(4S,5S,8S,9S,10S,13R,14S,17S)-methyl 4-t-butyldiphenylsilyloxy-1,7-dioxo-17-(3-furyl)-14-hydroxyandrostane-10-carboxylate

Base Information

Chemical Name:(4S,5S,8S,9S,10S,13R,14S,17S)-methyl 4-t-butyldiphenylsilyloxy-1,7-dioxo-17-(3-furyl)-14-hydroxyandrostane-10-carboxylate
CAS No.:448961-29-3
Molecular Formula:C₄₀H₄₈O₇Si
Molecular Weight:668.902
Hs Code.:

Synonyms:(4S,5S,8S,9S,10S,13R,14S,17S)-methyl 4-t-butyldiphenylsilyloxy-1,7-dioxo-17-(3-furyl)-14-hydroxyandrostane-10-carboxylate

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Chemical Property of (4S,5S,8S,9S,10S,13R,14S,17S)-methyl 4-t-butyldiphenylsilyloxy-1,7-dioxo-17-(3-furyl)-14-hydroxyandrostane-10-carboxylate

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Technology Process of (4S,5S,8S,9S,10S,13R,14S,17S)-methyl 4-t-butyldiphenylsilyloxy-1,7-dioxo-17-(3-furyl)-14-hydroxyandrostane-10-carboxylate

There total 5 articles about (4S,5S,8S,9S,10S,13R,14S,17S)-methyl 4-t-butyldiphenylsilyloxy-1,7-dioxo-17-(3-furyl)-14-hydroxyandrostane-10-carboxylate 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: 63.0%

: 448961-06-6
(4S,5S,9R,10R,1'R,5'R)-methyl 8-bromo-4-t-butyldiphenylsilyloxy-1,7-dioxo-9-{2''-[5'-(3-furyl)-1'-methyl-2'-oxocyclopent-1'-yl]-eth-1''-yl}-decahydronaphthalene-10-carboxylate

: 448961-29-3
(4S,5S,8S,9S,10S,13R,14S,17S)-methyl 4-t-butyldiphenylsilyloxy-1,7-dioxo-17-(3-furyl)-14-hydroxyandrostane-10-carboxylate

: 448961-30-6
(4S,5S,8R,9S,10S,13R,14S,17S)-methyl 4-t-butyldiphenylsilyloxy-1,7-dioxo-17-(3-furyl)-14-hydroxyandrostane-10-carboxylate methyl

: (1S,2S,3S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-[(E)-6-((1R,2R)-2-furan-3-yl-1-methyl-5-oxo-cyclopentyl)-2-oxo-hex-3-enyl]-6-oxo-cyclohexanecarboxylic acid methyl ester

Guidance literature:: With samarium diiodide; In tetrahydrofuran; at -20 ℃;
DOI:10.1021/ol027125o

Reference yield: 63.0%

: 448961-06-6
(4S,5S,9R,10R,1'R,5'R)-methyl 8-bromo-4-t-butyldiphenylsilyloxy-1,7-dioxo-9-{2''-[5'-(3-furyl)-1'-methyl-2'-oxocyclopent-1'-yl]-eth-1''-yl}-decahydronaphthalene-10-carboxylate

: methyl 4-t-butyldiphenylsilylsilyloxy-3-{6'-[3''-(3-furyl)-2''-methyl-1''-oxocyclopent-2''-yl]-2'-oxohex-3'-en-1'-yl}-1-oxocyclohexane-2-carboxylate

: 448961-29-3
(4S,5S,8S,9S,10S,13R,14S,17S)-methyl 4-t-butyldiphenylsilyloxy-1,7-dioxo-17-(3-furyl)-14-hydroxyandrostane-10-carboxylate

: 448961-30-6
(4S,5S,8R,9S,10S,13R,14S,17S)-methyl 4-t-butyldiphenylsilyloxy-1,7-dioxo-17-(3-furyl)-14-hydroxyandrostane-10-carboxylate methyl

Guidance literature:: With samarium diiodide; In tetrahydrofuran; at -20 ℃; for 16h;
DOI:10.1021/jo025612b

Reference yield:

: 415928-19-7
(4S)-4-t-butyldiphenylsilyloxy-2-carbomethoxycyclohex-2-en-1-one

: 448961-29-3
(4S,5S,8S,9S,10S,13R,14S,17S)-methyl 4-t-butyldiphenylsilyloxy-1,7-dioxo-17-(3-furyl)-14-hydroxyandrostane-10-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: Cs₂CO₃ / CH₂Cl₂ / 20 °C

2: pTSA / benzene / Heating

3: 63 percent / SmI₂ / tetrahydrofuran / -20 °C

With samarium diiodide; caesium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; benzene;
DOI:10.1021/ol027125o