Acetic acid (S)-((1R,3S)-3-benzyloxy-4,4-dimethyl-2-oxo-cyclopentyl)-(1-methyl-cyclohexa-2,5-dienyl)-methyl ester

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Chemical Name:Acetic acid (S)-((1R,3S)-3-benzyloxy-4,4-dimethyl-2-oxo-cyclopentyl)-(1-methyl-cyclohexa-2,5-dienyl)-methyl ester
CAS No.:177315-34-3
Molecular Formula:C₂₄H₃₀O₄
Molecular Weight:382.5
Hs Code.:

Synonyms:Acetic acid (S)-((1R,3S)-3-benzyloxy-4,4-dimethyl-2-oxo-cyclopentyl)-(1-methyl-cyclohexa-2,5-dienyl)-methyl ester

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Chemical Property of Acetic acid (S)-((1R,3S)-3-benzyloxy-4,4-dimethyl-2-oxo-cyclopentyl)-(1-methyl-cyclohexa-2,5-dienyl)-methyl ester

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Technology Process of Acetic acid (S)-((1R,3S)-3-benzyloxy-4,4-dimethyl-2-oxo-cyclopentyl)-(1-methyl-cyclohexa-2,5-dienyl)-methyl ester

There total 8 articles about Acetic acid (S)-((1R,3S)-3-benzyloxy-4,4-dimethyl-2-oxo-cyclopentyl)-(1-methyl-cyclohexa-2,5-dienyl)-methyl 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: 95.0%

: 108-24-7
acetic anhydride

: 177315-43-4
(2S,5R)-2-Benzyloxy-5-[(S)-hydroxy-(1-methyl-cyclohexa-2,5-dienyl)-methyl]-3,3-dimethyl-cyclopentanone

: 177315-34-3
Acetic acid (S)-((1R,3S)-3-benzyloxy-4,4-dimethyl-2-oxo-cyclopentyl)-(1-methyl-cyclohexa-2,5-dienyl)-methyl ester

Guidance literature:: With pyridine; dmap; for 1h; Ambient temperature;
DOI:10.1016/0040-4020(96)00270-0

Reference yield:

: 59034-54-7
1-methyl-cyclohexa-2,5-dienecarboxylic acid methyl ester

: 177315-34-3
Acetic acid (S)-((1R,3S)-3-benzyloxy-4,4-dimethyl-2-oxo-cyclopentyl)-(1-methyl-cyclohexa-2,5-dienyl)-methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 100 percent / LiAlH₄ / tetrahydrofuran / 0.25 h / Ambient temperature

2: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 15 min, 2.) CH₂Cl₂, from -60 to 0 deg C, 3 min

3: 1.) diisopropyl amine, n-BuLi / 1.) THF, -40 deg C, 1 h, 2.) THF, -78 deg C, 5 min

4: 95 percent / pyridine, DMAP / 1 h / Ambient temperature

With pyridine; dmap; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; diisopropylamine; In tetrahydrofuran;
DOI:10.1016/0040-4020(96)00270-0

Reference yield:

: 100-39-0
benzyl bromide

: 177315-34-3
Acetic acid (S)-((1R,3S)-3-benzyloxy-4,4-dimethyl-2-oxo-cyclopentyl)-(1-methyl-cyclohexa-2,5-dienyl)-methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) NaH / 1.) DMF, RT, 15 min, 2.) DMF, 15 min

2: 90 percent / CaCO₃, aq. HgCl₂ / acetone; H₂O / 2 h / Heating

3: 1.) diisopropyl amine, n-BuLi / 1.) THF, -40 deg C, 1 h, 2.) THF, -78 deg C, 5 min

4: 95 percent / pyridine, DMAP / 1 h / Ambient temperature

With pyridine; dmap; n-butyllithium; sodium hydride; diisopropylamine; calcium carbonate; mercury dichloride; In water; acetone;
DOI:10.1016/0040-4020(96)00270-0