(3R,4R,5S,7R,13R,14S,16S)-4,13,14,16-Tetrakis-benzyloxy-5-hydroxy-3,7-dimethyl-17-(tetrahydro-pyran-2-yloxy)-heptadec-9-yn-8-one

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Chemical Name:(3R,4R,5S,7R,13R,14S,16S)-4,13,14,16-Tetrakis-benzyloxy-5-hydroxy-3,7-dimethyl-17-(tetrahydro-pyran-2-yloxy)-heptadec-9-yn-8-one
CAS No.:251353-61-4
Molecular Formula:C₅₂H₆₆O₈
Molecular Weight:819.091
Hs Code.:

Synonyms:(3R,4R,5S,7R,13R,14S,16S)-4,13,14,16-Tetrakis-benzyloxy-5-hydroxy-3,7-dimethyl-17-(tetrahydro-pyran-2-yloxy)-heptadec-9-yn-8-one

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Chemical Property of (3R,4R,5S,7R,13R,14S,16S)-4,13,14,16-Tetrakis-benzyloxy-5-hydroxy-3,7-dimethyl-17-(tetrahydro-pyran-2-yloxy)-heptadec-9-yn-8-one

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Technology Process of (3R,4R,5S,7R,13R,14S,16S)-4,13,14,16-Tetrakis-benzyloxy-5-hydroxy-3,7-dimethyl-17-(tetrahydro-pyran-2-yloxy)-heptadec-9-yn-8-one

There total 14 articles about (3R,4R,5S,7R,13R,14S,16S)-4,13,14,16-Tetrakis-benzyloxy-5-hydroxy-3,7-dimethyl-17-(tetrahydro-pyran-2-yloxy)-heptadec-9-yn-8-one 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: 72.0%

: 251353-50-1
(3R,5S)-5-((1R,2R)-1-Benzyloxy-2-methyl-butyl)-3-methyl-dihydro-furan-2-one

: 2-((2S,4S,5R)-2,4,5-Tris-benzyloxy-non-8-ynyloxy)-tetrahydro-pyran

: 251353-61-4
(3R,4R,5S,7R,13R,14S,16S)-4,13,14,16-Tetrakis-benzyloxy-5-hydroxy-3,7-dimethyl-17-(tetrahydro-pyran-2-yloxy)-heptadec-9-yn-8-one

Guidance literature:: With n-butyllithium; In diethyl ether; at -20 ℃;
DOI:10.1016/S0040-4039(99)01322-2

Reference yield:

: (2S,3R)-3-Benzyloxy-2-methyl-3-((S)-5-oxo-tetrahydro-furan-2-yl)-propionaldehyde

: 251353-61-4
(3R,4R,5S,7R,13R,14S,16S)-4,13,14,16-Tetrakis-benzyloxy-5-hydroxy-3,7-dimethyl-17-(tetrahydro-pyran-2-yloxy)-heptadec-9-yn-8-one

Guidance literature:: Multi-step reaction with 5 steps

1: n-BuLi / tetrahydrofuran

2: H₂ / Pd-C / ethyl acetate

3: TfOH / CH₂Cl₂; cyclohexane

4: 68 percent / LiHMDS / tetrahydrofuran / -78 °C

5: 72 percent / n-BuLi / diethyl ether / -20 °C

With n-butyllithium; trifluorormethanesulfonic acid; hydrogen; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; cyclohexane; ethyl acetate; 1: Condensation / 2: Catalytic hydrogenation / 3: Etherification / 4: Alkylation / 5: Acylation;
DOI:10.1016/S0040-4039(99)01322-2

Reference yield:

: 251353-68-1
(S)-5-((1R,2R)-1-Benzyloxy-3-hydroxy-2-methyl-propyl)-dihydro-furan-2-one

: 251353-61-4
(3R,4R,5S,7R,13R,14S,16S)-4,13,14,16-Tetrakis-benzyloxy-5-hydroxy-3,7-dimethyl-17-(tetrahydro-pyran-2-yloxy)-heptadec-9-yn-8-one

Guidance literature:: Multi-step reaction with 6 steps

2: n-BuLi / tetrahydrofuran

3: H₂ / Pd-C / ethyl acetate

4: TfOH / CH₂Cl₂; cyclohexane

5: 68 percent / LiHMDS / tetrahydrofuran / -78 °C

6: 72 percent / n-BuLi / diethyl ether / -20 °C

With n-butyllithium; trifluorormethanesulfonic acid; hydrogen; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; cyclohexane; ethyl acetate; 1: Oxidation / 2: Condensation / 3: Catalytic hydrogenation / 4: Etherification / 5: Alkylation / 6: Acylation;
DOI:10.1016/S0040-4039(99)01322-2