methyl 2,3-di-O-benzyl-4-deoxy-4-C-[(1R)-1-triethylsilyloxyallyl]-6-O-p-methoxybenzyl-α-D-galactopyranoside

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Chemical Name:methyl 2,3-di-O-benzyl-4-deoxy-4-C-[(1R)-1-triethylsilyloxyallyl]-6-O-p-methoxybenzyl-α-D-galactopyranoside
CAS No.:1610594-33-6
Molecular Formula:C₃₈H₅₂O₇Si
Molecular Weight:648.912
Hs Code.:

Synonyms:methyl 2,3-di-O-benzyl-4-deoxy-4-C-[(1R)-1-triethylsilyloxyallyl]-6-O-p-methoxybenzyl-α-D-galactopyranoside

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Chemical Property of methyl 2,3-di-O-benzyl-4-deoxy-4-C-[(1R)-1-triethylsilyloxyallyl]-6-O-p-methoxybenzyl-α-D-galactopyranoside

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Technology Process of methyl 2,3-di-O-benzyl-4-deoxy-4-C-[(1R)-1-triethylsilyloxyallyl]-6-O-p-methoxybenzyl-α-D-galactopyranoside

There total 5 articles about methyl 2,3-di-O-benzyl-4-deoxy-4-C-[(1R)-1-triethylsilyloxyallyl]-6-O-p-methoxybenzyl-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: 85.0%

: 994-30-9
triethylsilyl chloride

: 1610594-32-5
methyl 2,3-di-O-benzyl-4-deoxy-4-C-((1R/S)-1-hydroxyallyl)-6-O-p-methoxybenzyl-α-D-galactopyranoside

: 1610594-33-6
methyl 2,3-di-O-benzyl-4-deoxy-4-C-[(1R)-1-triethylsilyloxyallyl]-6-O-p-methoxybenzyl-α-D-galactopyranoside

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 60 ℃; for 1.5h;
DOI:10.1002/ejoc.201400028

Reference yield:

: 1779-49-3
Methyltriphenylphosphonium bromide

: 1610594-33-6
methyl 2,3-di-O-benzyl-4-deoxy-4-C-[(1R)-1-triethylsilyloxyallyl]-6-O-p-methoxybenzyl-α-D-galactopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

2.1: dimethylsulfide borane complex / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere

2.2: 12 h / 0 - 20 °C

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

3.2: 0.5 h / -78 - 0 °C / Inert atmosphere

4.1: tetrahydrofuran / 1.5 h / -78 °C / Inert atmosphere

5.1: 1H-imidazole / N,N-dimethyl-formamide / 1.5 h / 60 °C

With 1H-imidazole; n-butyllithium; oxalyl dichloride; dimethylsulfide borane complex; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1.1: |Wittig Olefination / 3.1: |Swern Oxidation / 4.1: |Grignard Reaction;
DOI:10.1002/ejoc.201400028

Reference yield:

: 203118-63-2
methyl 2,3-di-O-benzyl-4-deoxy-4-C-methylene-6-O-p-methoxybenzyl-α-D-xylo-hexopyranoside

: 1610594-33-6
methyl 2,3-di-O-benzyl-4-deoxy-4-C-[(1R)-1-triethylsilyloxyallyl]-6-O-p-methoxybenzyl-α-D-galactopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: dimethylsulfide borane complex / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere

1.2: 12 h / 0 - 20 °C

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

2.2: 0.5 h / -78 - 0 °C / Inert atmosphere

3.1: tetrahydrofuran / 1.5 h / -78 °C / Inert atmosphere

4.1: 1H-imidazole / N,N-dimethyl-formamide / 1.5 h / 60 °C

With 1H-imidazole; oxalyl dichloride; dimethylsulfide borane complex; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 2.1: |Swern Oxidation / 3.1: |Grignard Reaction;
DOI:10.1002/ejoc.201400028