(2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2,3-O-isopropylideneglycerol

Base Information

Chemical Name:(2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2,3-O-isopropylideneglycerol
CAS No.:156925-78-9
Molecular Formula:C₄₀H₄₆O₈
Molecular Weight:654.8
Hs Code.:

Synonyms:(2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2,3-O-isopropylideneglycerol

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Chemical Property of (2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2,3-O-isopropylideneglycerol

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Technology Process of (2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2,3-O-isopropylideneglycerol

There total 1 articles about (2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2,3-O-isopropylideneglycerol 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:

: 59531-24-7
2,3,4,6-tetra-O-benzyl-D-glucopyranoside

: 156925-79-0
[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl trifluoromethanesulfonate

: 156925-78-9
(2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2,3-O-isopropylideneglycerol

: (2S)-1-O-(2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl)-2,3-O-isopropylideneglycerol

Guidance literature:: With sodium hydride; In tetrahydrofuran; Yield given; 1.) -10 deg C, 1 h, 2.) -10 to -15 deg C, 6 h;
DOI:10.1021/jo00128a043

Reference yield: 96.0%

: 156925-78-9
(2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2,3-O-isopropylideneglycerol

: 156832-48-3
(2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)glycerol

Guidance literature:: With acetic acid; for 1h; Heating;
DOI:10.1021/jo00128a043

Reference yield:

: 156925-78-9
(2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2,3-O-isopropylideneglycerol

: 156832-54-1
(2R)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2-O-palmitoyl-3-O-phosphatidylcholinylglycerol

Guidance literature:: Multi-step reaction with 7 steps

1: 96 percent / 60percent aq. AcOH / 1 h / Heating

2: 90 percent / imidazole / dimethylformamide / Ambient temperature

3: 96 percent / DMAP, Et₃N / tetrahydrofuran / Ambient temperature

4: 11.6 percent / glac. AcOH, TBAF / tetrahydrofuran / 0.5 h

5: Et₃N / diethyl ether / 1.5 h

6: tetrahydrofuran / 16 h / Ambient temperature

7: 21 percent / benzene / 24 h / 55 °C

With 1H-imidazole; dmap; tetrabutyl ammonium fluoride; acetic acid; triethylamine; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo00128a043