131472-79-2

Upstream product

• 28143-91-1 (1S,2S)-2-amino-1-phenyl-1,3-diol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 131472-78-1 (1S,2S)-2-[N-(diphenylmethylene)amino]-3-O-(tert-butyldimethylsilyl)-1-phenylpropane-1,3-diol 
• 131472-75-8 methyl O-tert-butyldimethylsilyl-N-(diphenylmethylene)-L-serinate 
• 131472-78-1 2-(Benzhydrylidene-amino)-3-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-propan-1-ol 

Downstream Products

• 131751-46-7 (4S,5S)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-5-phenyl-oxazolidin-2-one 
• 800402-01-1 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [1-(S)-(tert-butyldimethylsilanyloxymethyl)-2-(S)-hydroxy-2-phenylethyl]amide 
• 800402-02-2 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [1-(S)-(tert-butyldimethylsilanyloxymethyl)-2-oxo-2-phenylethyl]amide 
• 218766-18-8 Toluene-4-sulfonic acid (4S,5S)-2-oxo-5-phenyl-oxazolidin-4-ylmethyl ester 
• 109760-77-2 L-threo-1-phenyl-2-decanoylamino-3-morpholino-1-propanol 
• 218766-19-9 (4S,5S)-4-Morpholin-4-ylmethyl-5-phenyl-oxazolidin-2-one 
• 193545-66-3 (1S,2S)-2-amino-3-morpholino-1-phenyl-1-propanol 
• 146985-90-2 (4S,5S)-4-hydroxymethyl-5-phenyloxazolidin-2-one 

Relevant academic research and scientific papers

PYRROLOPYRIDINE-2-CARBOXYLIC ACID AMIDE INHIBITORS OF GLYCOGEN PHOSHORYLASE

Compounds represented by Formula (I): or pharmaceutically acceptable salts thereof, are inhibitors of glycogen phosphorylase and are useful in the prophylactic or therapeutic treatment of diabetes, hyperglycemia, hypercholesterolemia, hyperinsulinemia, hyperlipidemia, hypertension, atherosclerosis or tissue ischemia e.g. myocardial ischemia, and as cardioprotectants.

Glycosyltransferase inhibitors: Synthesis of D-threo-PDMP, L-threo- PDMP, and other brain glucosylceramide synthase inhibitors from D- or L- serine

The synthesis of enantiomerically pure (1S,2S)-1-phenyl-2- decanoylamino-3-N-morpholino-1-propanol (L-threo-PDMP) (1a) from L-serine, and the enantiomer (LR,2R)-1-phenyl-2-decanoylamino-3-morpholino-1-propanol (D-threo-PDMP] (1b) from D-serine is reported. Reductive alkylation of the fully protected O'Donnell's Schiff base (3b) derived from D-serine provided the β-amino alcohol 5b in high yield and excellent selectivity, which yielded optically pure 1b in high yield after six steps. Three other D- threo-PDMP analogues with various amine groups have been synthesized using the same methodology, including the more potent pyrrolidine compound D- threo-PDPP (1e). A key feature of the synthesis is the isolation of tosylate (8b), which allows for the divergent synthesis of many analogues from a common advanced intermediate. The synthesis is amenable to large-scale production of D-threo-PDMP, L-threo-PDMP, and similar compounds.

2-amino-1-phenyl-propan-1,3-diol as chiral auxiliary. Application in the synthesis of cis 3-phthalimido-4-styryl-2-azetidinones

3,4-cis3,4-cis-1-N-(1'-phenyl-1',3'-dihydroxy-2'-propyl)-3-phthalimido-4 -styrylazetidinones were obtained in optically pure form by chiral Staudinger reaction. The cis-α/β-ratio could be influenced by the protective groups of the diol moiety. Removal of the chiral auxiliarity could be accomplished by direct oxidation, or by previous double bond formation, thus the 2-amino-1-phenyl-propan-1,3-diol can be regarded to a generally useful chiral auxiliary.

β-Amino alcohols from amino acids: Chelation control via Schiff bases

Sequential addition of iBu2AlH and RLi or RMgX to Schiff base esters derived from amino acids provides a simple route to β-amino alcohols. The reaction procedes without racemization, and with high threo selectivity. Several representative sphingosines are synthesized.