(2S,3S)-2,16-Dimethyl-3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-heptadecanoic acid

Base Information

Chemical Name:(2S,3S)-2,16-Dimethyl-3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-heptadecanoic acid
CAS No.:660403-62-3
Molecular Formula:C₄₆H₆₆O₈
Molecular Weight:747.025
Hs Code.:

Synonyms:(2S,3S)-2,16-Dimethyl-3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-heptadecanoic acid

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Chemical Property of (2S,3S)-2,16-Dimethyl-3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-heptadecanoic acid

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Technology Process of (2S,3S)-2,16-Dimethyl-3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-heptadecanoic acid

There total 4 articles about (2S,3S)-2,16-Dimethyl-3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-heptadecanoic acid 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: 50.0%

: 660403-82-7
(2S,3S)-3-((2R,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-2,16-dimethyl-heptadecanoic acid (1S,2R)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl ester

: 660403-62-3
(2S,3S)-2,16-Dimethyl-3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-heptadecanoic acid

Guidance literature:: With tetra(n-butyl)ammonium hydroxide; dihydrogen peroxide; In 1,2-dimethoxyethane; water; for 20h;
DOI:10.1021/jo035079f

Reference yield:

: 20194-48-3
14-methylpentadecan-1-ol

: 660403-62-3
(2S,3S)-2,16-Dimethyl-3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-heptadecanoic acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: 86 percent / pyridinium chlorochromate / CH₂Cl₂ / 2 h

2.1: dicyclohexylboron triflate; triethylamine / CH₂Cl₂; hexane / 2.33 h / -78 °C

2.2: 78 percent / CH₂Cl₂; hexane / 3 h / -78 - 20 °C

3.1: acetonitrile / 0.5 h / 20 °C

3.2: 46 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 2 h / -40 °C

4.1: 50 percent / (n-Bu)4NOH; H₂O₂ / H₂O; 1,2-dimethoxy-ethane / 20 h

With tetra(n-butyl)ammonium hydroxide; dihydrogen peroxide; triethylamine; pyridinium chlorochromate; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane; In 1,2-dimethoxyethane; hexane; dichloromethane; water; acetonitrile;
DOI:10.1021/jo035079f

Reference yield:

: 88591-08-6
14-methylpentadecanal

: 660403-62-3
(2S,3S)-2,16-Dimethyl-3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-heptadecanoic acid

Guidance literature:: Multi-step reaction with 3 steps

1.1: dicyclohexylboron triflate; triethylamine / CH₂Cl₂; hexane / 2.33 h / -78 °C

1.2: 78 percent / CH₂Cl₂; hexane / 3 h / -78 - 20 °C

2.1: acetonitrile / 0.5 h / 20 °C

2.2: 46 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 2 h / -40 °C

3.1: 50 percent / (n-Bu)4NOH; H₂O₂ / H₂O; 1,2-dimethoxy-ethane / 20 h

With tetra(n-butyl)ammonium hydroxide; dihydrogen peroxide; triethylamine; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane; In 1,2-dimethoxyethane; hexane; dichloromethane; water; acetonitrile;
DOI:10.1021/jo035079f