(3S,7S,9R)-9-benzyloxy-7-hydroxy-1,3-O-cyclohexylidene-3-methyldec-4-yne

Base Information

Chemical Name:(3S,7S,9R)-9-benzyloxy-7-hydroxy-1,3-O-cyclohexylidene-3-methyldec-4-yne
CAS No.:532437-78-8
Molecular Formula:C₂₄H₃₄O₄
Molecular Weight:386.532
Hs Code.:

Synonyms:(3S,7S,9R)-9-benzyloxy-7-hydroxy-1,3-O-cyclohexylidene-3-methyldec-4-yne

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Chemical Property of (3S,7S,9R)-9-benzyloxy-7-hydroxy-1,3-O-cyclohexylidene-3-methyldec-4-yne

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Technology Process of (3S,7S,9R)-9-benzyloxy-7-hydroxy-1,3-O-cyclohexylidene-3-methyldec-4-yne

There total 8 articles about (3S,7S,9R)-9-benzyloxy-7-hydroxy-1,3-O-cyclohexylidene-3-methyldec-4-yne 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: 87.0%

: 532437-63-1
(2R,4R)-4-benzyloxy-1,2-epoxypentane

: 532437-65-3
(S)-3-methyl-1,3-O-cyclohexylidenepent-4-yne

: 532437-78-8
(3S,7S,9R)-9-benzyloxy-7-hydroxy-1,3-O-cyclohexylidene-3-methyldec-4-yne

Guidance literature:: (S)-3-methyl-1,3-O-cyclohexylidenepent-4-yne; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.333333h;

(2R,4R)-4-benzyloxy-1,2-epoxypentane; With boron trifluoride diethyl etherate; In tetrahydrofuran; hexane; at -78 ℃; for 2h;
DOI:10.1016/S0957-4166(03)00040-5

Reference yield:

: 933-40-4
cycloxexanone dimethyl ketal

: 532437-78-8
(3S,7S,9R)-9-benzyloxy-7-hydroxy-1,3-O-cyclohexylidene-3-methyldec-4-yne

Guidance literature:: Multi-step reaction with 2 steps

1.1: 76 percent / p-TsOH*H₂O / CH₂Cl₂ / 3 h / 23 °C

2.1: nBuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

2.2: 87 percent / BF₃*OEt₂ / tetrahydrofuran; hexane / 2 h / -78 °C

With n-butyllithium; toluene-4-sulfonic acid; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1016/S0957-4166(03)00040-5

Reference yield:

: 532437-70-0
(2R,S_S)-2-hydroxy-1-(p-tolylsulfinyl)pentan-4-one

: 532437-78-8
(3S,7S,9R)-9-benzyloxy-7-hydroxy-1,3-O-cyclohexylidene-3-methyldec-4-yne

Guidance literature:: Multi-step reaction with 5 steps

1.1: Et₂BOMe; NaBH₄ / tetrahydrofuran; methanol / 6 h / -78 °C

1.2: 92 percent / aq. H₂O₂ / tetrahydrofuran; methanol / 10 h / -78 - 20 °C

2.1: p-TsOH*H₂O / CH₂Cl₂ / 1 h

3.1: 176 mg / DIBAL / CH₂Cl₂; hexane / 6 h / 20 °C

4.1: Me₃OBF₄ / CH₂Cl₂ / 2 h / 20 °C

4.2: 70 percent / aq. K₂CO₃ / CH₂Cl₂ / 30 h

5.1: nBuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

5.2: 87 percent / BF₃*OEt₂ / tetrahydrofuran; hexane / 2 h / -78 °C

With sodium tetrahydroborate; n-butyllithium; diethyl methoxy borane; trimethoxonium tetrafluoroborate; diisobutylaluminium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; hexane; dichloromethane;
DOI:10.1016/S0957-4166(03)00040-5