76227-09-3

Upstream product

• 17618-04-1 2,5-di-O-benzyl-D-mannitol 
• 4141-39-3 2-O-benzyl-D-arabinitol 
• 65877-63-6 3-O-benzyl-D-glucopyranose 
• 100-44-7 benzyl chloride 
• 100-52-7 benzaldehyde 
• 99096-86-3 1,3:4,6-di-O-benzylidene-2,5-di-O-benzyl-D-Mannitol 
• 84379-52-2 (2R,3R)-3-(benzyloxy)butane-1,2,4-triol 

Downstream Products

• 119770-85-3 (S)-5-Benzyloxy-5,6-dihydro-pyran-2-one 
• 119770-86-4 (R)-5-Benzyloxy-5,6-dihydro-pyran-2-one 
• 119770-83-1 (Z)-(S)-4-Benzyloxy-5-hydroxy-pent-2-enoic acid ethyl ester 
• 119770-82-0 (E)-(S)-4-Benzyloxy-5-hydroxy-pent-2-enoic acid ethyl ester 
• 119770-88-6 ethyl (4R)-benzyloxy-5-hydroxy-cis-2-pentenoate 
• 119770-84-2 ethyl (-)-[R-(E)]-4-O-benzyl-4,5-dihydroxy-2-pentenoate 
• 129492-41-7 (2R,3S)-2-Benzyloxy-5,5-diethoxy-4-nitro-pentane-1,3-diol 
• 153186-37-9 (5S,3E)-5-benzyloxy-6-hydroxy-hex-3-en-2-one 
• 202532-32-9 (2R,3S,4S)-2-Benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-nitro-butane-1,3-diol 
• 153186-41-5 Ethyl (2R,3R,4R,5S)-4-acetyl-3-<(1S)-1-(benzyloxy)-2-hydroxyethyl>-5-phenylpyrrolidine-2-carboxylate 
• 166102-97-2 3-O-hexadecyl-2-O-benzyl-D-glyceraldehyde dimethylacetal 
• 166102-94-9 3-O-allyl-2-O-benzyl-D-glyceraldehyde dimethylacetal 
• 91326-84-0 1-O-hexadecyl-2-O-benzyl-sn-glycero-3-phosphocholine 
• 84415-89-4 (S)-2-benzyloxy-3-hexadecyloxy-propan-1-ol 

Relevant academic research and scientific papers

New optically pure dimethylacetals of glyceraldehydes and their application for lipid and phospholipid synthesis

A convenient synthesis of new and enantiometrically pure 2-O-protected D-glyceraldehyde dimethylacetals as chiral C-3 building blocks for the synthesis of lipids and phospholipids is described.Benzyl- or allylethers are used as protecting groups in position 2 and 5 of D-mannitol.These intermediates are converted to 2-O-benzyl- or 2-O-alkyl-D-glyceraldehyde dimethylacetals by cleavage with periodic acid in methanol.The two dimethylacetals are useful for the synthesis of mixed chain phospholipids with natural configuration of ester-ester, ester-ether or ether-ether composition.Also, triglycerides with three different alkyl chains, ester of ether, can be prepared.As an example of the varsatility of the new intermediates, we describe the synthesis of 1-O-hexadecyl-2-O-acetyl-sn-glycero-3-phosphocho;ine, the so-called 'platelet activating factor' (PAF), via 1-O-hexadecyl-2-O-benzyl-sn-glycerol. Keywords: Synthetic phospholipids; PAF; Phospholipid analogues; Synthesis; Chiral pool; Glyceraldehyde; C-3 building blocks; Optical purity

Pyranoside Derivatives of 3-Deoxyald-2-ulosonic Acids

At pH 11.5 in 0.2M-sodium tetraborate solution and in the presence of Ni2+, 2-O-benzyl-D-arabinose reacts with oxaloacetic acid to give a 50-60percent yield of 5-O-benzyl-3-deoxyoct-2-ulosonic acids (mixed D-gluco- and D-manno-isomers).The methyl esters of these were separated and the α-methyl glycoside of the D-manno-isomer was prepared.The conformation of the compounds was established by n.m.r. spectroscopy at 250 MHz.It was observed that esterification of the carboxy-group greatly increases the stability of the glycosidic bond of 3-deoxy-D-manno-octulosonic acid while the benzyl substituent in position 5 exerts only a weak stabilising effect. 2-O-Benzyl-D-glyceraldehyde, when treated with oxaloacetic acid in the presence of Ni2+ at pH 7 in the absence of borate, yields 5-O-benzyl-3-deoxyhex-2-ulosonic acids, the predomonant D-erythro-isomer being isolated as its methyl ester.