(+)-(2S,3S,7E)-2,5,5,8-tetramethyl-2,3-methano-9-(t-butyldiphenylsilyloxy)-7-nonene-1-ol

Base Information

Chemical Name:(+)-(2S,3S,7E)-2,5,5,8-tetramethyl-2,3-methano-9-(t-butyldiphenylsilyloxy)-7-nonene-1-ol
CAS No.:184833-58-7
Molecular Formula:C₃₀H₄₄O₂Si
Molecular Weight:464.764
Hs Code.:

Synonyms:(+)-(2S,3S,7E)-2,5,5,8-tetramethyl-2,3-methano-9-(t-butyldiphenylsilyloxy)-7-nonene-1-ol

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Chemical Property of (+)-(2S,3S,7E)-2,5,5,8-tetramethyl-2,3-methano-9-(t-butyldiphenylsilyloxy)-7-nonene-1-ol

Chemical Property:

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Technology Process of (+)-(2S,3S,7E)-2,5,5,8-tetramethyl-2,3-methano-9-(t-butyldiphenylsilyloxy)-7-nonene-1-ol

There total 9 articles about (+)-(2S,3S,7E)-2,5,5,8-tetramethyl-2,3-methano-9-(t-butyldiphenylsilyloxy)-7-nonene-1-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: 88.0%

: (ICH₂)2Zn dimethoxyethane complex

: 184833-17-8
(2E,7E)-2,5,5,8-tetramethyl-9-(t-butyldiphenylsilyloxy)-2,7-nonadien-1-ol

: (-)-(2R,3R,7E)-2,5,5,8-tetramethyl-2,3-methano-9-(t-butyldiphenylsilyloxy)-7-nonene-1-ol

: 184833-58-7
(+)-(2S,3S,7E)-2,5,5,8-tetramethyl-2,3-methano-9-(t-butyldiphenylsilyloxy)-7-nonene-1-ol

Guidance literature:: With chiral dioxaborolane derivative; In dichloromethane; at 0 ℃; for 2h; Yields of byproduct given. Title compound not separated from byproducts;
DOI:10.1016/0040-4039(96)01798-4

Reference yield:

: 75-11-6
diiodomethane

: 184833-17-8
(2E,7E)-2,5,5,8-tetramethyl-9-(t-butyldiphenylsilyloxy)-2,7-nonadien-1-ol

: (-)-(2R,3R,7E)-2,5,5,8-tetramethyl-2,3-methano-9-(t-butyldiphenylsilyloxy)-7-nonene-1-ol

: 184833-58-7
(+)-(2S,3S,7E)-2,5,5,8-tetramethyl-2,3-methano-9-(t-butyldiphenylsilyloxy)-7-nonene-1-ol

Guidance literature:: diiodomethane; With 1,2-dimethoxyethane; diethylzinc; In dichloromethane; at 0 - 20 ℃; for 0.75h;

(2E,7E)-2,5,5,8-tetramethyl-9-(t-butyldiphenylsilyloxy)-2,7-nonadien-1-ol; With (R,R)-dioxaborolane; In dichloromethane; at 0 - 20 ℃; for 1h; Title compound not separated from byproducts;
DOI:10.1016/S0040-4020(97)01014-4

Reference yield:

: 17804-59-0
diethyl 3,3-dimethylglutarate

: 184833-58-7
(+)-(2S,3S,7E)-2,5,5,8-tetramethyl-2,3-methano-9-(t-butyldiphenylsilyloxy)-7-nonene-1-ol

Guidance literature:: Multi-step reaction with 8 steps

1.1: 82 percent / Na / toluene / 16 h / Heating

2.1: 80 percent / aq. HCl / tetrahydrofuran / 3 h / Heating

3.1: 70 percent / LAH / tetrahydrofuran / 12 h / Heating

4.1: 100 percent / NaIO₄ / tetrahydrofuran; H₂O / 24 h / 20 °C

5.1: 82 percent / benzene / 24 h / Heating

6.1: 85 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 0.5 h / -78 °C

7.1: 66 percent / imidazole / dimethylformamide / 0.75 h / 20 °C

8.1: DME; Et₂Zn / CH₂Cl₂ / 0.75 h / 0 - 20 °C

8.2: (R,R)-dioxaborolane / CH₂Cl₂ / 1 h / 0 - 20 °C

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; 1,2-dimethoxyethane; cerium(III) chloride; diethylzinc; sodium; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene; 1.1: Cyclization / 2.1: Hydrolysis / 3.1: Reduction / 4.1: Oxidation / 5.1: Condensation / 6.1: Luche reduction / 7.1: silylation / 8.1: Metallation / 8.2: Cyclization;
DOI:10.1016/S0040-4020(97)01014-4