(1S,2S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-2-p-tolyl-cyclopentanecarboxylic acid ethyl ester

Base Information

• Chemical Name: (1S,2S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-2-p-tolyl-cyclopentanecarboxylic acid ethyl ester
• CAS No.: 740800-43-5
• Molecular Formula: C₂₂H₃₆O₃Si
• Molecular Weight: 376.612
• Mol file: 740800-43-5.mol

Synonyms:(1S,2S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-2-p-tolyl-cyclopentanecarboxylic acid ethyl ester

Chemical Property of (1S,2S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-2-p-tolyl-cyclopentanecarboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-2-p-tolyl-cyclopentanecarboxylic acid ethyl ester

There total 1 articles about (1S,2S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-2-p-tolyl-cyclopentanecarboxylic acid ethyl ester 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: 100.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (+)-(1S,2S,4R)-4-hydroxy-2-methyl-2-p-tolylcyclopentanecarboxylic acid ethyl ester (613669-95-7) → (1S,2S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-2-p-tolyl-cyclopentanecarboxylic acid ethyl ester (740800-43-5)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

DOI:10.1016/j.tet.2004.05.037

Reference yield: 93.0%

methyl iodide (74-88-4) + (1S,2S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-2-p-tolyl-cyclopentanecarboxylic acid ethyl ester (740800-43-5) → (1R,2R,4S)-4-(tert-butyl-dimethyl-silanyloxy)-1,2-dimethyl-2-p-tolyl-cyclopentanecarboxylic acid ethyl ester (740800-44-6)

Guidance literature:

(1S,2S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-2-p-tolyl-cyclopentanecarboxylic acid ethyl ester; With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; at -90 ℃; for 0.666667h;

methyl iodide; In tetrahydrofuran; diethyl ether; hexane; at -90 - 0 ℃; Further stages.;

DOI:10.1016/j.tet.2004.05.037

Reference yield:

(1S,2S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-2-p-tolyl-cyclopentanecarboxylic acid ethyl ester (740800-43-5) → [(1R,2R)-1,2-Dimethyl-2-(4-methyl-cyclohexa-2,5-dienyl)-cyclopentyl]-methanol

Guidance literature:

Multi-step reaction with 6 steps

1.1: LDA; HMPA / tetrahydrofuran; diethyl ether; hexane / 0.67 h / -90 °C

1.2: 93 percent / tetrahydrofuran; diethyl ether; hexane / -90 - 0 °C

2.1: 98 percent / TBAF / tetrahydrofuran / 4 h / 20 °C

3.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

3.2: 98 percent / tetrahydrofuran / 1 h

4.1: 96 percent / AIBN; Bu₃SnH / toluene / 0.67 h / Heating

5.1: 98 percent / LiAlH₄ / diethyl ether / 0 - 20 °C

6.1: Li; liquid NH₃ / 2-methyl-propan-2-ol

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; ammonia; tri-n-butyl-tin hydride; lithium; sodium hydride; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; toluene; tert-butyl alcohol; 6.1: Birch reduction;

DOI:10.1016/j.tet.2004.05.037

upstream raw materials:

tert-butyldimethylsilyl chloride

(+)-(1S,2S,4R)-4-hydroxy-2-methyl-2-p-tolylcyclopentanecarboxylic acid ethyl ester

Downstream raw materials:

(1R,2R,4S)-4-(tert-butyl-dimethyl-silanyloxy)-1,2-dimethyl-2-p-tolyl-cyclopentanecarboxylic acid ethyl ester

(1R,2R)-(1,2-dimethyl-2-p-tolyl-cyclopentyl)methanol

(1R,2R,4S)-1,2-dimethyl-2-p-tolylcyclopentanecarboxylic acid ethyl ester

(1R,2R,4S)-4-hydroxy-1,2-dimethyl-2-p-tolyl-cyclopentanecarboxylic acid ethyl ester