69257-55-2

Upstream product

• 108-24-7 acetic anhydride 
• 5434-31-1 1,3-2,5-4,6-tri-O-methylene-D-mannitol 
• 7664-93-9 sulfuric acid 
• 64-19-7 acetic acid 

Downstream Products

• 36566-49-1 (4R,5R,6R,7R)-4,7-bis(hydroxymethyl)-1,3-dioxepane-5,6-diol 
• 71769-25-0 2,2'-O-methylene-bis-(3-O-trityl-sn-glycerol) 
• 154371-98-9 (12-{(R)-2-[(R)-1-(12-tert-Butoxycarbonylamino-dodecyloxymethyl)-2-trityloxy-ethoxymethoxy]-3-trityloxy-propoxy}-dodecyl)-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Synthesis of 1-O-alkyl-sn-glycerols and fluorescently labeled analogs from 2.5 O methylene D mannitol as precursor

A new approach employing 2.5 O methylene D mannitol as precursor for the synthesis of naturally occurring and fluorescently labeled alkyl glycerols is described. From 2.5 O methylene D mannitol, which was prepared according to the method of Ness et al. [1], 2,2-0-methylene-bis-(3-O-trityl)-sn-glycerol, the central product, was synthesized to an enantiomerically pure molecule in four steps. 1-O-hexadecyl-sn-glycerol was prepared by condensation of hexadecyl methanesulfonate with the central product and by subsequent detritylation and cleavage of the methylene bridge. From the alkyl glycerol the different lipid classes can be synthesized by well known strategies. To form fluorescently labeled analogs of alkyl glycerols the fluorescence marker 7-chloro-4-nitrobenzo-2-oxa-1,3-diazole (NBD-Cl) was linked with the ω-amino group of 1-O-(12-aminododecyl)-sn-grycerol. Therefore the central product was condensed with 12-N-t-BOC-aminododecyl methanesulfonate. The methylene bridge, the trityl groups and the BOC protection group were cleaved with boron trifluoride/methanol in one step. 1-O-(12-NBD-aminododecyl)-sn-grycerol is useful as a biochemical substrate to build up fluorescently labeled neutral lipids and phospholipids.

Method for the synthesis of pharmacologically active compounds and intermediates for such synthesis

A process for the preparation of an aryloxypropanolamine of the formula wherein Ar is a carbocyclic or heterocyclic aromatic group and R is an alkyl or substituted alkyl group having 1 to 6 carbon atoms, characterized in subjecting a compound of the formula STR1 to oxidative cleavage to a dialdehyde of the formula STR2 which is then made subject to reduction, amination, acetal hydrolysis, and, where required, removal of a nitrogen protective group, to the formation of a compound of formula I, or an acid addition salt thereof, a compound of formula II and the preparation thereof from mannitol.