147923-01-1

Basic information

• Product Name: (2R,3R,4R,5S)-2-hydroxymethyl-5-methylpyrrolidine-3,4-diol
• CAS NO: 147923-01-1
• Molecular Weight: 147.174
• Mol File: 147923-01-1.mol

Chemical Properties

• CAS DataBase Reference: (2R,3R,4R,5S)-2-hydroxymethyl-5-methylpyrrolidine-3,4-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4R,5S)-2-hydroxymethyl-5-methylpyrrolidine-3,4-diol(147923-01-1)
• EPA Substance Registry System: (2R,3R,4R,5S)-2-hydroxymethyl-5-methylpyrrolidine-3,4-diol(147923-01-1)

Safety Data

• Hazardous Substances Data: 147923-01-1(Hazardous Substances Data)

Upstream product

• 147860-06-8 5-azide-5,6-dideoxy-L-xylo-hexo-2-ulose 
• 209786-19-6 Methanesulfonic acid (R)-1-{(4S,5R)-5-[(R)-1-tert-butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethyl ester 
• 251901-85-6 phosphoric acid mono-(3R,4R-dihydroxy-5S-methyl-pyrrolidin-2R-ylmethyl) ester 
• 251901-83-4 phosphoric acid mono-(5S-amino-3S,4R-dihydroxy-2-oxo-hexyl) ester 
• 133473-08-2 methyl 3,4;5,6-di-O-isopropylidene-2-amino-2-deoxy-D-mannate 
• 117462-55-2 methyl 2-azido-2-deoxy-3,4:5,6-di-O-isopropylidene-D-mannonate 
• 161867-44-3 (S)-tert-Butoxycarbonylamino-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-acetic acid methyl ester 
• 190600-70-5 1-O-acetyl-2-tert-butoxycarbonylamino-2-deoxy-3,4:5,6-di-O-isopropylidene-D-mannitol 
• 209786-18-5 {(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-[(4R,5R)-5-((R)-1-hydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-carbamic acid tert-butyl ester 
• 1037306-48-1 (2R,3R,4R,5S)-3,4-bis(benzyloxy)-2-(hydroxymethyl)-5-methylpyrrolidine 
• 190600-72-7 1-O-acetyl-2-tert-butoxycarbonylamino-2-deoxy-3,4-O-isopropylidene-6-O-methanesulfonyloxy-D-mannitol 
• 190600-74-9 1-O-(tert-butyldimethylsilyl)oxy-2-tert-butylcarbonylamino-2-deoxy-3,4-O-isopropylidene-5,6-epoxy-D-mannitol 
• 190600-71-6 1-O-acetyl-2-tert-butoxycarbonylamino-2-deoxy-3,4-O-isopropylidene-D-mannitol 
• 190600-69-2 [(R)-2-Hydroxy-1-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-ethyl]-carbamic acid tert-butyl ester 

Relevant articles and documents

Stereoselective Aldol Additions Catalyzed by Dihydroxyacetone Phosphate-Dependent Aldolases in Emulsion Systems: Preparation and Structural Characterization of Linear and Cyclic Iminopolyols from Aminoaldehydes

The potential of dihydroxyacetone phosphate (DHAP)-dependent aldolases to catalyze stereoselective aldol additions is, in many instances, limited by the solubility of the acceptor aldehyde in aqueous/co-solvent mixtures. Herein, we demonstrate the efficiency of emulsion systems as reaction media for the class I fructose-1,6-b isphosphate aldolase (RAMA) and class II recombinant rhamnulose-1-phosphate aldolase from E. coli (RhuA)catalyzed aldol addition between DHAP and N-benzyloxycarbonyl (N-Cbz) aminoaldehydes. The use of emulsions improved the RAMA-catalyzed aldol conversions by three to tenfold relative to those in conventional DMF/ water mixtures. RhuA was more reactive than RAMA towards the N-Cbz aminoaldehydes regardless of the reaction medium. With (S)- or (R)-Cbz-alaninal, RAMA exhibited preference for the R enantiomer, while RhuA had no enantiomeric discrimination. The linear N-Cbz aminopolyols thus obtained were submitted to catalytic intramolecular reductive amination to afford the corresponding iminocyclitols. This reaction was diastereoselective in all cases examined; the face selectivity was controlled by the stereochemistry of the newly formed hydroxyl group originating from the aldehyde. Characterization of the resulting iminocyclitols allowed the assessment of the diastereoselectivity of the enzymatic aldol reactions with respect to the N-protected aminoaldehyde. RAMA formed single diastereoisomers from N-Cbz-glycinal and from both enantiomers of N-Cbz-alaninal, while 14% of the epimeric product was observed from N-Cbz-3-aminopropanal. Diastereoselectivity from RhuA was lower than that observed from RAMA. Interestingly, a single diastereoisomer was formed from (S)-Cbz-alaninal, whereas only a 34% diastereomeric excess was observed from its enantiomer (i.e., (R)-Cbz-alaninal).

Polyhydroxylated pyrrolidines: Synthesis of trideoxy-2,5-iminohexitols

A series of naturally occurring pyrrolidine alkaloids and analogues, with the general structure of trideoxy-2,5-iminohexitols (imino- or azasugars), have been enantiosynthesized using triorthogonally protected pyrrolidines, previously prepared from commercial D-fructose, as homochiral starting materials. The inhibitory activity of some of the described compounds against glycosidases and glycosyltransferases makes them potential therapeutic agents. Georg Thieme Verlag Stuttgart.

Facile approach towards phosphorylated azasugars as potential glycosyl phosphate mimics

A sequence of two chemoselective reductions enables the stereoselective synthesis of phosphorylated azasugars starting from products of dihydroxyacetonephosphate-dependent aldolases.

Simple synthetic route to polyhydroxylated pyrrolidines and piperidines

A short and simple synthetic route to polyhydroxylated piperidines and pyrrolidines were described with D-glucurono-δ-lactone as chiral educt. Key reaction steps included selective cleavage of terminal isopropylidene group of compound 12 with Dowex 50W-X8 resin (H+ form), regioselective ring opening of epoxide 16 and intramolecular nucleophilic amination of compound 14 and 18.

Chemo-enzymatic synthesis of five-membered azasugars as inhibitors of fucosidase and fucosyltransferase: An issue regarding the stereochemistry discrimination at transition states

Three new 5-membered aza sugars which inhibit bovine α-fucosidase with K(i) values in the μM range have been prepared based on aldolase reactions.