2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-3,4,6-tri-O-benzyl-α-D-glucopyranosyl bromide

Base Information

Chemical Name:2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-3,4,6-tri-O-benzyl-α-D-glucopyranosyl bromide
CAS No.:1254190-93-6
Molecular Formula:C₃₉H₄₅BrO₁₂
Molecular Weight:785.683
Hs Code.:

Synonyms:2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-3,4,6-tri-O-benzyl-α-D-glucopyranosyl bromide

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Chemical Property of 2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-3,4,6-tri-O-benzyl-α-D-glucopyranosyl bromide

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Technology Process of 2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-3,4,6-tri-O-benzyl-α-D-glucopyranosyl bromide

There total 7 articles about 2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-3,4,6-tri-O-benzyl-α-D-glucopyranosyl bromide 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: 90.0%

: 1254190-92-5
1-O-acetyl-2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-3,4,6-tri-O-benzyl-D-glucopyranose

: 1254190-93-6
2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-3,4,6-tri-O-benzyl-α-D-glucopyranosyl bromide

Guidance literature:: With hydrogen bromide; acetic acid; In dichloromethane; water; at 20 ℃; for 0.5h; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/ml100171x

Reference yield:

: 55628-54-1
3,4,6-tri-O-benzyl-D-glucal

: 1254190-93-6
2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-3,4,6-tri-O-benzyl-α-D-glucopyranosyl bromide

Guidance literature:: Multi-step reaction with 3 steps

1.1: 3,3-dimethyldioxirane / acetone / 6 h / 0 °C / Inert atmosphere

1.2: 12 h / 20 °C / Inert atmosphere

2.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 12 h / 20 °C / Inert atmosphere

3.1: hydrogen bromide; acetic acid / dichloromethane; water / 0.5 h / 20 °C / Inert atmosphere

With trimethylsilyl trifluoromethanesulfonate; hydrogen bromide; 3,3-dimethyldioxirane; acetic acid; In dichloromethane; water; acetone;
DOI:10.1021/ml100171x

Reference yield:

: 28915-80-2,40591-53-5,40591-54-6,40591-55-7,120449-19-6,120449-20-9,143332-42-7,148081-39-4,151413-57-9,151413-58-0
2,3,4-tri-O-acetyl-L-rhamnopyranose

: 1254190-93-6
2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-3,4,6-tri-O-benzyl-α-D-glucopyranosyl bromide

Guidance literature:: Multi-step reaction with 3 steps

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.5 h / 20 °C

2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 12 h / 20 °C / Inert atmosphere

3: hydrogen bromide; acetic acid / dichloromethane; water / 0.5 h / 20 °C / Inert atmosphere

With trimethylsilyl trifluoromethanesulfonate; hydrogen bromide; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; water;
DOI:10.1021/ml100171x