(3S)-4-{[Tert-butyl(dimethyl)silyl]oxy}-3-methylbutyl phenyl sulfone

Base Information

• Chemical Name: (3S)-4-{[Tert-butyl(dimethyl)silyl]oxy}-3-methylbutyl phenyl sulfone
• CAS No.: 218613-98-0
• Molecular Formula: C17H30O3SSi
• Molecular Weight: 342.575
• DSSTox Substance ID: DTXSID00472541
• Nikkaji Number: J1.005.239D
• Wikidata: Q82301516
• Mol file: 218613-98-0.mol

Synonyms:218613-98-0;(3S)-4-{[TERT-BUTYL(DIMETHYL)SILYL]OXY}-3-METHYLBUTYL PHENYL SULFONE;[(2S)-4-(benzenesulfonyl)-2-methylbutoxy]-tert-butyl-dimethylsilane;(3S)-4-([TERT-BUTYL(DIMETHYL)SILYL]OXY)-3-METHYLBUTYL PHENYL SULFONE;SCHEMBL6996198;DTXSID00472541;AKOS025294920;J-014322

Chemical Property of (3S)-4-{[Tert-butyl(dimethyl)silyl]oxy}-3-methylbutyl phenyl sulfone

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 423.111°C at 760 mmHg
• Flash Point: 209.69°C
• PSA: 51.75000
• Density: 1.011g/cm³
• LogP: 5.58910
• Solubility.: Dichloromethane, Ether, Ethyl Acetate
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 342.16849252
• Heavy Atom Count: 22
• Complexity: 426

Purity/Quality:

98%Min ^*data from raw suppliers

(3S)-4-{[tert-Butyl(dimethyl)silyl]oxy}-3-methylbutylPhenylSulfone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(CCS(=O)(=O)C1=CC=CC=C1)CO[Si](C)(C)C(C)(C)C
• Isomeric SMILES: C[C@@H](CCS(=O)(=O)C1=CC=CC=C1)CO[Si](C)(C)C(C)(C)C

Technology Process of (3S)-4-{[Tert-butyl(dimethyl)silyl]oxy}-3-methylbutyl phenyl sulfone

There total 7 articles about (3S)-4-{[Tert-butyl(dimethyl)silyl]oxy}-3-methylbutyl phenyl sulfone 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%

(3S)-3-methyl-1-phenylsulfonylbutan-4-ol (121587-29-9) + tert-butyldimethylsilyl chloride (18162-48-6) → (-)-(3S)-4-{[tert-butyl(dimethyl)silyl]oxy}-3-methylbutyl phenyl sulfone (218613-98-0)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 3h;

DOI:10.1021/jo0007480

Reference yield: 96.0%

(benzenesulfonyl)methyllithium (116511-95-6) + (2R)-toluene-4-sulfonic acid 3-(tert-butyldimethylsilanyloxy)-2-methylpropyl ester (299430-30-1,885266-52-4) → (-)-(3S)-4-{[tert-butyl(dimethyl)silyl]oxy}-3-methylbutyl phenyl sulfone (218613-98-0)

Guidance literature:

In tetrahydrofuran; at -20 - 20 ℃; for 12h;

DOI:10.1016/S0040-4039(98)02026-7

Reference yield:

(-)-(3S)-4-{[tert-butyl(diphenyl)silyl]oxy}-3-methylbutyl phenyl sulfone (263900-30-7) → (-)-(3S)-4-{[tert-butyl(dimethyl)silyl]oxy}-3-methylbutyl phenyl sulfone (218613-98-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / TBAF / tetrahydrofuran / 10 h / 20 °C

2: 99 percent / imidazole / dimethylformamide / 3 h / 0 - 20 °C

With 1H-imidazole; tetrabutyl ammonium fluoride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jo0007480

upstream raw materials:

(benzenesulfonyl)methyllithium

(2R)-toluene-4-sulfonic acid 3-(tert-butyldimethylsilanyloxy)-2-methylpropyl ester

(3S)-3-methyl-1-phenylsulfonylbutan-4-ol

tert-butyldimethylsilyl chloride

Downstream raw materials:

epothilone B

(4S,7R,8S,9S,13Z,16S,1'E)-4,8-di-tert-butyldimethylsilyloxy-5,5,7,9,13-pentamethyl-16-[1-methyl-2-(2-methyl-1,3-thiazol-4-yl)-1-ethenyl]-1-oxa-13-cyclohexadecene-2,6-dione

epothilone D

(5S,8R,9S,10S,17S,Z)-9-(tert-butyldimethylsilyloxy)-5-(2-hydroxyethyl)-2,2,3,3,6,6,8,10,14,19,19,20,20-tridecamethyl-17-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)-4,18-dioxa-3,19-disilahenicos-14-en-7-one