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

Base Information

• Chemical Name: [(1S,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-isopropenyl-2-methyl-cyclopentyl]-methanol
• CAS No.: 950849-05-5
• Molecular Formula: C₂₆H₃₆O₂Si
• Molecular Weight: 408.656
• Mol file: 950849-05-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about [(1S,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-isopropenyl-2-methyl-cyclopentyl]-methanol 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: 99.0%

(1S,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-isopropenyl-2-methyl-cyclopentanecarboxylic acid methyl ester (663605-85-4) → [(1S,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-isopropenyl-2-methyl-cyclopentyl]-methanol (950849-05-5)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1002/chem.200700302

Reference yield:

(S)-p-mentha-6,8-dien-2-one (2244-16-8,6485-40-1) → [(1S,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-isopropenyl-2-methyl-cyclopentyl]-methanol (950849-05-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: dihydrogen peroxide; sodium hydroxide

2.1: lithium chloride; trifluoroacetic acid / Inert atmosphere

3.1: toluene-4-sulfonic acid / Inert atmosphere

4.1: methanol / Inert atmosphere; Cooling with ice

5.1: toluene-4-sulfonic acid / methanol / Inert atmosphere

5.2: Inert atmosphere

6.1: lithium aluminium tetrahydride / tetrahydrofuran / Inert atmosphere

With lithium aluminium tetrahydride; dihydrogen peroxide; toluene-4-sulfonic acid; trifluoroacetic acid; lithium chloride; sodium hydroxide; In tetrahydrofuran; methanol;

DOI:10.1007/s12039-016-1197-7

Reference yield:

(2R,3S,5S)-2-Chloro-3-hydroxy-5-isopropenyl-2-methyl-cyclohexanone (156714-47-5) → [(1S,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-isopropenyl-2-methyl-cyclopentyl]-methanol (950849-05-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: toluene-4-sulfonic acid / Inert atmosphere

2.1: methanol / Inert atmosphere; Cooling with ice

3.1: toluene-4-sulfonic acid / methanol / Inert atmosphere

3.2: Inert atmosphere

4.1: lithium aluminium tetrahydride / tetrahydrofuran / Inert atmosphere

With lithium aluminium tetrahydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol;

DOI:10.1007/s12039-016-1197-7

upstream raw materials:

(1S,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-isopropenyl-2-methyl-cyclopentanecarboxylic acid methyl ester

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

(S)-carvone oxide

(2R,3S,5S)-2-Chloro-3-hydroxy-5-isopropenyl-2-methyl-cyclohexanone

Downstream raw materials:

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

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

(1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-1-methoxymethoxy-1-methyl-but-3-enyl)-2-methyl-cyclopentanecarbaldehyde

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