69097-51-4

Usage

Uses

Used in Synthetic Material Production:
(R)-(+)-1,2-EPOXYHEXADECANE is used as a reactant for the production of synthetic materials, such as polymers and resins. Its unique structure contributes to the development of these materials, enhancing their properties and performance.
Used in Pharmaceutical Industry:
(R)-(+)-1,2-EPOXYHEXADECANE is used as a precursor in the synthesis of other organic compounds. It holds potential in the pharmaceutical industry, as it is being investigated for its use as a chiral building block in the creation of new drugs and pharmaceuticals, which could lead to advancements in medical treatments.
Used in Chemical Synthesis:
In the chemical industry, (R)-(+)-1,2-EPOXYHEXADECANE is used as a versatile building block for the synthesis of various organic compounds. Its unique structure allows for the development of new molecules with specific properties, contributing to the expansion of the chemical library and the discovery of novel applications.

Upstream product

• 180797-63-1 (2S)-2-iodo-n-hexadecan-1-ol 
• 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 

Downstream Products

• 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 
• 61490-71-9 (2R)-(+)-1,2-hexadecanediol 

Relevant academic research and scientific papers

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.

Asymmetric synthesis of (+)-passifloricin A and its 6-epimer

Stereoselective total syntheses of the antiprotozoal natural product (+)-passifloricin A and its C-6 epimer have been achieved in ～5% overall yield. The strategy is based on Jacobsen epoxidation, Grubbs' metathesis and an Evans' intramolecular oxa-Michael reaction.

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.

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%.

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.