(3S,5S)-3,5-Bis(tert-butyldimethylsilyloxy)-2-methyl-1-cyclohexen-1-ol 1-Trifluoromethanesulfonate

Base Information

• Chemical Name: (3S,5S)-3,5-Bis(tert-butyldimethylsilyloxy)-2-methyl-1-cyclohexen-1-ol 1-Trifluoromethanesulfonate
• CAS No.: 189894-13-1
• Molecular Formula: C20H39F3O5SSi2
• Molecular Weight: 504.759
• DSSTox Substance ID: DTXSID50441944
• Wikidata: Q82258960
• Mol file: 189894-13-1.mol

Synonyms:189894-13-1;[(3S,5S)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylcyclohexen-1-yl] trifluoromethanesulfonate;(3S,5S)-3,5-Bis(tert-butyldimethylsilyloxy)-2-methyl-1-cyclohexen-1-ol 1-Trifluoromethanesulfonate;FT-0663225;DTXSID50441944;YOIMFEXPXGPPAD-WBVHZDCISA-N

Chemical Property of (3S,5S)-3,5-Bis(tert-butyldimethylsilyloxy)-2-methyl-1-cyclohexen-1-ol 1-Trifluoromethanesulfonate

Chemical Property:

• PSA: 70.21000
• LogP: 7.78200
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 504.20088307
• Heavy Atom Count: 31
• Complexity: 786

Purity/Quality:

98% ^*data from raw suppliers

(3S,5S)-3,5-Bis(tert-butyldimethylsilyloxy)-2-methyl-1-cyclohexen-1-ol1-Trifluoromethanesulfonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(CC(CC1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)OS(=O)(=O)C(F)(F)F
• Isomeric SMILES: CC1=C(C[C@H](C[C@@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)OS(=O)(=O)C(F)(F)F
• Uses: Intermediate in the preparation of Dihydroxyvitamin D3 and associated metabolites.

Technology Process of (3S,5S)-3,5-Bis(tert-butyldimethylsilyloxy)-2-methyl-1-cyclohexen-1-ol 1-Trifluoromethanesulfonate

There total 6 articles about (3S,5S)-3,5-Bis(tert-butyldimethylsilyloxy)-2-methyl-1-cyclohexen-1-ol 1-Trifluoromethanesulfonate 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: 41.0%

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + (3S,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohexanone (190062-19-2) → Trifluoro-methanesulfonic acid (3S,5S)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-cyclohex-1-enyl ester (189894-13-1)

Guidance literature:

With L-Selectride; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1021/jo970957t

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → Trifluoro-methanesulfonic acid (3S,5S)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-cyclohex-1-enyl ester (189894-13-1)

Guidance literature:

Multi-step reaction with 4 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

4: 41 percent / L-Selectride / tetrahydrofuran / -78 - 20 °C

With dmap; L-Selectride; potassium carbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo970957t

Reference yield:

Acetic acid (1S,5S)-5-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohexyl ester (195607-85-3) → Trifluoro-methanesulfonic acid (3S,5S)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-cyclohex-1-enyl ester (189894-13-1)

Guidance literature:

Multi-step reaction with 5 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

5: 41 percent / L-Selectride / tetrahydrofuran / -78 - 20 °C

With pyridine N-oxide; dmap; selenium(IV) oxide; L-Selectride; potassium carbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane;

DOI:10.1021/jo970957t

upstream raw materials:

N,N-phenylbistrifluoromethane-sulfonimide

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

t-butyldimethylsiyl triflate

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

Downstream raw materials:

(3R,5S)-3,5-Bis[(tert-butyldimethylsilyl)oxy]-1-ethynyl-2-methylcyclohex-1-ene

TB

(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-1-trimethylsilanylethynyl-cyclohexene

Refernces