(+)-(2R,5E,6S,8S,9S,11S)-11-<(tert-butyldiphenylsilyloxy)methyl>-9-methyl-2-phenyl-5-<2-(phenylsulphonyl)ethylidene>-1,3-dioxaspiro<5.5>undecan-8-ol

Base Information

Chemical Name:(+)-(2R,5E,6S,8S,9S,11S)-11-<(tert-butyldiphenylsilyloxy)methyl>-9-methyl-2-phenyl-5-<2-(phenylsulphonyl)ethylidene>-1,3-dioxaspiro<5.5>undecan-8-ol
CAS No.:127785-58-4
Molecular Formula:C₄₁H₄₈O₆SSi
Molecular Weight:696.98
Hs Code.:

Synonyms:(+)-(2R,5E,6S,8S,9S,11S)-11-<(tert-butyldiphenylsilyloxy)methyl>-9-methyl-2-phenyl-5-<2-(phenylsulphonyl)ethylidene>-1,3-dioxaspiro<5.5>undecan-8-ol

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Chemical Property of (+)-(2R,5E,6S,8S,9S,11S)-11-<(tert-butyldiphenylsilyloxy)methyl>-9-methyl-2-phenyl-5-<2-(phenylsulphonyl)ethylidene>-1,3-dioxaspiro<5.5>undecan-8-ol

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Technology Process of (+)-(2R,5E,6S,8S,9S,11S)-11-<(tert-butyldiphenylsilyloxy)methyl>-9-methyl-2-phenyl-5-<2-(phenylsulphonyl)ethylidene>-1,3-dioxaspiro<5.5>undecan-8-ol

There total 18 articles about (+)-(2R,5E,6S,8S,9S,11S)-11-<(tert-butyldiphenylsilyloxy)methyl>-9-methyl-2-phenyl-5-<2-(phenylsulphonyl)ethylidene>-1,3-dioxaspiro<5.5>undecan-8-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: 84.0%

: 115031-05-5
(+)-<2R,4E,6(2R,4S,6S,8R,9S)>-6-(4-benzoyloxy-8,9-dimethyl-1,7-dioxaspiro<5.5>undecan-2-yl)-2,4-dimethyl-4-hexenal

: 115030-97-2,124600-50-6
(+)-(2R,5S(E),6S,8S,9S,11S)-11-<(tert-butyldiphenylsilyloxy)methyl>-9-methyl-2-phenyl-5-<2-(phenylsulphonyl)ethenyl>-1,3-dioxaspiro<5.5>undecan-8-ol

: 127785-58-4
(+)-(2R,5E,6S,8S,9S,11S)-11-<(tert-butyldiphenylsilyloxy)methyl>-9-methyl-2-phenyl-5-<2-(phenylsulphonyl)ethylidene>-1,3-dioxaspiro<5.5>undecan-8-ol

: 124553-35-1
C₆₇H₈₄O₁₁SSi

Guidance literature:: With tert.-butyl lithium; In tetrahydrofuran; at -78 ℃; for 1h; 1.) -78 deg C, 10 min;
DOI:10.1016/S0040-4020(01)89182-1

Reference yield:

: 127785-52-8
2-bromo-4-phenylthiobut-1-ene

: 127785-58-4
(+)-(2R,5E,6S,8S,9S,11S)-11-<(tert-butyldiphenylsilyloxy)methyl>-9-methyl-2-phenyl-5-<2-(phenylsulphonyl)ethylidene>-1,3-dioxaspiro<5.5>undecan-8-ol

Guidance literature:: Multi-step reaction with 7 steps

1: 87 percent / tert-butyl-lithium / diethyl ether; tetrahydrofuran / 1 h / -78 °C

2: 1.) mCPBA; 2.) oxone / 1.) CH₂Cl₂, 0 deg C, 10 min; 2.) methanol/THF/H₂O, 0 deg C, 5 h

3: 1.) BH₃*DMS; 2.) aq. NaOH, H₂O₂ / 1.) THF, 0 deg C, --> room temp., 16 h; 2.) H₂O, 30 min

4: 45 percent / pyridinium-p-toluene sulphonate / benzene / 1 h / Heating; Dean-Stark conditions

5: 1.) n-butyllithium / 1.) hexanes, THF, -78 deg C, 15 min; 2.) -78 deg C, 1 h

6: 99 percent / mCPBA, sat. sodium hydrogencarbonate / CH₂Cl₂ / 0.75 h / 10 °C

7: 16 percent / 1.) tert-butyllithium / tetrahydrofuran / 1 h / -78 °C / 1.) -78 deg C, 10 min

With Oxone; sodium hydroxide; n-butyllithium; dimethylsulfide borane complex; dihydrogen peroxide; tert.-butyl lithium; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; diethyl ether; dichloromethane; benzene;
DOI:10.1016/S0040-4020(01)89182-1

Reference yield:

: 116511-47-8
(-)-(2S,4S,5S)-2-<(tert-butyldiphenylsilyloxy)methyl>-5-hydroxy-4-methylcyclohexanone

: 127785-58-4
(+)-(2R,5E,6S,8S,9S,11S)-11-<(tert-butyldiphenylsilyloxy)methyl>-9-methyl-2-phenyl-5-<2-(phenylsulphonyl)ethylidene>-1,3-dioxaspiro<5.5>undecan-8-ol

Guidance literature:: Multi-step reaction with 7 steps

1: 87 percent / tert-butyl-lithium / diethyl ether; tetrahydrofuran / 1 h / -78 °C

2: 1.) mCPBA; 2.) oxone / 1.) CH₂Cl₂, 0 deg C, 10 min; 2.) methanol/THF/H₂O, 0 deg C, 5 h

3: 1.) BH₃*DMS; 2.) aq. NaOH, H₂O₂ / 1.) THF, 0 deg C, --> room temp., 16 h; 2.) H₂O, 30 min

4: 45 percent / pyridinium-p-toluene sulphonate / benzene / 1 h / Heating; Dean-Stark conditions

5: 1.) n-butyllithium / 1.) hexanes, THF, -78 deg C, 15 min; 2.) -78 deg C, 1 h

6: 99 percent / mCPBA, sat. sodium hydrogencarbonate / CH₂Cl₂ / 0.75 h / 10 °C

7: 16 percent / 1.) tert-butyllithium / tetrahydrofuran / 1 h / -78 °C / 1.) -78 deg C, 10 min

With Oxone; sodium hydroxide; n-butyllithium; dimethylsulfide borane complex; dihydrogen peroxide; tert.-butyl lithium; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; diethyl ether; dichloromethane; benzene;
DOI:10.1016/S0040-4020(01)89182-1