(1S,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(6-methoxy-pyridin-3-yl)-cyclohex-2-enol

Base Information

Chemical Name:(1S,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(6-methoxy-pyridin-3-yl)-cyclohex-2-enol
CAS No.:249552-12-3
Molecular Formula:C₁₈H₂₉NO₃Si
Molecular Weight:335.519
Hs Code.:

Synonyms:(1S,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(6-methoxy-pyridin-3-yl)-cyclohex-2-enol

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Chemical Property of (1S,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(6-methoxy-pyridin-3-yl)-cyclohex-2-enol

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Technology Process of (1S,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(6-methoxy-pyridin-3-yl)-cyclohex-2-enol

There total 6 articles about (1S,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(6-methoxy-pyridin-3-yl)-cyclohex-2-enol 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: 73.0%

: 249552-10-1
(1R,4S,4aR,5S,7R,8S,8aS)-8-(tert-Butyl-dimethyl-silanyloxy)-7-(6-methoxy-pyridin-3-yl)-1,4,4a,5,6,7,8,8a-octahydro-1,4-methano-naphthalen-5-ol

: 249552-12-3
(1S,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(6-methoxy-pyridin-3-yl)-cyclohex-2-enol

Guidance literature:: With sodium hydrogencarbonate; In diphenylether; at 280 ℃; for 0.5h;

Reference yield:

: 146830-36-6
(+)-(1S,4R,4aS,5R,8S,8aR)-5-Acetoxy-1,4,4a,5,8,8a-hexahydro-8-hydroxy-endo-1,4-methanonaphthalene

: 249552-12-3
(1S,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(6-methoxy-pyridin-3-yl)-cyclohex-2-enol

Guidance literature:: Multi-step reaction with 6 steps

1: 95 percent / PDC / CH₂Cl₂

2: 93 percent / lipase PS (Pseudomonas sp., Amano); phosphate buffer / 21 h / 20 °C / pH 7.6

3: 98 percent / imidazole / dimethylformamide

4: 64 percent / lithium 2-thienylcyanocuprate; BF₃*Et₂O / tetrahydrofuran; diethyl ether / -78 °C

5: 83 percent / NaBH₄ / methanol

6: 73 percent / NaHCO₃ / diphenyl ether / 0.5 h / 280 °C

With 1H-imidazole; sodium tetrahydroborate; dipyridinium dichromate; phosphate buffer; lipase PS (Pseudomonas sp., Amano); boron trifluoride diethyl etherate; sodium hydrogencarbonate; thien-2-yl(cyano)copper lithium; In tetrahydrofuran; methanol; diphenylether; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1: Oxidation / 2: Deacetylation / 3: Substitution / 4: Addition / 5: Reduction / 6: Elimination;

Reference yield:

: 148903-03-1
(-)-(1S,4R,4aS,5S,8aS)-5-acetoxy-1,4,4a,8a-tetrahydro-endo-1,4-methanonaphthalen-8(5H)-one

: 249552-12-3
(1S,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(6-methoxy-pyridin-3-yl)-cyclohex-2-enol

Guidance literature:: Multi-step reaction with 5 steps

1: 93 percent / lipase PS (Pseudomonas sp., Amano); phosphate buffer / 21 h / 20 °C / pH 7.6

2: 98 percent / imidazole / dimethylformamide

3: 64 percent / lithium 2-thienylcyanocuprate; BF₃*Et₂O / tetrahydrofuran; diethyl ether / -78 °C

4: 83 percent / NaBH₄ / methanol

5: 73 percent / NaHCO₃ / diphenyl ether / 0.5 h / 280 °C

With 1H-imidazole; sodium tetrahydroborate; phosphate buffer; lipase PS (Pseudomonas sp., Amano); boron trifluoride diethyl etherate; sodium hydrogencarbonate; thien-2-yl(cyano)copper lithium; In tetrahydrofuran; methanol; diphenylether; diethyl ether; N,N-dimethyl-formamide; 1: Deacetylation / 2: Substitution / 3: Addition / 4: Reduction / 5: Elimination;