(4aR,8aS)-3a-Hydroxy-6,8b-dimethyl-1-oxo-2-phenylsulfanyl-2,3,3a,7,8,8b-hexahydro-1H,4aH-benzo[b]cyclopenta[d]furan-8a-carboxylic acid methyl ester

Base Information

Chemical Name:(4aR,8aS)-3a-Hydroxy-6,8b-dimethyl-1-oxo-2-phenylsulfanyl-2,3,3a,7,8,8b-hexahydro-1H,4aH-benzo[b]cyclopenta[d]furan-8a-carboxylic acid methyl ester
CAS No.:87902-46-3
Molecular Formula:C₂₁H₂₄O₅S
Molecular Weight:388.485
Hs Code.:

(4aR,8aS)-3a-Hydroxy-6,8b-dimethyl-1-oxo-2-phenylsulfanyl-2,3,3a,7,8,8b-hexahydro-1H,4aH-benzo[b]cyclopenta[d]furan-8a-carboxylic acid methyl ester

Synonyms:(4aR,8aS)-3a-Hydroxy-6,8b-dimethyl-1-oxo-2-phenylsulfanyl-2,3,3a,7,8,8b-hexahydro-1H,4aH-benzo[b]cyclopenta[d]furan-8a-carboxylic acid methyl ester

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Chemical Property of (4aR,8aS)-3a-Hydroxy-6,8b-dimethyl-1-oxo-2-phenylsulfanyl-2,3,3a,7,8,8b-hexahydro-1H,4aH-benzo[b]cyclopenta[d]furan-8a-carboxylic acid methyl ester

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Technology Process of (4aR,8aS)-3a-Hydroxy-6,8b-dimethyl-1-oxo-2-phenylsulfanyl-2,3,3a,7,8,8b-hexahydro-1H,4aH-benzo[b]cyclopenta[d]furan-8a-carboxylic acid methyl ester

There total 6 articles about (4aR,8aS)-3a-Hydroxy-6,8b-dimethyl-1-oxo-2-phenylsulfanyl-2,3,3a,7,8,8b-hexahydro-1H,4aH-benzo[b]cyclopenta[d]furan-8a-carboxylic acid 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:

: 52062-24-5
(E)-1-acetoxy-3-methyl-1,3-butadiene

: 87902-46-3
(4aR,8aS)-3a-Hydroxy-6,8b-dimethyl-1-oxo-2-phenylsulfanyl-2,3,3a,7,8,8b-hexahydro-1H,4aH-benzo[b]cyclopenta[d]furan-8a-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 47.2 percent / n-butyllithium / hexane; tetrahydrofuran / 0.5 h / 0 °C

2: 87.6 percent Turnov_. / BSA / 20 h / 127 - 129 °C

3: trifluoroacetic acid / CH₂Cl₂ / 3 h / 0 °C

4: 1.) LDA / 1.) THF, hexane, 10 min, -78 deg C -> 0 deg C, 15 min; 2.) HMPA, r.t.

With benzenesulfonamide; n-butyllithium; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ja00314a023

Reference yield:

: 58274-64-9,82223-93-6,73912-36-4
(E)-trimethyl((3-methylbuta-1,3-dien-1-yl)oxy)silane

: 87902-46-3
(4aR,8aS)-3a-Hydroxy-6,8b-dimethyl-1-oxo-2-phenylsulfanyl-2,3,3a,7,8,8b-hexahydro-1H,4aH-benzo[b]cyclopenta[d]furan-8a-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 87.6 percent Turnov_. / BSA / 20 h / 127 - 129 °C

2: trifluoroacetic acid / CH₂Cl₂ / 3 h / 0 °C

3: 1.) LDA / 1.) THF, hexane, 10 min, -78 deg C -> 0 deg C, 15 min; 2.) HMPA, r.t.

With benzenesulfonamide; trifluoroacetic acid; lithium diisopropyl amide; In dichloromethane;
DOI:10.1021/ja00314a023

Reference yield:

: 87902-37-2
3-Chloro-2-(1-methyl-2,5-dioxo-cyclopentyl)-propionic acid methyl ester

: 87902-46-3
(4aR,8aS)-3a-Hydroxy-6,8b-dimethyl-1-oxo-2-phenylsulfanyl-2,3,3a,7,8,8b-hexahydro-1H,4aH-benzo[b]cyclopenta[d]furan-8a-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: DBU / benzene; diethyl ether / 0.33 h / Ambient temperature

2: 87.6 percent Turnov_. / BSA / 20 h / 127 - 129 °C

3: trifluoroacetic acid / CH₂Cl₂ / 3 h / 0 °C

4: 1.) LDA / 1.) THF, hexane, 10 min, -78 deg C -> 0 deg C, 15 min; 2.) HMPA, r.t.

With benzenesulfonamide; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; lithium diisopropyl amide; In diethyl ether; dichloromethane; benzene;
DOI:10.1021/ja00314a023