82722-22-3

Basic information

• Product Name: Oxirane, tetradecyl-, (2S)-
• CAS NO: 82722-22-3
• Molecular Formula: C16H32O
• Mol File: 82722-22-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Oxirane, tetradecyl-, (2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Oxirane, tetradecyl-, (2S)-(82722-22-3)
• EPA Substance Registry System: Oxirane, tetradecyl-, (2S)-(82722-22-3)

Safety Data

• Hazardous Substances Data: 82722-22-3(Hazardous Substances Data)

Upstream product

• 7320-37-8 1,2-epoxyhexadecane 
• 172477-13-3 (2S,3Z)-hexadec-3-ene-1,2-diol acetonide 
• 61490-70-8 (2S)-(-)-1,2-hexadecanediol 
• 544-63-8 n-tetradecanoic acid 
• 13266-02-9 n-tridecyltriphenylphosphonium bromide 
• 765-09-3 1-bromotridecane 
• 178150-83-9 (2S)-hexadecan-1,2-diol-1-tosylate 

Downstream Products

• 178150-84-0 (2S,2'S)-1'-O-(2'-hydroxyhexadecyl)-2,3-O-isopropylidene glycerol 

Relevant articles and documents

A convenient resolution of long-chain alkyl epoxides with Jacobsen's salen(Co)III(OAc) catalysts

Non-racemic terminal long-chain alkyl epoxides are prepared from racemic epoxides and 1 mol% (R,R)- and (S,S)-salen(Co)III catalysts following a modified procedure for kinetic resolution. The ee's for all epoxides (C-10, C-12, C-14, C-16, C-18, C-20) exceed 95% and the chemical yields range from 85% to 95%.

Syntheses and interfacial behaviour of neoglycolipid analogues of glycosyl ceramides

Four glycosyl ceramides analogues having D-galactose or 2-acetamido-2-deoxy-D-glucose moieties linked to enantiomeric lipids have been synthesised to study their interfacial behaviour at the air | water interface. The lipid chains were prepared in two steps by opening 1,2-epoxyhexadecane using Jacobsen kinetic hydrolytic resolution (KHR) followed by an azidosilylation reaction of the diol so obtained. Glycosylation reactions were realised either with 2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl trichloroacetimidate or 1,3,4,6-tetra-O-acetyl-2-allyloxycarbonylamino-2-deoxy-β-D-glucopyranose as donors and (2R)- or (2S)-2-azidohexadecanol derivatives as acceptors. Transformation of the azido glycosides into N-acylated products was done by a modified Staudinger reaction in the presence of fatty acyl chlorides. The four neoglycolipids are able to form a condensed monolayer at the air | water interface; their π-A isotherm diagrams are similar to that described for the natural glycosyl ceramides. The detailed analysis of the isotherms, taking into account the chirality of the lipid chains, allowed to determine the contribution of the different parts of the molecule under the monolayer packing.