(2S)-2-[2-[(tert-Butyldimethylsilyl)oxy]ethyl]oxirane

Base Information

• Chemical Name: (2S)-2-[2-[(tert-Butyldimethylsilyl)oxy]ethyl]oxirane
• CAS No.: 95337-97-6
• Molecular Formula: C₁₀H₂₂O₂Si
• Molecular Weight: 202.369
• DSSTox Substance ID: DTXSID301214207
• Nikkaji Number: J2.466.972F
• Mol file: 95337-97-6.mol

Synonyms:SCHEMBL1712042;DTXSID301214207;95337-97-6;(2S)-2-[2-[(tert-Butyldimethylsilyl)oxy]ethyl]oxirane

Chemical Property of (2S)-2-[2-[(tert-Butyldimethylsilyl)oxy]ethyl]oxirane

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 202.138906475
• Heavy Atom Count: 13
• Complexity: 172

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OCCC1CO1
• Isomeric SMILES: CC(C)(C)[Si](C)(C)OCC[C@H]1CO1

Technology Process of (2S)-2-[2-[(tert-Butyldimethylsilyl)oxy]ethyl]oxirane

There total 2 articles about (2S)-2-[2-[(tert-Butyldimethylsilyl)oxy]ethyl]oxirane 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: 98.0%

(R)-2-(oxiran-2-yl)ethan-1-ol (76282-48-9) + tert-butyldimethylsilyl chloride (18162-48-6) → (R)-2-(2-(tert-butyldimethylsilyloxy)ethyl)oxirane (95337-97-6,110171-85-2,130659-83-5,95338-04-8)

Guidance literature:

With 1H-imidazole; In dichloromethane; for 4h;

DOI:10.1016/j.tetlet.2007.10.058

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) + (S)-2-(oxiran-2-yl)ethan-1-ol (19098-31-8,76282-48-9,84985-50-2,95404-59-4) → (2-((S)-oxiran-2-yl)ethoxy)(tert-butyl)dimethylsilane (95338-04-8,110171-85-2,130659-83-5,95337-97-6)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 4 ℃;

DOI:10.1016/S0040-4020(01)91498-X

Reference yield: 99.0%

(S)-N-tert-butyl-2-(methoxymethoxy)-3-(2-methylbutyl)benzamide (1361331-91-0) + (R)-2-(2-(tert-butyldimethylsilyloxy)ethyl)oxirane (95337-97-6,110171-85-2,130659-83-5,95338-04-8) → N-tert-butyl-6-[(S)-4-(tert-butyldimethylsilyloxy)-2-hydroxybutyl]-2-(methoxymethoxy)-3-((S)-2-methylbutyl)benzamide (1361331-98-7)

Guidance literature:

(S)-N-tert-butyl-2-(methoxymethoxy)-3-(2-methylbutyl)benzamide; With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In diethyl ether; at -78 - -40 ℃; for 2h; Inert atmosphere;

(R)-2-(2-(tert-butyldimethylsilyloxy)ethyl)oxirane; In diethyl ether; at -78 - -40 ℃; for 14h; Inert atmosphere;

DOI:10.1002/chem.201104042

upstream raw materials:

tert-butyldimethylsilyl chloride

(S)-2-(oxiran-2-yl)ethan-1-ol

(R)-2-(oxiran-2-yl)ethan-1-ol

Downstream raw materials:

2-(4-tert-Butyldimethylsilyloxy-2-hydroxybutyl)-2-phenylthiotetrahydro-2H-thiopyran

1-(4-methoxy)phenylamino-4-tert-butyldimethylsilyloxy-2-butanol

N-tert-butyl-2-[4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-butyl]-benzamide

N-tert-butyl-2-[4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-butyl]-6-methoxy-benzamide