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

Base Information

Chemical Name:(3R,4R,5S,7R,13R,14S,16S)-4,13,14,16-Tetrakis-benzyloxy-3,7-dimethyl-17-(tetrahydro-pyran-2-yloxy)-heptadec-9-yne-5,8-diol
CAS No.:251353-72-7
Molecular Formula:C₅₂H₆₈O₈
Molecular Weight:821.107
Hs Code.:

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

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

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

There total 15 articles about (3R,4R,5S,7R,13R,14S,16S)-4,13,14,16-Tetrakis-benzyloxy-3,7-dimethyl-17-(tetrahydro-pyran-2-yloxy)-heptadec-9-yne-5,8-diol 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: 85.0%

: 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

: 251353-72-7
(3R,4R,5S,7R,13R,14S,16S)-4,13,14,16-Tetrakis-benzyloxy-3,7-dimethyl-17-(tetrahydro-pyran-2-yloxy)-heptadec-9-yne-5,8-diol

Guidance literature:: With sodium tetrahydroborate; cerium(III) chloride; In methanol;
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

: 251353-72-7
(3R,4R,5S,7R,13R,14S,16S)-4,13,14,16-Tetrakis-benzyloxy-3,7-dimethyl-17-(tetrahydro-pyran-2-yloxy)-heptadec-9-yne-5,8-diol

Guidance literature:: Multi-step reaction with 6 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

6: 85 percent / NaBH₄; CeCl₃ / methanol

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

Reference yield:

: 251353-58-9
(S)-5-((1R,2R)-1-Benzyloxy-2-methyl-but-3-enyl)-dihydro-furan-2-one

: 251353-72-7
(3R,4R,5S,7R,13R,14S,16S)-4,13,14,16-Tetrakis-benzyloxy-3,7-dimethyl-17-(tetrahydro-pyran-2-yloxy)-heptadec-9-yne-5,8-diol

Guidance literature:: Multi-step reaction with 5 steps

1: H₂ / Pd-C / ethyl acetate

2: TfOH / CH₂Cl₂; cyclohexane

3: 68 percent / LiHMDS / tetrahydrofuran / -78 °C

4: 72 percent / n-BuLi / diethyl ether / -20 °C

5: 85 percent / NaBH₄; CeCl₃ / methanol

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