99096-86-3

Upstream product

• 5349-07-5 D-O¹,O³;O⁴,O⁶-((R,S)-dibenzylidene)-galactitol 
• 28224-73-9 1,3:4,6-di-O-benzylidene-D-mannitol 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 100-52-7 benzaldehyde 
• 69-65-8 mannitol 
• 608-66-2 D-galactitol 

Downstream Products

• 17618-04-1 2,5-di-O-benzyl-D-mannitol 
• 94926-01-9 2-O-benzyl-D-glyceraldehyde dimethylacetal 
• 20196-69-4 1,2,5,6-tetra-O-benzyl-D-mannitol 
• 76227-09-3 (R)-2-benzyloxy-3-hydroxy-propionaldehyde 
• 89157-42-6 1-O-hexadecyl-2-O-benzyl-D-glyceraldehyde 
• 84415-89-4 (S)-2-benzyloxy-3-hexadecyloxy-propan-1-ol 
• 91326-84-0 1-O-hexadecyl-2-O-benzyl-sn-glycero-3-phosphocholine 
• 166102-94-9 3-O-allyl-2-O-benzyl-D-glyceraldehyde dimethylacetal 
• 166102-97-2 3-O-hexadecyl-2-O-benzyl-D-glyceraldehyde dimethylacetal 
• 99096-96-5 (3S,4R)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-pentanoic acid methyl ester 
• 99096-95-4 (3R,4R)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-pentanoic acid methyl ester 
• 99096-89-6 (2R,3R)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-hex-5-en-3-ol 
• 99112-28-4 (2R,3S,4S,5R)-2,5-Bis-benzyloxy-1,6-bis-(tert-butyl-dimethyl-silanyloxy)-hexane-3,4-diol 
• 98944-53-7 (S)-2-O-benzyl-3-O-(tert-butyldimethylsilyl)-D-glyceraldehyde 

Relevant academic research and scientific papers

New 3-O-lauroyl-2-O-benzyl-glycerol sulfonate

The hydroxy groups of D-mannitol were protected by the formation of acetals and benzylethers and then 2-O-benzyl-D-glyceraldehyde dimethylacetal was prepared after the deprotection and oxygenolysis of the protected D-mannitol. In the presence of DCC and D

Highly selective Silver(I) oxide mediated monoprotection of symmetrical diols

Treatment of symmetrical diol with Ag2O and alkyl halide gave the monoprotected derivative in good to excellent yield.

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

Chelation- and Non-Chelation-Controlled Additions to 2-O-Benzyl-3-O-(tert-butyldimethylsilyl)glyceraldehyde

2-O-Benzyl-3-O-(tert-butyldimethylsilyl)glyceraldehyde, prepared from 1,3:4,5-di-O-benzylidenemannitol, undergoes chelation- or non-chelation-controlled Grignard-type and aldol additions, depending upon the nature of the organometallic reagent used (TiCl4/Me2Zn, TiCl4/allylsilane, SnCl4/enol silane, RTi(OCHMe2)3, and BF3/allylsilane).