(3S,5S)-3,5-Bis(tert-butyldimethylsilyloxy)-2-methylene-cyclohexanone

Base Information

Chemical Name:(3S,5S)-3,5-Bis(tert-butyldimethylsilyloxy)-2-methylene-cyclohexanone
CAS No.:190062-19-2
Molecular Formula:C19H38O3Si2
Molecular Weight:371
Hs Code.:
DSSTox Substance ID:DTXSID60445559
Wikidata:Q82264016
Mol file:190062-19-2.mol

Synonyms:190062-19-2;(3S,5S)-3,5-Bis(tert-butyldimethylsilyloxy)-2-methylene-cyclohexanone;(3S,5S)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylidenecyclohexan-1-one;FT-0663224;DTXSID60445559;HMIPXZOWGMCFDW-WBVHZDCISA-N;(3S-trans)-3,5-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methylene-cyclohexanone;J-012272

Suppliers and Price of (3S,5S)-3,5-Bis(tert-butyldimethylsilyloxy)-2-methylene-cyclohexanone

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

TRC
(3S,5S)-3,5-Bis(tert-butyldimethylsilyloxy)-2-methylene-cyclohexanone
2.5mg
$ 120.00

Total 2 raw suppliers

Chemical Property of (3S,5S)-3,5-Bis(tert-butyldimethylsilyloxy)-2-methylene-cyclohexanone

Chemical Property:

PSA：35.53000
LogP:5.68630
Storage Temp.:Amber Vial, -20°C Freezer, Under inert atmosphere
Solubility.:Chloroform (Slightly), Methanol (Slightly)
Hydrogen Bond Donor Count:0
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:6
Exact Mass:370.23594814
Heavy Atom Count:24
Complexity:496

Purity/Quality:

97% ^*data from raw suppliers

(3S,5S)-3,5-Bis(tert-butyldimethylsilyloxy)-2-methylene-cyclohexanone ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CC(C)(C)[Si](C)(C)OC1CC(C(=C)C(=O)C1)O[Si](C)(C)C(C)(C)C
Isomeric SMILES:CC(C)(C)[Si](C)(C)O[C@H]1C[C@@H](C(=C)C(=O)C1)O[Si](C)(C)C(C)(C)C

Technology Process of (3S,5S)-3,5-Bis(tert-butyldimethylsilyloxy)-2-methylene-cyclohexanone

There total 5 articles about (3S,5S)-3,5-Bis(tert-butyldimethylsilyloxy)-2-methylene-cyclohexanone 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%

: 195607-88-6
(1S,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohexanol

: 190062-19-2
(3S,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohexanone

Guidance literature:: With Dess-Martin periodane; In dichloromethane;
DOI:10.1021/jo970957t

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 190062-19-2
(3S,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohexanone

Guidance literature:: Multi-step reaction with 3 steps

1: 91 percent / DIPEA, DMAP / CH₂Cl₂ / 0.67 h / -78 °C

2: 95 percent / K₂CO₃ / methanol / 2 h

3: 90 percent / Dess-Martin reagent / CH₂Cl₂

With dmap; potassium carbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane;
DOI:10.1021/jo970957t

Reference yield:

: 195607-85-3
Acetic acid (1S,5S)-5-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohexyl ester

: 190062-19-2
(3S,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohexanone

Guidance literature:: Multi-step reaction with 4 steps

1: 57 percent / SeO₂, pyridine N-oxide / dioxane / 2 h / Heating

2: 91 percent / DIPEA, DMAP / CH₂Cl₂ / 0.67 h / -78 °C

3: 95 percent / K₂CO₃ / methanol / 2 h

4: 90 percent / Dess-Martin reagent / CH₂Cl₂

With pyridine N-oxide; dmap; selenium(IV) oxide; potassium carbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; methanol; dichloromethane;
DOI:10.1021/jo970957t