methyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranoside

Base Information

Chemical Name:methyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranoside
CAS No.:1355357-15-1
Molecular Formula:C₃₂H₃₁N₃O₆
Molecular Weight:553.615
Hs Code.:

Synonyms:methyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranoside

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Chemical Property of methyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranoside

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Technology Process of methyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranoside

There total 9 articles about methyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranoside 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: 94.0%

: 1355357-16-2
methyl 2-azido-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranoside

: 98-88-4
benzoyl chloride

: 1355357-15-1
methyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranoside

Guidance literature:: With dmap; triethylamine; In dichloromethane; for 2h; Inert atmosphere;
DOI:10.1039/c1ob06415k

Reference yield:

: 100-39-0
benzyl bromide

: 1355357-15-1
methyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: silver(l) oxide / dichloromethane / 48 h / 0 - 20 °C / Inert atmosphere; Cooling with ice

2.1: borane-THF; trimethylsilyl trifluoromethanesulfonate / tetrahydrofuran; dichloromethane / 4 h / 0 °C / Inert atmosphere

2.2: Inert atmosphere; Cooling with ice

3.1: boron trifluoride diethyl etherate / 6 h / 0 - 55 °C / Inert atmosphere

4.1: dmap; triethylamine / dichloromethane / 2 h / Inert atmosphere

With dmap; borane-THF; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; triethylamine; silver(l) oxide; In tetrahydrofuran; dichloromethane;
DOI:10.1039/c1ob06415k

Reference yield:

: C₂₃H₃₃N₃O₅Si₂

: 1355357-15-1
methyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: tetrabutyl ammonium fluoride; benzoic acid / 0 °C

2.1: triethylamine

3.1: silver(l) oxide / dichloromethane / 48 h / 0 - 20 °C / Inert atmosphere; Cooling with ice

4.1: borane-THF; trimethylsilyl trifluoromethanesulfonate / tetrahydrofuran; dichloromethane / 4 h / 0 °C / Inert atmosphere

4.2: Inert atmosphere; Cooling with ice

5.1: boron trifluoride diethyl etherate / 6 h / 0 - 55 °C / Inert atmosphere

6.1: dmap; triethylamine / dichloromethane / 2 h / Inert atmosphere

With dmap; borane-THF; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; triethylamine; benzoic acid; silver(l) oxide; In tetrahydrofuran; dichloromethane;
DOI:10.1039/c1ob06415k