6-benzyloxy-1-bromo-1,2,3-trideoxy-4,5:7,8-di-O-isopropylidene-D-erythro-D-manno-1-yno-octitol

Base Information

Chemical Name:6-benzyloxy-1-bromo-1,2,3-trideoxy-4,5:7,8-di-O-isopropylidene-D-erythro-D-manno-1-yno-octitol
CAS No.:1426261-18-8
Molecular Formula:C₂₁H₂₇BrO₅
Molecular Weight:439.346
Hs Code.:

Synonyms:6-benzyloxy-1-bromo-1,2,3-trideoxy-4,5:7,8-di-O-isopropylidene-D-erythro-D-manno-1-yno-octitol

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Chemical Property of 6-benzyloxy-1-bromo-1,2,3-trideoxy-4,5:7,8-di-O-isopropylidene-D-erythro-D-manno-1-yno-octitol

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Technology Process of 6-benzyloxy-1-bromo-1,2,3-trideoxy-4,5:7,8-di-O-isopropylidene-D-erythro-D-manno-1-yno-octitol

There total 7 articles about 6-benzyloxy-1-bromo-1,2,3-trideoxy-4,5:7,8-di-O-isopropylidene-D-erythro-D-manno-1-yno-octitol 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%

: 1426261-17-7
6-benzyloxy-1,2,3-trideoxy-4,5:7,8-di-O-isopropylidene-D-erythro-D-manno-1-yno-octitol

: 1426261-18-8
6-benzyloxy-1-bromo-1,2,3-trideoxy-4,5:7,8-di-O-isopropylidene-D-erythro-D-manno-1-yno-octitol

Guidance literature:: With N-Bromosuccinimide; silver nitrate; In acetone; at 0 - 20 ℃; for 1h;
DOI:10.1055/s-0032-1317932

Reference yield:

: 141410-34-6
5-O-Benzyl-1,2-dideoxy-3,4:6,7-di-O-isopropylidene-D-manno-hept-1-enitol

: 1426261-18-8
6-benzyloxy-1-bromo-1,2,3-trideoxy-4,5:7,8-di-O-isopropylidene-D-erythro-D-manno-1-yno-octitol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 4.5 h / 0 - 20 °C / Inert atmosphere

1.2: 6 h / 0 °C

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

2.2: -78 - 0 °C / Inert atmosphere

3.1: triphenylphosphine / dichloromethane / 1 h / 0 °C

3.2: 1 h / -78 - 0 °C / Inert atmosphere

4.1: N-Bromosuccinimide; silver nitrate / acetone / 1 h / 0 - 20 °C

With N-Bromosuccinimide; oxalyl dichloride; silver nitrate; dimethyl sulfoxide; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine; In tetrahydrofuran; dichloromethane; acetone; 2.1: |Swern Oxidation / 2.2: |Swern Oxidation / 3.1: |Corey-Fuchs Alkyne Synthesis / 3.2: |Corey-Fuchs Alkyne Synthesis;
DOI:10.1055/s-0032-1317932

Reference yield:

: 1426261-16-6
5-benzyloxy-2-deoxy-3,4:6,7-di-O-isopropylidene-D-erythro-D-manno-1-heptanol

: 1426261-18-8
6-benzyloxy-1-bromo-1,2,3-trideoxy-4,5:7,8-di-O-isopropylidene-D-erythro-D-manno-1-yno-octitol

Guidance literature:: Multi-step reaction with 3 steps

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

1.2: -78 - 0 °C / Inert atmosphere

2.1: triphenylphosphine / dichloromethane / 1 h / 0 °C

2.2: 1 h / -78 - 0 °C / Inert atmosphere

3.1: N-Bromosuccinimide; silver nitrate / acetone / 1 h / 0 - 20 °C

With N-Bromosuccinimide; oxalyl dichloride; silver nitrate; dimethyl sulfoxide; triphenylphosphine; In dichloromethane; acetone; 1.1: |Swern Oxidation / 1.2: |Swern Oxidation / 2.1: |Corey-Fuchs Alkyne Synthesis / 2.2: |Corey-Fuchs Alkyne Synthesis;
DOI:10.1055/s-0032-1317932