(1S,3S,4S,7S)-7-((1R,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}cyclopropyl)-4-hydroxy-1,3-dimethyl-2-oxooctyl benzoate

Base Information

Chemical Name:(1S,3S,4S,7S)-7-((1R,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}cyclopropyl)-4-hydroxy-1,3-dimethyl-2-oxooctyl benzoate
CAS No.:460997-48-2
Molecular Formula:C₃₇H₄₈O₅Si
Molecular Weight:600.871
Hs Code.:

Synonyms:(1S,3S,4S,7S)-7-((1R,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}cyclopropyl)-4-hydroxy-1,3-dimethyl-2-oxooctyl benzoate

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Chemical Property of (1S,3S,4S,7S)-7-((1R,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}cyclopropyl)-4-hydroxy-1,3-dimethyl-2-oxooctyl benzoate

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Technology Process of (1S,3S,4S,7S)-7-((1R,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}cyclopropyl)-4-hydroxy-1,3-dimethyl-2-oxooctyl benzoate

There total 9 articles about (1S,3S,4S,7S)-7-((1R,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}cyclopropyl)-4-hydroxy-1,3-dimethyl-2-oxooctyl benzoate 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: 83.0%

: 460997-47-1
(-)-(R)-3-oxopentan-2-yl benzoate

: 460997-46-0
(4S)-4-((1R,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}cyclopropyl)pentanal

: 460997-48-2
(1S,3S,4S,7S)-7-((1R,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}cyclopropyl)-4-hydroxy-1,3-dimethyl-2-oxooctyl benzoate

Guidance literature:: (-)-(R)-3-oxopentan-2-yl benzoate; With N,N-dimethyl-ethanamine; dicyclohexylboron chloride; In diethyl ether; at 0 ℃;

(4S)-4-((1R,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}cyclopropyl)pentanal; In diethyl ether; at -78 - -23 ℃; for 14h;

With pH 7 buffer; dihydrogen peroxide; In methanol; pH=7;
DOI:10.1002/1521-3773(20020617)41:12<2144::AID-ANIE2144>3.0.CO;2-E

Reference yield:

: 334705-97-4
(1S,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-1-isopropenylcyclopropane

: 460997-48-2
(1S,3S,4S,7S)-7-((1R,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}cyclopropyl)-4-hydroxy-1,3-dimethyl-2-oxooctyl benzoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: BH₃*THF / tetrahydrofuran / 2.5 h / -30 - 20 °C

1.2: 91 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 3 h / 20 °C

2.1: PCC / CH₂Cl₂ / 1.5 h / 20 °C

3.1: 10.7 g / NaH / tetrahydrofuran / 1 h / 20 °C

4.1: 97 percent / H₂ / PtO₂ / ethyl acetate / 6 h

5.1: 97 percent / Dibal-H / toluene; hexane / 1 h / -78 °C

6.1: (c-Hex)2BCl; EtNMe₂ / diethyl ether / 2 h / 0 °C

6.2: diethyl ether / 20 h / -78 - -23 °C

6.3: 83 percent / phosphate buffer; aq. H₂O₂ / diethyl ether; methanol / 1 h / 0 °C

With borane-THF; N,N-dimethyl-ethanamine; dicyclohexylboron chloride; hydrogen; sodium hydride; diisobutylaluminium hydride; pyridinium chlorochromate; platinum(IV) oxide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethyl acetate; toluene; 3.1: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jo0496042

Reference yield:

: 460997-43-7
(2R)-2-((1R,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}cyclopropyl)propan-1-ol

: 460997-48-2
(1S,3S,4S,7S)-7-((1R,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}cyclopropyl)-4-hydroxy-1,3-dimethyl-2-oxooctyl benzoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: PCC / CH₂Cl₂ / 1.5 h / 20 °C

2.1: 10.7 g / NaH / tetrahydrofuran / 1 h / 20 °C

3.1: 97 percent / H₂ / PtO₂ / ethyl acetate / 6 h

4.1: 97 percent / Dibal-H / toluene; hexane / 1 h / -78 °C

5.1: (c-Hex)2BCl; EtNMe₂ / diethyl ether / 2 h / 0 °C

5.2: diethyl ether / 20 h / -78 - -23 °C

5.3: 83 percent / phosphate buffer; aq. H₂O₂ / diethyl ether; methanol / 1 h / 0 °C

With N,N-dimethyl-ethanamine; dicyclohexylboron chloride; hydrogen; sodium hydride; diisobutylaluminium hydride; pyridinium chlorochromate; platinum(IV) oxide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethyl acetate; toluene; 2.1: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jo0496042