Hexadecanoic acid (S)-1-[(2-bromo-ethoxy)-chloro-phosphoryloxymethyl]-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-ethyl ester

Base Information

Chemical Name:Hexadecanoic acid (S)-1-[(2-bromo-ethoxy)-chloro-phosphoryloxymethyl]-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-ethyl ester
CAS No.:1053700-96-1
Molecular Formula:C₅₅H₇₅BrClO₁₁P
Molecular Weight:1058.52
Hs Code.:

Hexadecanoic acid (S)-1-[(2-bromo-ethoxy)-chloro-phosphoryloxymethyl]-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-ethyl ester

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Chemical Property of Hexadecanoic acid (S)-1-[(2-bromo-ethoxy)-chloro-phosphoryloxymethyl]-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-ethyl ester

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Technology Process of Hexadecanoic acid (S)-1-[(2-bromo-ethoxy)-chloro-phosphoryloxymethyl]-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-ethyl ester

There total 7 articles about Hexadecanoic acid (S)-1-[(2-bromo-ethoxy)-chloro-phosphoryloxymethyl]-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-ethyl ester 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:

: 623-65-4
palmitic anhydride

: 1053700-96-1
Hexadecanoic acid (S)-1-[(2-bromo-ethoxy)-chloro-phosphoryloxymethyl]-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-ethyl ester

Guidance literature:: Multi-step reaction with 3 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

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

Reference yield:

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

: 1053700-96-1
Hexadecanoic acid (S)-1-[(2-bromo-ethoxy)-chloro-phosphoryloxymethyl]-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-ethyl ester

Guidance literature:: Multi-step reaction with 6 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

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

Reference yield:

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

: 1053700-96-1
Hexadecanoic acid (S)-1-[(2-bromo-ethoxy)-chloro-phosphoryloxymethyl]-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-ethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 15 percent / glac. AcOH, TBAF / tetrahydrofuran / 0.75 h

2: Et₃N / diethyl ether / 0.5 h

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