methyl 2-oxo-2-(1-allyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate

Base Information

Chemical Name:methyl 2-oxo-2-(1-allyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate
CAS No.:883143-17-7
Molecular Formula:C₄₀H₄₂O₈
Molecular Weight:650.769
Hs Code.:

Synonyms:methyl 2-oxo-2-(1-allyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate

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Chemical Property of methyl 2-oxo-2-(1-allyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate

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Technology Process of methyl 2-oxo-2-(1-allyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate

There total 4 articles about methyl 2-oxo-2-(1-allyl-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: 97.0%

: 1152330-47-6
methyl (2S)-hydroxy-2-(1-allyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate

: 883143-17-7
methyl 2-oxo-2-(1-allyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate

Guidance literature:: methyl (2S)-hydroxy-2-(1-allyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate; With dimethyl sulfoxide; trifluoroacetic anhydride; In dichloromethane; at -65 ℃; for 0.916667h; Inert atmosphere;

With triethylamine; In dichloromethane; at -65 - 20 ℃; Inert atmosphere;
DOI:10.1016/j.carres.2008.12.024

Reference yield: 80.0%

: 883143-14-4
((2S,3R,4S,5R,6R)-2-Allyl-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-hydroxy-acetic acid methyl ester

: 883143-17-7
methyl 2-oxo-2-(1-allyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate

: 883143-18-8
((2S,3R,4S,5R,6R)-2-Allyl-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-oxo-acetic acid methyl ester

Guidance literature:: With dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In dichloromethane; at -78 ℃; for 2h;
DOI:10.1055/s-2005-922768

Reference yield:

: 883143-13-3
((2R,3R,4S,5R,6R)-2-Allyl-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-trimethylsilanyloxy-acetic acid methyl ester

: 883143-17-7
methyl 2-oxo-2-(1-allyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / aq. TFA / tetrahydrofuran / 20 °C

2: 80 percent / DMSO; trifluoroacetic anhydride; Et₃N / CH₂Cl₂ / 2 h / -78 °C

With dimethyl sulfoxide; triethylamine; trifluoroacetic acid; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane;
DOI:10.1055/s-2005-922768