4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-galactopyranose 1-O-trichloroacetimidate

Base Information

Chemical Name:4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-galactopyranose 1-O-trichloroacetimidate
CAS No.:130257-35-1
Molecular Formula:C₂₄H₂₅Cl₃N₄O₆
Molecular Weight:571.845
Hs Code.:

Synonyms:4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-galactopyranose 1-O-trichloroacetimidate

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Chemical Property of 4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-galactopyranose 1-O-trichloroacetimidate

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Technology Process of 4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-galactopyranose 1-O-trichloroacetimidate

There total 6 articles about 4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-galactopyranose 1-O-trichloroacetimidate 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: 86.0%

: 4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-D-galactopyranose

: 545-06-2
trichloroacetonitrile

: 130257-35-1
4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-galactopyranose 1-O-trichloroacetimidate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 - 20 ℃; for 3h;
DOI:10.1021/jo1025157

Reference yield:

: 1310050-37-3
C₂₀H₂₁N₃O₄S

: 130257-35-1
4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-galactopyranose 1-O-trichloroacetimidate

Guidance literature:: Multi-step reaction with 5 steps

1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C

2: hydrogenchloride; sodium cyanoborohydride / tetrahydrofuran; 1,4-dioxane; water / 2 h / 0 °C / Molecular sieve; Inert atmosphere

3: triethylamine / dichloromethane / 0.5 h / 20 °C

4: N-Bromosuccinimide; water / acetone / 20 °C

5: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 3 h / 0 - 20 °C

With hydrogenchloride; N-Bromosuccinimide; water; sodium hydride; sodium cyanoborohydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; acetone; mineral oil;
DOI:10.1021/jo1025157

Reference yield:

: 100-39-0
benzyl bromide

: 130257-35-1
4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-galactopyranose 1-O-trichloroacetimidate

Guidance literature:: Multi-step reaction with 5 steps

1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C

2: hydrogenchloride; sodium cyanoborohydride / tetrahydrofuran; 1,4-dioxane; water / 2 h / 0 °C / Molecular sieve; Inert atmosphere

3: triethylamine / dichloromethane / 0.5 h / 20 °C

4: N-Bromosuccinimide; water / acetone / 20 °C

5: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 3 h / 0 - 20 °C

With hydrogenchloride; N-Bromosuccinimide; water; sodium hydride; sodium cyanoborohydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; acetone; mineral oil;
DOI:10.1021/jo1025157