884848-74-2

Basic information

• Product Name: (2R)-2-methoxymethoxyhexadecanal
• CAS NO: 884848-74-2
• Molecular Weight: 300.482
• Mol File: 884848-74-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (2R)-2-methoxymethoxyhexadecanal(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-2-methoxymethoxyhexadecanal(884848-74-2)
• EPA Substance Registry System: (2R)-2-methoxymethoxyhexadecanal(884848-74-2)

Safety Data

• Hazardous Substances Data: 884848-74-2(Hazardous Substances Data)

Upstream product

• 61490-71-9 (2R)-(+)-1,2-hexadecanediol 
• 629-73-2 1-Hexadecene 
• 309946-60-9 (2R)-(-)-2-O-(methoxymethyl)hexadecane-1,2-diol 

Relevant articles and documents

A short enantioselective synthesis of guggultetrol, a naturally occurring lipid

An enantioselective synthesis of the naturally occurring lipid, guggultetrol, is described with an overall yield of 24% starting from commercially available l-pentadecanol in ten linear steps. The key chiral-inducing steps include a Sharpless asymmetric epoxidation of allylic alcohol and a dihydroxylation of an α,β-unsaturated ester.

A Stereocontrolled, Efficient Synthetic Route to Bioactive Sphingolipids: Synthesis of Phytosphingosine and Phytoceramides from Unsaturated Ester Precursors via Cyclic Sulfate Intermediates

An efficient and highly enantioselective method for the preparation of D-ribo- and L-lyxo-phytosphingosines (1a,b, respectively) and phytoceramides (2a,b) has been developed. The key steps in the syntheses are as follows: (i) osmium-catalyzed asymmetric dihydroxylation of 4-O-protected (E)-α,β-unsaturated ester 5 (generated by dihydroxylation of 1-hexadecene, followed by oxidation to the aldehyde and Horner-Wadsworth-Emmons olefination), (ii) conversion to cyclic sulfate intermediate 7, and (iii) regioselective α-azidation of 7. Reduction of 4-O-protected 2-azido ester 8 via α-azidolactone 9 afforded phytosphingosine 1a. Staudinger reduction of the azido group of 8, followed by in situ N-acylation in aqueous media and reduction of the ester functionality with NaBH4/LiBr, provided phytoceramide 2a. By using a similar approach, phytosphingosine 1b was synthesized. D-erythro-4,5-Dihydrosphingosine 1c and D-erythro-4,5-dihydroceramide 2c were synthesized in high yield from 1-hexadecanol via cyclic sulfate intermediate 15. The desired configurations at C-2, C-3, and C-4 of the sphingoid chain can be accessed readily by the route described here.