(2S)-3-{[tert-Butyl(dimethyl)silyl]oxy}-2-methylpropan-1-yl Tosylate

Base Information

• Chemical Name: (2S)-3-{[tert-Butyl(dimethyl)silyl]oxy}-2-methylpropan-1-yl Tosylate
• CAS No.: 222539-29-9
• Molecular Formula: C17H30O4SSi
• Molecular Weight: 358.574
• DSSTox Substance ID: DTXSID70463921
• Wikidata: Q82289021
• Mol file: 222539-29-9.mol

Synonyms:222539-29-9;(2S)-3-{[tert-Butyl(dimethyl)silyl]oxy}-2-methylpropan-1-yl Tosylate;[(2S)-3-[tert-butyl(dimethyl)silyl]oxy-2-methylpropyl] 4-methylbenzenesulfonate;(2S)-3-([Tert-butyl(dimethyl)silyl]oxy)-2-methylpropan-1-yl tosylate;DTXSID70463921;AKOS025294935;J-014610;(2S)-3-{[tert-Butyl(dimethyl)silyl]oxy}-2-methylpropan-1-ylTosylate

Chemical Property of (2S)-3-{[tert-Butyl(dimethyl)silyl]oxy}-2-methylpropan-1-yl Tosylate

Chemical Property:

• Vapor Pressure: 7.07E-07mmHg at 25°C
• Boiling Point: 420.1oC at 760 mmHg
• Flash Point: 207.8oC
• PSA: 60.98000
• LogP: 5.43900
• Storage Temp.: Refrigerator
• Solubility.: Dichloromethane, Ether, Ethyl Acetate, Methanol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 358.16340714
• Heavy Atom Count: 23
• Complexity: 454

Purity/Quality:

98%Min ^*data from raw suppliers

(2S)-3-{[tert-Butyl(dimethyl)silyl]oxy}-2-methylpropan-1-ylTosylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OCC(C)CO[Si](C)(C)C(C)(C)C
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)OC[C@@H](C)CO[Si](C)(C)C(C)(C)C

Technology Process of (2S)-3-{[tert-Butyl(dimethyl)silyl]oxy}-2-methylpropan-1-yl Tosylate

There total 4 articles about (2S)-3-{[tert-Butyl(dimethyl)silyl]oxy}-2-methylpropan-1-yl Tosylate 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%

(R)-3-(tert-butyldimethylsilyloxy)-2-methylpropan-1-ol (112057-64-4) + p-toluenesulfonyl chloride (98-59-9) → (2S)-toluene-4-sulfonic acid 3-(tert-butyldimethylsilanyloxy)-2-methylpropyl ester (222539-29-9,885266-52-4)

Guidance literature:

In pyridine; at 0 ℃; for 12h;

DOI:10.1002/1099-0690(200008)2000:15<2745::AID-EJOC2745>3.0.CO;2-I

Reference yield:

(S)-3-(tert-butyldimethylsilyloxy)-2-methylpropionic acid methyl ester (93454-85-4) → (2S)-toluene-4-sulfonic acid 3-(tert-butyldimethylsilanyloxy)-2-methylpropyl ester (222539-29-9,885266-52-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / CH₂Cl₂; hexane / -40 - 20 °C

2: 92 percent / DMAP / CH₂Cl₂ / 16 h / 20 °C

With dmap; In hexane; dichloromethane;

DOI:10.1021/jo051526a

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (2S)-toluene-4-sulfonic acid 3-(tert-butyldimethylsilanyloxy)-2-methylpropyl ester (222539-29-9,885266-52-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / imidazole / dimethylformamide / 5 h / 20 °C

2: DIBAL-H / tetrahydrofuran; toluene / 3 h / -50 °C

3: pyridine / 5 h / 0 °C

With pyridine; 1H-imidazole; diisobutylaluminium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo034371k

upstream raw materials:

(R)-3-(tert-butyldimethylsilyloxy)-2-methylpropan-1-ol

p-toluenesulfonyl chloride

(S)-3-(tert-butyldimethylsilyloxy)-2-methylpropionic acid methyl ester

tert-butyldimethylsilyl chloride

Downstream raw materials:

(R)-1-(tert-butyldimethylsilyloxy)-4-(tert-butyldiphenylsilyloxy)-2-methylbutane

(2R,4RS,6R)-1-tert-butyldimethylsilyloxy-2,6-dimethyl-4-phenylsulfonyl-7-tetrahydropyranyloxyheptane

tert-Butyl-{(4E,8E)-(2R,6R,10R,11R)-11-[4-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-undecyloxy)-benzyloxy]-2,6,10-trimethyl-dodeca-4,8-dienyloxy}-dimethyl-silane

tert-Butyl-{(4E,8E)-(2R,6S,10R,11R)-11-[4-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-undecyloxy)-benzyloxy]-2,6,10-trimethyl-dodeca-4,8-dienyloxy}-dimethyl-silane