851915-72-5

Basic information

• Product Name: (2R,3R,4E)-1,2-anhydro-3-O-(benzyloxymethyl)octadec-4-ene-1,2,3-triol
• Synonyms: (2R,3R,4E)-1,2-anhydro-3-O-(benzyloxymethyl)octadec-4-ene-1,2,3-triol
• CAS NO: 851915-72-5
• Molecular Weight: 402.618
• Mol File: 851915-72-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,3R,4E)-1,2-anhydro-3-O-(benzyloxymethyl)octadec-4-ene-1,2,3-triol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4E)-1,2-anhydro-3-O-(benzyloxymethyl)octadec-4-ene-1,2,3-triol(851915-72-5)
• EPA Substance Registry System: (2R,3R,4E)-1,2-anhydro-3-O-(benzyloxymethyl)octadec-4-ene-1,2,3-triol(851915-72-5)

Safety Data

• Hazardous Substances Data: 851915-72-5(Hazardous Substances Data)

Upstream product

• 121998-84-3 (2R,3R,4E)-octadec-4-ene-1,2,3-triol 
• 114275-39-7 (2R,3R,4E)-1,3-benzylidene-4-octadecene-1,2,3-triol 
• 851915-70-3 (2R,3R,4E)-1-O-(p-tolylsulfonyl)octadec-4-ene-1,2,3-triol 
• 851915-71-4 (2R,3R,4E)-1,2-anhydrooctadec-4-ene-1,2,3-triol 
• 3587-60-8 Benzyloxymethyl chloride 

Downstream Products

• 851915-73-6 dibenzyl (3R,4R,5E)-(4-O-benzyloxymethyl-3,4-dihydroxynonadec-5-en-1-yl)phosphonate 
• 851915-74-7 dibenzyl (3S,4R,5E)-(3-azido-4-O-benzyloxymethyl-4-hydroxynonadec-5-en-1-yl)phosphonate 

Relevant articles and documents

Synthesis of sphingosine-1-phosphonate and homosphingosine-1-phosphonate

In the first approach to homosphingosine-1-phosphonate, D-glucofuranose was selectively deoxygenated at C-5. Bond cleavage between C-1 and C-2 afforded a 5-deoxy-D-threopentose intermediate. (E)-Selective Wittig reaction with a C 14-chain gave a C19-intermediate, which was readily transformed into homosphingosine. Formation of a cyclic urethane containing the 3-amino and the 4-hydroxy group of the C19-intermediate permitted regioselective introduction of the phosphonate group at C-1, thus affording the target molecule after deprotection. In a second and shorter route, C 18-sphingosine was converted to a cyclic urethane containing the 2-amino and the 3-hydroxy group of the C18-chain. C1-Chain extension by a hydroxymethyl group by introduction of cyanide led to the same C19 cyclic urethane as obtained in the first route. Similarly, the C18 cyclic urethane led to the other target molecule, namely sphingosine-1-phosphonate. The third and shortest route to homosphingosine-1- phosphonate could be based on regioselective 1-O-tosylation of 1,2,3-(trihydroxy)octadec-4-ene. Transformation into a 1,2-epoxide, then combination of C1-chain extension and introduction of a phosphonate group with methylphosphonate as reagent, and finally azide introduction, led after functional group liberation to the target molecule. As shown, also truncated derivatives are readily accessible by this route. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.