(1R,3S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-formyl-3-hydroxy-2,2-dimethyl-6-methylene-cyclohexanecarboxylic acid ethyl ester

Base Information

• Chemical Name: (1R,3S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-formyl-3-hydroxy-2,2-dimethyl-6-methylene-cyclohexanecarboxylic acid ethyl ester
• CAS No.: 136611-34-2
• Molecular Formula: C₁₉H₃₄O₅Si
• Molecular Weight: 370.561
• Mol file: 136611-34-2.mol

Synonyms:(1R,3S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-formyl-3-hydroxy-2,2-dimethyl-6-methylene-cyclohexanecarboxylic acid ethyl ester

Chemical Property of (1R,3S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-formyl-3-hydroxy-2,2-dimethyl-6-methylene-cyclohexanecarboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-formyl-3-hydroxy-2,2-dimethyl-6-methylene-cyclohexanecarboxylic acid ethyl ester

There total 1 articles about (1R,3S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-formyl-3-hydroxy-2,2-dimethyl-6-methylene-cyclohexanecarboxylic 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: 90.0%

(1R,3S,5S)-ethyl 5-<(tert-butyldimethylsilyl)oxy>-3-hydroxy-3-hydroxymethyl-2,2-dimethyl-6-methylenecyclohexanecarboxylate (147512-96-7) → (1R,3S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-formyl-3-hydroxy-2,2-dimethyl-6-methylene-cyclohexanecarboxylic acid ethyl ester (136611-34-2)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -60 - 20 ℃; for 1.33333h;

DOI:10.1039/c39930001823

Reference yield:

(1R,3S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-formyl-3-hydroxy-2,2-dimethyl-6-methylene-cyclohexanecarboxylic acid ethyl ester (136611-34-2) → (1R,3S,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-((1R,2R,3S)-3-hydroxy-2-hydroxymethyl-2-methyl-6-methylene-cyclohexylmethyl)-8,8-dimethyl-2-methylene-6-oxa-bicyclo[3.2.1]octan-7-one

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) NaH / 1.) 1,2-dimethoxyethane, 0 deg C, 20 min, 2.) 1,2-dimethoxyethane, 85 deg C, 10 min

2: 1.) BuLi / 1.) hexane, THF, 20 deg C, 2.) hexane, THF, 50 deg C, 15 min

3: 98 percent / pyridinium p-toluenesulfonate / ethanol / 12 h / 20 °C

4: 97 percent / tert-butylhydroperoxide, L-(+)-diethyl tartrate, Ti(Oi-Pr)4, 4A molecular sieves / CH₂Cl₂ / 1.5 h / -40 °C

5: 99 percent / EtN(i-Pr)2 / 0.08 h / 0 °C

6: (Ph₃P)3RhCl / toluene / 16 h / 20 °C

7: pyridinium p-toluenesulfonate / ethanol / 0.08 h

8: 30 percent / BF₃*OEt₂ / CH₂Cl₂ / 0 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; Wilkinson's catalyst; n-butyllithium; diethyl (2R,3R)-tartrate; 4 A molecular sieve; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; sodium hydride; N-ethyl-N,N-diisopropylamine; In ethanol; dichloromethane; toluene;

DOI:10.1039/c39930001823

Reference yield:

(1R,3S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-formyl-3-hydroxy-2,2-dimethyl-6-methylene-cyclohexanecarboxylic acid ethyl ester (136611-34-2) + [(E)-7-(2-Ethoxy-ethoxy)-6-methyl-2-oxo-hept-5-enyl]-phosphonic acid diethyl ester → (1R,3R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-[(1E,6E)-8-(2-ethoxy-ethoxy)-7-methyl-3-oxo-octa-1,6-dienyl]-3-hydroxy-2,2-dimethyl-6-methylene-cyclohexanecarboxylic acid ethyl ester

Guidance literature:

With sodium hydride; Yield given. Multistep reaction; 1.) 1,2-dimethoxyethane, 0 deg C, 20 min, 2.) 1,2-dimethoxyethane, 85 deg C, 10 min;

DOI:10.1039/c39930001823

upstream raw materials:

(1R,3S,5S)-ethyl 5-<(tert-butyldimethylsilyl)oxy>-3-hydroxy-3-hydroxymethyl-2,2-dimethyl-6-methylenecyclohexanecarboxylate