1-bromo-3,6-di-O-benzyl-1,2-dideoxy-4,5:7,8-di-O-isopropylidene-D-glycero-D-galacto-1-yno-octitol

Base Information

Chemical Name:1-bromo-3,6-di-O-benzyl-1,2-dideoxy-4,5:7,8-di-O-isopropylidene-D-glycero-D-galacto-1-yno-octitol
CAS No.:1569902-08-4
Molecular Formula:C₂₈H₃₃BrO₆
Molecular Weight:545.47
Hs Code.:

Synonyms:1-bromo-3,6-di-O-benzyl-1,2-dideoxy-4,5:7,8-di-O-isopropylidene-D-glycero-D-galacto-1-yno-octitol

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Chemical Property of 1-bromo-3,6-di-O-benzyl-1,2-dideoxy-4,5:7,8-di-O-isopropylidene-D-glycero-D-galacto-1-yno-octitol

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Technology Process of 1-bromo-3,6-di-O-benzyl-1,2-dideoxy-4,5:7,8-di-O-isopropylidene-D-glycero-D-galacto-1-yno-octitol

There total 4 articles about 1-bromo-3,6-di-O-benzyl-1,2-dideoxy-4,5:7,8-di-O-isopropylidene-D-glycero-D-galacto-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: 80.0%

: 1569902-07-3
3,6-di-O-benzyl-1,2-dideoxy-4,5:7,8-di-O-isopropylidene-D-glycero-D-galacto-1-yno-octitol

: 1569902-08-4
1-bromo-3,6-di-O-benzyl-1,2-dideoxy-4,5:7,8-di-O-isopropylidene-D-glycero-D-galacto-1-yno-octitol

Guidance literature:: With N-Bromosuccinimide; silver nitrate; In acetone; at 0 - 20 ℃; for 0.5h;
DOI:10.1021/ol500275j

Reference yield:

: 7757-38-2,14131-84-1,23262-78-4,27108-13-0,33823-04-0,34685-42-2,57819-52-0,78039-08-4,78039-12-0,78964-16-6,94842-76-9,149342-31-4
2,3:5,6-di-O-isopropylidene-D-mannofuranose

: 1569902-08-4
1-bromo-3,6-di-O-benzyl-1,2-dideoxy-4,5:7,8-di-O-isopropylidene-D-glycero-D-galacto-1-yno-octitol

Guidance literature:: Multi-step reaction with 4 steps

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

1.2: 19 h / -40 - 0 °C / Inert atmosphere

2.1: cesium fluoride / acetonitrile; water / 2 h / 0 - 20 °C

3.1: sodium hydride / mineral oil; tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

3.2: 1 h / 20 °C / Inert atmosphere

4.1: N-Bromosuccinimide; silver nitrate / acetone / 0.5 h / 0 - 20 °C

With N-Bromosuccinimide; n-butyllithium; sodium hydride; silver nitrate; cesium fluoride; In tetrahydrofuran; water; acetone; acetonitrile; mineral oil;
DOI:10.1021/ol500275j

Reference yield:

: 31024-99-4,54187-72-3,76249-79-1
1,2-dideoxy-4,5:7,8-di-O-isopropylidene-D-erythro-D-manno-1-yno-octitol

: 1569902-08-4
1-bromo-3,6-di-O-benzyl-1,2-dideoxy-4,5:7,8-di-O-isopropylidene-D-glycero-D-galacto-1-yno-octitol

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium hydride / mineral oil; tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

1.2: 1 h / 20 °C / Inert atmosphere

2.1: N-Bromosuccinimide; silver nitrate / acetone / 0.5 h / 0 - 20 °C

With N-Bromosuccinimide; sodium hydride; silver nitrate; In tetrahydrofuran; acetone; mineral oil;
DOI:10.1021/ol500275j