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

Base Information

Chemical Name:(2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2-O-palmitoyl-3-O-phosphatidylcholinylglycerol
CAS No.:156832-46-1
Molecular Formula:C₅₈H₈₄NO₁₂P
Molecular Weight:1018.28
Hs Code.:

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

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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-phosphatidylcholinylglycerol

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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-phosphatidylcholinylglycerol

There total 9 articles about (2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2-O-palmitoyl-3-O-phosphatidylcholinylglycerol 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: 45.5%

: 156832-45-0
(2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2-O-palmitoyl-3-O-<(2-bromoethoxy)benzoxyphosphoryl>glycerol

: 75-50-3
trimethylamine

: 156832-46-1
(2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2-O-palmitoyl-3-O-phosphatidylcholinylglycerol

Guidance literature:: In toluene; at 55 ℃; for 24h;
DOI:10.1021/jo00128a043

Reference yield:

: 623-65-4
palmitic anhydride

: 156832-46-1
(2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2-O-palmitoyl-3-O-phosphatidylcholinylglycerol

Guidance literature:: Multi-step reaction with 5 steps

1: 97 percent / DMAP, Et₃N / tetrahydrofuran / 12 h / Ambient temperature

2: 15 percent / glac. AcOH, TBAF / tetrahydrofuran / 0.75 h

3: Et₃N / diethyl ether / 0.5 h

4: tetrahydrofuran / 120 h / Ambient temperature

5: 45.5 percent / toluene / 24 h / 55 °C

With dmap; tetrabutyl ammonium fluoride; acetic acid; triethylamine; In tetrahydrofuran; diethyl ether; toluene;
DOI:10.1021/jo00128a043

Reference yield:

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

: 156832-46-1
(2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2-O-palmitoyl-3-O-phosphatidylcholinylglycerol

Guidance literature:: Multi-step reaction with 8 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

5: 15 percent / glac. AcOH, TBAF / tetrahydrofuran / 0.75 h

6: Et₃N / diethyl ether / 0.5 h

7: tetrahydrofuran / 120 h / Ambient temperature

8: 45.5 percent / toluene / 24 h / 55 °C

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