trimethylsilyloxy-2-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate (934349-41-4) → (2S)-methyl 2-hydroxy-2-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate (934349-42-5)

Guidance literature:

With water; trifluoroacetic acid; In tetrahydrofuran; Product distribution / selectivity;

Reference yield: 72.0%

(1R)-2,3,4,6-tetra-O-benzyl-3'(S)-carboxymethyl-spiro[1,5-anhydro-D-glucitol-1,2'-oxirane] (883143-12-2) + trimethylsilyl trifluoromethanesulfonate (27607-77-8) → (2S)-methyl 2-hydroxy-2-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate (934349-42-5) + (2S)-methyl 2-trimethylsilyloxy-2-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate (934349-41-4)

Guidance literature:

With tri-n-butyl-tin hydride; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1016/j.carres.2008.04.018

upstream raw materials:

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

trimethylsilyl trifluoromethanesulfonate

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

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

Downstream raw materials:

C₅₁H₅₉N₅O₁₂

C₄₁H₅₇N₅O₁₂

C₄₁H₅₆N₄O₁₃

benzylamino-(3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid methyl ester