(1S,5R,7aS)-7a-methyl-4-phenylthio-1-{(1S)-2-[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]-1-(tosyloxymethyl)ethyl}-2,3,5,6,7,7a-hexahydro-1H-inden-5-ol

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Chemical Name:(1S,5R,7aS)-7a-methyl-4-phenylthio-1-{(1S)-2-[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]-1-(tosyloxymethyl)ethyl}-2,3,5,6,7,7a-hexahydro-1H-inden-5-ol
CAS No.:343969-50-6
Molecular Formula:C₃₃H₄₄O₆S₂
Molecular Weight:600.841
Hs Code.:

Synonyms:(1S,5R,7aS)-7a-methyl-4-phenylthio-1-{(1S)-2-[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]-1-(tosyloxymethyl)ethyl}-2,3,5,6,7,7a-hexahydro-1H-inden-5-ol

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Chemical Property of (1S,5R,7aS)-7a-methyl-4-phenylthio-1-{(1S)-2-[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]-1-(tosyloxymethyl)ethyl}-2,3,5,6,7,7a-hexahydro-1H-inden-5-ol

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Technology Process of (1S,5R,7aS)-7a-methyl-4-phenylthio-1-{(1S)-2-[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]-1-(tosyloxymethyl)ethyl}-2,3,5,6,7,7a-hexahydro-1H-inden-5-ol

There total 9 articles about (1S,5R,7aS)-7a-methyl-4-phenylthio-1-{(1S)-2-[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]-1-(tosyloxymethyl)ethyl}-2,3,5,6,7,7a-hexahydro-1H-inden-5-ol 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: 78.0%

: 98-59-9
p-toluenesulfonyl chloride

: 681180-39-2
(1S,5R,7aS)-1-{(1S)-1-(hydroxymethyl)ethyl-2-[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]}-7a-methyl-4-phenylthio-2,3,5,6,7,7a-hexahydro-1H-inden-5-ol

: 343969-50-6
(1S,5R,7aS)-7a-methyl-4-phenylthio-1-{(1S)-2-[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]-1-(tosyloxymethyl)ethyl}-2,3,5,6,7,7a-hexahydro-1H-inden-5-ol

Guidance literature:: With 0,2,4-dichlorophenyl-0-methylisopropylamidothiophosphate; triethylamine; In dichloromethane; at 0 ℃;
DOI:10.1002/ejoc.200300611

Reference yield:

: 332950-54-6
S-tert-butyl 3-[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]propanethioate

: 343969-50-6
(1S,5R,7aS)-7a-methyl-4-phenylthio-1-{(1S)-2-[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]-1-(tosyloxymethyl)ethyl}-2,3,5,6,7,7a-hexahydro-1H-inden-5-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 95 percent / LDA / tetrahydrofuran; hexane

2.1: TrSbCl₆ / CH₂Cl₂ / 2 h / -78 °C

2.2: 79 percent / KOH / methanol / 1 h / 20 °C

3.1: 66 percent / CeCl₃*7H₂O; NaBH₄ / methanol; tetrahydrofuran / 2 h / -78 °C

4.1: 100 percent / LiAlH₄ / tetrahydrofuran / 3 h / Heating

5.1: 78 percent / Et₃N; DMPA / CH₂Cl₂ / 0 °C

With sodium tetrahydroborate; lithium aluminium tetrahydride; cerium(III) chloride; 0,2,4-dichlorophenyl-0-methylisopropylamidothiophosphate; triethylamine; lithium diisopropyl amide; triphenylmethylium hexachloroantimonate(V); In tetrahydrofuran; methanol; hexane; dichloromethane;
DOI:10.1002/ejoc.200300611

Reference yield:

: (1E/Z)-1-(tert-butylthio)-3-[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]-1-(trimethylsilyloxy)prop-1-ene

: 343969-50-6
(1S,5R,7aS)-7a-methyl-4-phenylthio-1-{(1S)-2-[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]-1-(tosyloxymethyl)ethyl}-2,3,5,6,7,7a-hexahydro-1H-inden-5-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: TrSbCl₆ / CH₂Cl₂ / 2 h / -78 °C

1.2: 79 percent / KOH / methanol / 1 h / 20 °C

2.1: 66 percent / CeCl₃*7H₂O; NaBH₄ / methanol; tetrahydrofuran / 2 h / -78 °C

3.1: 100 percent / LiAlH₄ / tetrahydrofuran / 3 h / Heating

4.1: 78 percent / Et₃N; DMPA / CH₂Cl₂ / 0 °C

With sodium tetrahydroborate; lithium aluminium tetrahydride; cerium(III) chloride; 0,2,4-dichlorophenyl-0-methylisopropylamidothiophosphate; triethylamine; triphenylmethylium hexachloroantimonate(V); In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1002/ejoc.200300611