121742-14-1

Basic information

• Product Name: (3S,4R)-6-[(benzyloxycarbonyl)amino]-5,6-dideoxyhex-2-ulose
• Synonyms: (3S,4R)-6-[(benzyloxycarbonyl)amino]-5,6-dideoxyhex-2-ulose
• CAS NO: 121742-14-1
• Molecular Weight: 297.308
• Mol File: 121742-14-1.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (3S,4R)-6-[(benzyloxycarbonyl)amino]-5,6-dideoxyhex-2-ulose(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4R)-6-[(benzyloxycarbonyl)amino]-5,6-dideoxyhex-2-ulose(121742-14-1)
• EPA Substance Registry System: (3S,4R)-6-[(benzyloxycarbonyl)amino]-5,6-dideoxyhex-2-ulose(121742-14-1)

Safety Data

• Hazardous Substances Data: 121742-14-1(Hazardous Substances Data)

Upstream product

• 96-26-4 dihydroxyacetone 
• 65564-05-8 3-[(benzyloxycarbonyl)amino]propanal 
• 34637-22-4 3-[(N-benzyloxycarbonyl)amino]propanol 
• 56-81-5 glycerol 
• 501-53-1 benzyl chloroformate 
• 57-04-5 dihydroxyacetone phosphate 

Downstream Products

• 53185-12-9 D-fagomine 
• 475630-67-2 (2S,3R,4S)-2-(hydroxymethyl)piperidine-3,4-diol 

Relevant articles and documents

Synthesis of non-natural carbohydrates from glycerol and aldehydes in a one-pot four-enzyme cascade reaction

A simple procedure has been developed for the synthesis of enantio- and diastereomerically pure carbohydrate analogues from glycerol and a variety of aldehydes in one pot using a four-enzyme cascade reaction. As a proof of concept of the usefulness of this enzymatic catalytic cascade the naturally occurring azasugar d-fagomine was synthesized. This work highlights the potential value of using enzymes in cascade reactions to selectively form complex products that by previous traditional organic chemistry could only be obtained via repeated isolation and purification of intermediates.

Structure-guided redesign of d-fructose-6-phosphate aldolase from E. coli: Remarkable activity and selectivity towards acceptor substrates by two-point mutation

Structure-guided re-design of the acceptor binding site of d-fructose-6-phosphate aldolase from E. coli leads to the construction of FSA A129S/A165G double mutant with an activity between 5- to >900-fold higher than that of wild-type towards N-Cbz-aminoal

Fructose-6-phosphate aldolase in organic synthesis: Preparation of D-fagomine, N-alkylated derivatives, and preliminary biological assays

(Chemical Equation Presented) D-Fructose-6-phosphate aldolase (FSA) mediates a novel straightforward two-step chemo-enzymatic synthesis of D-fagomine and some of its N-alkylated derivatives in 51% isolated yield and 99% de. The key step is the FSA-catalyzed aldol addition of simple dihydroxyacetone (DHA) to N-Cbz-3-aminopropanal. The use of FSA greatly simplifies the enzymatic procedures that used dihydroxyacetonephosphate or DHA/esters. Some N-alkyl derivatives synthesized elicited antifungal and antibacterial activity as well as enhanced inhibitory activity, and selectivity against β-galactosidase and α-glucosidase.