181767-52-2

Basic information

• Product Name: 2-trimethylsilylethyl N-[(1S)-2-hydroxy-1-methyl-ethyl]carbamate
• Synonyms: 2-(Trimethylsilyl)ethyl [(2S)-1-hydroxypropan-2-yl]carbamate
• CAS NO: 181767-52-2
• Molecular Formula: C₉H₂₁NO₃Si
• Molecular Weight: 219.35
• Mol File: 181767-52-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 308.9°C at 760 mmHg
• Flash Point: 140.6°C
• Density: 0.983g/cm³
• Vapor Pressure: 6.02E-05mmHg at 25°C
• Refractive Index: 1.444
• CAS DataBase Reference: 2-trimethylsilylethyl N-[(1S)-2-hydroxy-1-methyl-ethyl]carbamate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-trimethylsilylethyl N-[(1S)-2-hydroxy-1-methyl-ethyl]carbamate(181767-52-2)
• EPA Substance Registry System: 2-trimethylsilylethyl N-[(1S)-2-hydroxy-1-methyl-ethyl]carbamate(181767-52-2)

Safety Data

• Hazardous Substances Data: 181767-52-2(Hazardous Substances Data)

Upstream product

• 20160-60-5 2-(trimethylsilyl)-ethoxycarbonyl chloride 
• 2916-68-9 2-(Trimethylsilyl)ethanol 
• 1384833-93-5 methyl (S)-2-[(2-trimethylsilylethoxy)carbonylamino]propanoate 
• 2749-11-3 (S)-Alaninol 
• 78269-85-9 carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester 2-(trimethylsilanyl)-ethyl ester 
• 80149-80-0 2-(Trimethylsilyl)ethyl 4-nitrophenyl carbonate 

Relevant articles and documents

1,5-Stereocontrol in tin(IV) halide mediated reactions between N- and S-substituted pent-2-enylstannanes and aldehydes or imines

Following transmetalation of (4S)-4-(dibenzylamino)pent-2-enyl(tributyl) stannane with tin(IV) bromide, reactions of the resulting allyltin tribromide with aldehydes gave (3Z)-1,5-syn-5-(dibenzylamino)hex-3-en-1-ols with excellent, ca. 98:2, stereocontrol. (4R)-5-Benzylthio-4-methylpent-2-enyl(tributyl) stannane similarly reacted with aldehydes to give (3Z)-1,5-anti-6-benzylthio-5- methylhex-3-en-1-ols with 87:13 stereocontrol. Although the analogous reaction of (4R)-4-benzylthiopent-2-enyl(tributyl)stannane with benzaldehyde proceeded with some stereoselectivity, 80-90:20-10, in favour of the (3Z)-1,5-syn- diastereoisomer, the yield was low due to a competing Lewis acid catalysed 1,4-elimination. N-Acylamino- and S-acylthio-pent-2-enylstannanes reacted with aldehydes with variable syn/anti-stereoselectivities. Tin(IV) chloride promoted reactions of the 4-(dibenzylamino)pent-2-enylstannane with 1- alkoxycarbonylimines gave (E)-alk-4-enoates with a modest preference for the 2,6-anti-products, 2,6-anti/2,6-syn=75:25.

Synthesis of a chiral receptor molecule with converging amidinium and hydroxy groups

The axially chiral amidinium ion 1 was synthesized by Suzuki cross coupling and by base induced cyclization of an amino nitrile intermediate. Receptor 1 may interact with guest molecules by three converging H-bond donors.