69097-51-4

Basic information

• Product Name: (R)-(+)-1,2-EPOXYHEXADECANE
• Synonyms: (R)-(+)-1,2-EPOXYHEXADECANE;(R)-1,2-EPOXYHEXADECANE
• CAS NO: 69097-51-4
• Molecular Formula: C16H32O
• Molecular Weight: 240.42
• Mol File: 69097-51-4.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-(+)-1,2-EPOXYHEXADECANE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-1,2-EPOXYHEXADECANE(69097-51-4)
• EPA Substance Registry System: (R)-(+)-1,2-EPOXYHEXADECANE(69097-51-4)

Safety Data

• Hazardous Substances Data: 69097-51-4(Hazardous Substances Data)

Usage

General Description

(R)-(+)-1,2-EPOXYHEXADECANE is a chemical compound with the molecular formula C16H32O that consists of a six-membered ring containing one oxygen atom and two adjacent carbon atoms. It is a chiral epoxide, meaning it has two different enantiomers. The compound is used in various industrial applications, including as a reactant in the production of synthetic materials, such as polymers and resins. It is also used as a precursor in the synthesis of other organic compounds. Additionally, (R)-(+)-1,2-EPOXYHEXADECANE may have potential uses in the pharmaceutical industry, as it is being studied for its potential as a chiral building block in the creation of new drugs and pharmaceuticals.

Upstream product

• 7320-37-8 1,2-epoxyhexadecane 
• 629-73-2 1-Hexadecene 
• 180797-61-9 (2S)-2-iodo-n-hexadecanal 
• 180797-59-5 (2S)-1,1-dimethoxy-2-iodo-n-hexadecane 
• 180797-63-1 (2S)-2-iodo-n-hexadecan-1-ol 

Downstream Products

• 61490-71-9 (2R)-(+)-1,2-hexadecanediol 
• 1366405-32-4 C₂₂H₄₄O₄ 
• 1366405-34-6 C₃₈H₇₆O₅ 
• 402923-15-3 (2S)-2-hexadecanoylaminohexadecyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside 
• 402923-13-1 (2S)-2-azidohexadecyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside 

Relevant articles and documents

Synthesis of (2 S,3 R,5 R)-2-Azido-3,5-dihydroxynonadecane Sphingolipid Analogue

A concise and highly efficient synthesis of an enigmol analogue has been achieved. The synthetic strategy features Jacobsen's hydrolytic kinetic resolution (HKR) and epoxide opening by alkynyl boranes as the key steps.

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.

Asymmetric synthesis of (2R)- and (2S)-2-iodohexadecanal, natural inhibitors of the thyroid gland metabolism

(2R)-(+)- and (2S)-(-)-2-iodohexadecanal 1 with ee's≤89% were synthesized in five steps and 62% overall yield from chiral enol ethers Z- and/or E-7, via the iodocyclization with ICl and chromatographic separation of the resulting diastereomeric 1'-iododioxanes 8. The ee's of (2S)- and (2R)-1 have been determined after their transformation to the (R)-O-methylmandelate esters 11 and 12 or to the epoxides (2R)- and (2S)-13, respectively. Their absolute configuration has been assigned through chemical correlation with 13 and by application of Mosher's method to the esters 15 and 16 obtained by methanolysis of (2R)- and (2S)-13, respectively, followed by derivatization. Moreover, the biosynthesis and the inhibitory activity of 1 have been shown to be unstereoselective.