(6S)-methyl 6-C-allyl-4-O-benzyl-2,3,6-tri-O-methyl-α-D-galactopyranoside

Base Information

Chemical Name:(6S)-methyl 6-C-allyl-4-O-benzyl-2,3,6-tri-O-methyl-α-D-galactopyranoside
CAS No.:1454689-59-8
Molecular Formula:C₂₀H₃₀O₆
Molecular Weight:366.455
Hs Code.:

Synonyms:(6S)-methyl 6-C-allyl-4-O-benzyl-2,3,6-tri-O-methyl-α-D-galactopyranoside

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (6S)-methyl 6-C-allyl-4-O-benzyl-2,3,6-tri-O-methyl-α-D-galactopyranoside

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Technology Process of (6S)-methyl 6-C-allyl-4-O-benzyl-2,3,6-tri-O-methyl-α-D-galactopyranoside

There total 5 articles about (6S)-methyl 6-C-allyl-4-O-benzyl-2,3,6-tri-O-methyl-α-D-galactopyranoside 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: 87.0%

: 1454689-57-6
(6S)-methyl 6-C-allyl-4-O-benzyl-2,3-di-O-methyl-α-D-galactopyranoside

: 74-88-4
methyl iodide

: 1454689-59-8
(6S)-methyl 6-C-allyl-4-O-benzyl-2,3,6-tri-O-methyl-α-D-galactopyranoside

Guidance literature:: (6S)-methyl 6-C-allyl-4-O-benzyl-2,3-di-O-methyl-α-D-galactopyranoside; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 0.5h; Inert atmosphere;

methyl iodide; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 5h; Inert atmosphere;
DOI:10.1021/ja405588x

Reference yield:

: 64552-06-3
methyl 4,6-O-benzylidene-α-D-galactopyranoside

: 1454689-59-8
(6S)-methyl 6-C-allyl-4-O-benzyl-2,3,6-tri-O-methyl-α-D-galactopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium hydride / Inert atmosphere

2.1: borane-THF / dichloromethane / 0.75 h / 20 °C / Inert atmosphere

2.2: 5 h / 20 °C / Inert atmosphere

3.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 2.5 h / -78 °C / Inert atmosphere

3.2: 3 h / -78 - 20 °C / Inert atmosphere

4.1: tetrahydrofuran; diethyl ether / 5 h / -30 °C / Inert atmosphere

5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere

5.2: 5 h / 0 - 20 °C / Inert atmosphere

With borane-THF; oxalyl dichloride; sodium hydride; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; mineral oil; 3.1: |Swern Oxidation / 3.2: |Swern Oxidation;
DOI:10.1021/ja405588x

Reference yield:

: 51433-19-3,89177-22-0,129454-52-0,83075-53-0
methyl 4-O-benzyl-2,3-di-O-methyl-α-D-galactopyranoside

: 1454689-59-8
(6S)-methyl 6-C-allyl-4-O-benzyl-2,3,6-tri-O-methyl-α-D-galactopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 2.5 h / -78 °C / Inert atmosphere

1.2: 3 h / -78 - 20 °C / Inert atmosphere

2.1: tetrahydrofuran; diethyl ether / 5 h / -30 °C / Inert atmosphere

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere

3.2: 5 h / 0 - 20 °C / Inert atmosphere

With oxalyl dichloride; sodium hydride; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; mineral oil; 1.1: |Swern Oxidation / 1.2: |Swern Oxidation;
DOI:10.1021/ja405588x