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

Base Information

Chemical Name:5-O-Benzyl-1,2-dideoxy-3,4:6,7-di-O-isopropylidene-D-manno-hept-1-enitol
CAS No.:141410-34-6
Molecular Formula:C₂₀H₂₈O₅
Molecular Weight:348.439
Hs Code.:

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

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Chemical Property of 5-O-Benzyl-1,2-dideoxy-3,4:6,7-di-O-isopropylidene-D-manno-hept-1-enitol

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Technology Process of 5-O-Benzyl-1,2-dideoxy-3,4:6,7-di-O-isopropylidene-D-manno-hept-1-enitol

There total 3 articles about 5-O-Benzyl-1,2-dideoxy-3,4:6,7-di-O-isopropylidene-D-manno-hept-1-enitol 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%

: 100-39-0
benzyl bromide

: 137945-76-7
(R)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl][(4S,5R)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]methanol

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

Guidance literature:: (R)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl][(4S,5R)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]methanol; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 0.166667h;

benzyl bromide; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; for 2h;
DOI:10.1021/acs.orglett.1c00720

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

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

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) BuLi / 1.) THF, hexane, -5 to -10 deg C, 1 h; 2.) THF, r.t., overnight

2: 1.) NaH / 1.) DMF, 0 deg C, 1 h; 2.) r.t., overnight

With n-butyllithium; sodium hydride;
DOI:10.1016/0008-6215(92)84055-W

Reference yield:

: 14131-84-1
2,3:5,6-di-O-isopropylidene-α-D-mannofuranose

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

Guidance literature:: Multi-step reaction with 2 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere

1.2: 2 h / 0 - 20 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C

2.2: 2 h / 0 - 20 °C

With sodium hydride; lithium hexamethyldisilazane; In tetrahydrofuran; mineral oil;
DOI:10.1021/acs.orglett.1c00720