Methyl 2,3,6-Tri-O-benzyl-4-deoxy-4-C-(methylene)-α-D-xylo-hexopyranoside

Base Information

Chemical Name:Methyl 2,3,6-Tri-O-benzyl-4-deoxy-4-C-(methylene)-α-D-xylo-hexopyranoside
CAS No.:139070-96-5
Molecular Formula:C₂₉H₃₂O₅
Molecular Weight:460.57
Hs Code.:

Synonyms:Methyl 2,3,6-Tri-O-benzyl-4-deoxy-4-C-(methylene)-α-D-xylo-hexopyranoside

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Chemical Property of Methyl 2,3,6-Tri-O-benzyl-4-deoxy-4-C-(methylene)-α-D-xylo-hexopyranoside

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Technology Process of Methyl 2,3,6-Tri-O-benzyl-4-deoxy-4-C-(methylene)-α-D-xylo-hexopyranoside

There total 2 articles about Methyl 2,3,6-Tri-O-benzyl-4-deoxy-4-C-(methylene)-α-D-xylo-hexopyranoside 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: 79.0%

: 1779-49-3
Methyltriphenylphosphonium bromide

: 98807-61-5
1-O-methyl-2,3,6-tri-O-benzyl-4-keto-α-D-glucopyranoside

: 139070-96-5
Methyl 2,3,6-Tri-O-benzyl-4-deoxy-4-C-(methylene)-α-D-xylo-hexopyranoside

Guidance literature:: Methyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; hexane; at -60 ℃; for 1h; Inert atmosphere;

1-O-methyl-2,3,6-tri-O-benzyl-4-keto-α-D-glucopyranoside; In tetrahydrofuran; hexane; at -50 - 20 ℃;
DOI:10.1039/b917409e

Reference yield:

: 19488-48-3
methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside

: 139070-96-5
Methyl 2,3,6-Tri-O-benzyl-4-deoxy-4-C-(methylene)-α-D-xylo-hexopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 93 percent / DMSO; trifluoroacetic anhydride; Et₃N / CH₂Cl₂ / -78 - 20 °C

2: 71 percent / BuLi

With n-butyllithium; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In dichloromethane; 2: Wittig reaction;
DOI:10.1021/ol030081e

Reference yield: 35.0%

: 139070-96-5
Methyl 2,3,6-Tri-O-benzyl-4-deoxy-4-C-(methylene)-α-D-xylo-hexopyranoside

: 96026-75-4
Methyl 2,3,6-Tri-O-benzyl-4-C-(methyl)-α-D-glucopyranoside

: 127243-54-3
METHYL 2,3,6-TRI-O-BENZYL-4-DEOXY-4-HYDROXYMETHYL-α-D-GLUCO-PYRANOSIDE

: 127924-50-9
methyl 2,3,6-tri-O-benzyl-4-deoxy-4-C-(hydroxymethyl)-α-D-galactopyranoside

Guidance literature:: Methyl 2,3,6-Tri-O-benzyl-4-deoxy-4-C-(methylene)-α-D-xylo-hexopyranoside; With borane-THF; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

With dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; water; at 0 - 20 ℃; for 5h; Inert atmosphere;
DOI:10.1039/b917409e