tert-Butyl-[(1R,4S,5S,6S,7R,8S)-4-isopropyl-8-(4-methoxy-benzyloxymethyl)-1,7-dimethyl-bicyclo[3.2.1]oct-6-ylmethoxy]-dimethyl-silane

Base Information

Chemical Name:tert-Butyl-[(1R,4S,5S,6S,7R,8S)-4-isopropyl-8-(4-methoxy-benzyloxymethyl)-1,7-dimethyl-bicyclo[3.2.1]oct-6-ylmethoxy]-dimethyl-silane
CAS No.:138366-27-5
Molecular Formula:C₂₉H₅₀O₃Si
Molecular Weight:474.8
Hs Code.:

Synonyms:tert-Butyl-[(1R,4S,5S,6S,7R,8S)-4-isopropyl-8-(4-methoxy-benzyloxymethyl)-1,7-dimethyl-bicyclo[3.2.1]oct-6-ylmethoxy]-dimethyl-silane

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Chemical Property of tert-Butyl-[(1R,4S,5S,6S,7R,8S)-4-isopropyl-8-(4-methoxy-benzyloxymethyl)-1,7-dimethyl-bicyclo[3.2.1]oct-6-ylmethoxy]-dimethyl-silane

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Technology Process of tert-Butyl-[(1R,4S,5S,6S,7R,8S)-4-isopropyl-8-(4-methoxy-benzyloxymethyl)-1,7-dimethyl-bicyclo[3.2.1]oct-6-ylmethoxy]-dimethyl-silane

There total 13 articles about tert-Butyl-[(1R,4S,5S,6S,7R,8S)-4-isopropyl-8-(4-methoxy-benzyloxymethyl)-1,7-dimethyl-bicyclo[3.2.1]oct-6-ylmethoxy]-dimethyl-silane 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: 90.0%

: 138366-26-4
[(1R,4S,5S,6S,7R,8S)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-4-isopropyl-1,7-dimethyl-bicyclo[3.2.1]oct-8-yl]-methanol

: 824-94-2
p-methoxybenzyl chloride

: 138366-27-5
tert-Butyl-[(1R,4S,5S,6S,7R,8S)-4-isopropyl-8-(4-methoxy-benzyloxymethyl)-1,7-dimethyl-bicyclo[3.2.1]oct-6-ylmethoxy]-dimethyl-silane

Guidance literature:: With potassium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 23 ℃;
DOI:10.1016/S0040-4039(00)93591-3

Reference yield:

: (1R,5R,6R,7R,8S)-8-Benzyloxy-7-hydroxymethyl-5,6-dimethyl-bicyclo[3.2.1]octan-2-ol

: 138366-27-5
tert-Butyl-[(1R,4S,5S,6S,7R,8S)-4-isopropyl-8-(4-methoxy-benzyloxymethyl)-1,7-dimethyl-bicyclo[3.2.1]oct-6-ylmethoxy]-dimethyl-silane

Guidance literature:: Multi-step reaction with 9 steps

1: 95 percent / imidazole / dimethylformamide / 24 °C

2: 75 percent / Swern oxidation

3: 77 percent / tetrahydrofuran / -78 - 0 °C

4: 85 percent / KH / tetrahydrofuran; dimethylformamide / ultrasonication

5: 1) Li, liquid NH₃, 2) H₂ / 2) 10percent Pd/C / 1) EtOH/THF, -34 degC, 2) AcOEt, r.t.

6: 98 percent / pyridinium chlorochromate / CH₂Cl₂ / 25 °C

7: 99 percent / KH / tetrahydrofuran / 25 °C

8: 1) BF₃*OEt₂, 2) diisobutylaluminium hydride / 1) CH₂Cl₂/hexane, -78 degC, 10 min, 2) -30 degC

9: 90 percent / KH / tetrahydrofuran; dimethylformamide / 23 °C

With 1H-imidazole; boron trifluoride diethyl etherate; ammonia; hydrogen; lithium; potassium hydride; diisobutylaluminium hydride; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)93591-3

Reference yield:

: 138366-21-9
(1S,2S,5R,6R,7R,8S)-8-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxymethyl)-2-isopropenyl-5,6-dimethyl-bicyclo[3.2.1]octan-2-ol

: 138366-27-5
tert-Butyl-[(1R,4S,5S,6S,7R,8S)-4-isopropyl-8-(4-methoxy-benzyloxymethyl)-1,7-dimethyl-bicyclo[3.2.1]oct-6-ylmethoxy]-dimethyl-silane

Guidance literature:: Multi-step reaction with 6 steps

1: 85 percent / KH / tetrahydrofuran; dimethylformamide / ultrasonication

2: 1) Li, liquid NH₃, 2) H₂ / 2) 10percent Pd/C / 1) EtOH/THF, -34 degC, 2) AcOEt, r.t.

3: 98 percent / pyridinium chlorochromate / CH₂Cl₂ / 25 °C

4: 99 percent / KH / tetrahydrofuran / 25 °C

5: 1) BF₃*OEt₂, 2) diisobutylaluminium hydride / 1) CH₂Cl₂/hexane, -78 degC, 10 min, 2) -30 degC

6: 90 percent / KH / tetrahydrofuran; dimethylformamide / 23 °C

With boron trifluoride diethyl etherate; ammonia; hydrogen; lithium; potassium hydride; diisobutylaluminium hydride; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)93591-3