(-)-(3aS,4S,5R,6aR)-5-hydroxy-4-{4-[(S)-1'-(tert-butyldimethylsilanyloxy)hexyl]phenyl}-5-[tert-butyldimethylsilanyloxy]hexahydropentalen-2-one

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Chemical Name:(-)-(3aS,4S,5R,6aR)-5-hydroxy-4-{4-[(S)-1'-(tert-butyldimethylsilanyloxy)hexyl]phenyl}-5-[tert-butyldimethylsilanyloxy]hexahydropentalen-2-one
CAS No.:431041-25-7
Molecular Formula:C₃₂H₅₆O₃Si₂
Molecular Weight:544.966
Hs Code.:

Synonyms:(-)-(3aS,4S,5R,6aR)-5-hydroxy-4-{4-[(S)-1'-(tert-butyldimethylsilanyloxy)hexyl]phenyl}-5-[tert-butyldimethylsilanyloxy]hexahydropentalen-2-one

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Chemical Property of (-)-(3aS,4S,5R,6aR)-5-hydroxy-4-{4-[(S)-1'-(tert-butyldimethylsilanyloxy)hexyl]phenyl}-5-[tert-butyldimethylsilanyloxy]hexahydropentalen-2-one

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Technology Process of (-)-(3aS,4S,5R,6aR)-5-hydroxy-4-{4-[(S)-1'-(tert-butyldimethylsilanyloxy)hexyl]phenyl}-5-[tert-butyldimethylsilanyloxy]hexahydropentalen-2-one

There total 14 articles about (-)-(3aS,4S,5R,6aR)-5-hydroxy-4-{4-[(S)-1'-(tert-butyldimethylsilanyloxy)hexyl]phenyl}-5-[tert-butyldimethylsilanyloxy]hexahydropentalen-2-one 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:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 431041-23-5
(+)-(3'aS,4'S,5'R,6'aR)-[4'-[4-((S)-1''-(tert-butyldimethylsilanyloxy)hexyl)phenyl]-1',6'a,6',3'a-tetrahydro-5,5-dimethylspiro[1,3-dioxane-2,2']]pentalen-5'-ol

: 431041-25-7
(-)-(3aS,4S,5R,6aR)-5-hydroxy-4-{4-[(S)-1'-(tert-butyldimethylsilanyloxy)hexyl]phenyl}-5-[tert-butyldimethylsilanyloxy]hexahydropentalen-2-one

Guidance literature:: (+)-(3'aS,4'S,5'R,6'aR)-[4'-[4-((S)-1''-(tert-butyldimethylsilanyloxy)hexyl)phenyl]-1',6'a,6',3'a-tetrahydro-5,5-dimethylspiro[1,3-dioxane-2,2']]pentalen-5'-ol; With water; toluene-4-sulfonic acid; In acetone; at 20 ℃; for 12h;

tert-butyldimethylsilyl chloride; With 1H-imidazole; In N,N-dimethyl-formamide; at 50 ℃; for 2h; Further stages.;
DOI:10.1021/ja0125772

Reference yield:

: 112755-94-9,92007-37-9
(3a'R,6a'S)-5,5-dimethyltetrahydro-1'H-spiro[1,3-dioxane-2,2'-pentalen]-5'(3'H)-one

: 431041-25-7
(-)-(3aS,4S,5R,6aR)-5-hydroxy-4-{4-[(S)-1'-(tert-butyldimethylsilanyloxy)hexyl]phenyl}-5-[tert-butyldimethylsilanyloxy]hexahydropentalen-2-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: lithium (R,R)-bis(phenylethyl)amide; LiCl / tetrahydrofuran; hexane / 0.67 h / -100 °C

1.2: tetrahydrofuran; hexane / 0.5 h / -100 °C

2.1: NCS / CH₂Cl₂ / 1 h / 20 °C

2.2: aq. AcOH / tetrahydrofuran / 2 h / 20 °C

3.1: diethyl ether / 48 h / 0 °C

4.1: aq. NaHCO₃ / diethyl ether / 0.05 h / 20 °C

5.1: t-BuLi / pentane; diethyl ether / 0.5 h / -78 °C

5.2: [(n-Bu₃P)CuI]4 / pentane; diethyl ether / 0.67 h / -10 °C

5.3: 80 percent / pentane; diethyl ether; tetrahydrofuran / 0.5 h / -60 °C

6.1: benzeneseleninic anhydride / tetrahydrofuran / 1 h / 20 °C

7.1: 515 mg / NaBH₄ / ethanol / 7 h / -40 °C

8.1: p-TsOH; water / acetone / 12 h / 20 °C

8.2: 423 mg / imidazole / dimethylformamide / 2 h / 50 °C

With sodium tetrahydroborate; N-chloro-succinimide; benzeneseleninic anhydride; water; tert.-butyl lithium; sodium hydrogencarbonate; lithium [R(R*,R*)]-(+)-bis(α-methylbenzyl)amide; toluene-4-sulfonic acid; lithium chloride; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; acetone; pentane;
DOI:10.1021/ja0125772

Reference yield:

: 873949-36-1
(-)-(3'aS-cis)-N-[3',3'a,4',6'a-tetrahydro-5,5-dimethylspiro[1,3-dioxane-2,2'(1'H)-pentalen-5'-yl]]-N'-(p-toluenesulfonyl)diazene

: 431041-25-7
(-)-(3aS,4S,5R,6aR)-5-hydroxy-4-{4-[(S)-1'-(tert-butyldimethylsilanyloxy)hexyl]phenyl}-5-[tert-butyldimethylsilanyloxy]hexahydropentalen-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: t-BuLi / pentane; diethyl ether / 0.5 h / -78 °C

1.2: [(n-Bu₃P)CuI]4 / pentane; diethyl ether / 0.67 h / -10 °C

1.3: 80 percent / pentane; diethyl ether; tetrahydrofuran / 0.5 h / -60 °C

2.1: benzeneseleninic anhydride / tetrahydrofuran / 1 h / 20 °C

3.1: 515 mg / NaBH₄ / ethanol / 7 h / -40 °C

4.1: p-TsOH; water / acetone / 12 h / 20 °C

4.2: 423 mg / imidazole / dimethylformamide / 2 h / 50 °C

With sodium tetrahydroborate; benzeneseleninic anhydride; water; tert.-butyl lithium; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; ethanol; acetone; pentane;
DOI:10.1021/ja0125772