(2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2-O-palmitoyl-3-O-(tert-butyldimethylsilyl)glycerol

Base Information

Chemical Name:(2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2-O-palmitoyl-3-O-(tert-butyldimethylsilyl)glycerol
CAS No.:156832-41-6
Molecular Formula:C₅₉H₈₆O₉Si
Molecular Weight:967.412
Hs Code.:

Synonyms:(2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2-O-palmitoyl-3-O-(tert-butyldimethylsilyl)glycerol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2-O-palmitoyl-3-O-(tert-butyldimethylsilyl)glycerol

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Technology Process of (2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2-O-palmitoyl-3-O-(tert-butyldimethylsilyl)glycerol

There total 6 articles about (2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2-O-palmitoyl-3-O-(tert-butyldimethylsilyl)glycerol 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: 97.0%

: 623-65-4
palmitic anhydride

: 156832-40-5
(2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-3-O-(tert-butyldimethylsilyl)glycerol

: 156832-41-6
(2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2-O-palmitoyl-3-O-(tert-butyldimethylsilyl)glycerol

Guidance literature:: With dmap; triethylamine; In tetrahydrofuran; for 12h; Ambient temperature;
DOI:10.1021/jo00128a043

Reference yield: 66.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 156832-42-7
(2R)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2-O-palmitoylglycerol

: 156832-41-6
(2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2-O-palmitoyl-3-O-(tert-butyldimethylsilyl)glycerol

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; for 22h;
DOI:10.1021/jo00128a043

Reference yield:

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

: 156832-41-6
(2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2-O-palmitoyl-3-O-(tert-butyldimethylsilyl)glycerol

Guidance literature:: Multi-step reaction with 4 steps

1: 68 percent / NaH / tetrahydrofuran / 1.) -10 deg C, 30 min, 2.) -10 deg C, 7 h

2: 83 percent / 60percent aq. AcOH / 1.5 h / 103 °C

3: 88 percent / imidazole / dimethylformamide / 60 h / Ambient temperature

4: 97 percent / DMAP, Et₃N / tetrahydrofuran / 12 h / Ambient temperature

With 1H-imidazole; dmap; sodium hydride; acetic acid; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/jo00128a043