tert-Butyl-[(1S,2R,3S,4S)-4-isopropenyl-3-(4-methoxy-benzyloxymethyl)-2-methyl-cyclopentyloxy]-diphenyl-silane

Base Information

• Chemical Name: tert-Butyl-[(1S,2R,3S,4S)-4-isopropenyl-3-(4-methoxy-benzyloxymethyl)-2-methyl-cyclopentyloxy]-diphenyl-silane
• CAS No.: 663605-86-5
• Molecular Formula: C₃₄H₄₄O₃Si
• Molecular Weight: 528.807

Synonyms:tert-Butyl-[(1S,2R,3S,4S)-4-isopropenyl-3-(4-methoxy-benzyloxymethyl)-2-methyl-cyclopentyloxy]-diphenyl-silane

Chemical Property of tert-Butyl-[(1S,2R,3S,4S)-4-isopropenyl-3-(4-methoxy-benzyloxymethyl)-2-methyl-cyclopentyloxy]-diphenyl-silane

Chemical Property:

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Technology Process of tert-Butyl-[(1S,2R,3S,4S)-4-isopropenyl-3-(4-methoxy-benzyloxymethyl)-2-methyl-cyclopentyloxy]-diphenyl-silane

There total 11 articles about tert-Butyl-[(1S,2R,3S,4S)-4-isopropenyl-3-(4-methoxy-benzyloxymethyl)-2-methyl-cyclopentyloxy]-diphenyl-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: 82.0%

p-methoxybenzyl chloride (824-94-2) + [(1S,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-isopropenyl-2-methyl-cyclopentyl]-methanol (950849-05-5) → tert-Butyl-[(1S,2R,3S,4S)-4-isopropenyl-3-(4-methoxy-benzyloxymethyl)-2-methyl-cyclopentyloxy]-diphenyl-silane (663605-86-5)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 15h;

DOI:10.1002/chem.200700302

Reference yield:

(S)-p-mentha-6,8-dien-2-one (2244-16-8,6485-40-1) → tert-Butyl-[(1S,2R,3S,4S)-4-isopropenyl-3-(4-methoxy-benzyloxymethyl)-2-methyl-cyclopentyloxy]-diphenyl-silane (663605-86-5)

Guidance literature:

Multi-step reaction with 8 steps

1: sodium hydroxide; dihydrogen peroxide / methanol / 3 h / 20 °C

2: trifluoroacetic acid; lithium chloride / tetrahydrofuran / 1.5 h / 0 °C

3: pyridinium p-toluenesulfonate / dichloromethane / 17 h / 20 °C

4: methanol; diethyl ether / 1 h / 0 °C

5: pyridinium p-toluenesulfonate / methanol / 15 h / 50 °C

6: 1H-imidazole; dmap / N,N-dimethyl-formamide / 20 °C

7: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C

8: sodium hydride / N,N-dimethyl-formamide / 15 h / 20 °C

With 1H-imidazole; dmap; sodium hydroxide; lithium aluminium tetrahydride; dihydrogen peroxide; pyridinium p-toluenesulfonate; sodium hydride; trifluoroacetic acid; lithium chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 4: Favorskii rearrangement;

DOI:10.1002/chem.200700302

Reference yield:

(2R,3S,5S)-2-Chloro-5-isopropenyl-2-methyl-3-(tetrahydro-pyran-2-yloxy)-cyclohexanone (156629-27-5) → tert-Butyl-[(1S,2R,3S,4S)-4-isopropenyl-3-(4-methoxy-benzyloxymethyl)-2-methyl-cyclopentyloxy]-diphenyl-silane (663605-86-5)

Guidance literature:

Multi-step reaction with 5 steps

1: methanol; diethyl ether / 1 h / 0 °C

2: pyridinium p-toluenesulfonate / methanol / 15 h / 50 °C

3: 1H-imidazole; dmap / N,N-dimethyl-formamide / 20 °C

4: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C

5: sodium hydride / N,N-dimethyl-formamide / 15 h / 20 °C

With 1H-imidazole; dmap; lithium aluminium tetrahydride; pyridinium p-toluenesulfonate; sodium hydride; In tetrahydrofuran; methanol; diethyl ether; N,N-dimethyl-formamide; 1: Favorskii rearrangement;

DOI:10.1002/chem.200700302

upstream raw materials:

p-methoxybenzyl chloride

[(1S,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-isopropenyl-2-methyl-cyclopentyl]-methanol

(S)-p-mentha-6,8-dien-2-one

(S)-carvone oxide

Downstream raw materials:

1-[(1S,2R,3R,4S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxymethyl)-3-methyl-cyclopentyl]-ethanone

Acetic acid (R)-2-[(2S,3R,3aR,4S,5R,6S,8S,8aS)-2-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-6,8-bis-methoxymethoxy-3,8-dimethyl-4-triethylsilanyloxy-decahydro-azulen-5-yl]-2-hydroxy-propyl ester

nortrilobolide

(S)-1-[(1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-1-methoxymethoxy-1-methyl-but-3-enyl)-2-methyl-cyclopentyl]-2-ethoxy-prop-2-en-1-ol

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