95863-87-9

Upstream product

• 128388-09-0 (5R,4S,2S)-4-acetoxy-5-hydroxymethyl-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(2-(trimethylsilyl)ethyl) diester 
• 132592-40-6 (2S,4S,5R)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-(2-trimethylsilanyl-ethyl) ester 
• 191800-45-0 (2S,4S,5R)-N-benzyloxycarbonyl-5-hydroxymethyl-4-hydroxy-2-methoxycarbonylpyrrolidine 
• 95863-88-0 (2S,4S,5R)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 
• 148429-58-7 (5S,7aS)-1,6-dioxo-3,3-bis(trifluoromethyl)-tetrahydro-pyrrolo<1,2-c>oxazole-5-carboxylic acid ethyl ester 
• 146499-36-7 (2R,3S,5S)-2-Benzoyloxymethyl-3-benzyloxy-5-vinyl-pyrrolidine-1-carboxylic acid benzyl ester 
• 146499-23-2 (2R,3S,5S)-2-Benzoyloxymethyl-3-benzyloxy-5-formyl-pyrrolidine-1-carboxylic acid benzyl ester 
• 146499-24-3 (2S,4S,5R)-5-Benzoyloxymethyl-4-benzyloxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 
• 43139-78-2 5-(N-benzyloxycarbonyl)amino-5-deoxy-1,2-O-isopropylidene-β-L-iduronolactone 
• 40773-64-6 methyl 4,6-O-benzylidene-3-deoxy-ribo-hexopyranoside 
• 24905-47-3 methyl 2-azido-4,6-O-benzylidene-2,3-dideoxy-α-D-arabino-hexopyranoside 
• 14929-15-8 Toluene-4-sulfonic acid (4aR,6S,7R,8aS)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester 
• 51-35-4 4R-4-hydroxyproline 
• 145473-26-3 methyl N-(carbobenzyloxy)-4-hydroxy-5-(1',2',3',4'-tetrahydroxybutyl)prolinate 

Downstream Products

• 95863-90-4 (1S,4S,6R)-6-Hydroxymethyl-3-oxo-2-oxa-5-aza-bicyclo[2.2.1]heptane-5-carboxylic acid benzyl ester 
• 95863-95-9 (2S,4S,5R)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-(3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl) ester 
• 95863-93-7 (2S,4S,5R)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester; compound with dicyclohexyl-amine 
• 95863-94-8 (2S,4S,5R)-4-Acetoxy-5-acetoxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester; compound with dicyclohexyl-amine 
• 95863-89-1 (2S,4S,5R)-4-Acetoxy-5-acetoxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 
• 95863-88-0 (2S,4S,5R)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 

Relevant academic research and scientific papers

Polyhydroxylated pyrrolidine and 2-oxapyrrolizidine as glycosidase inhibitors

Using D-serine as a chiral precursor, a polyhydroxylated pyrrolidine (1), its derivatives bearing carboxylate, phosphate and phosphonate groups (2-4) and an oxapyrrolizidine (5) were synthesized. The pyrrolidine ring was formed by intramolecular amino-mercuration. The bicyclic scaffold of oxapyrrolizidine was further constructed by an intramolecular attack of the carbamate group on the iodomethyl group. Compounds 1 and 5 were found to inhibit β-glucosidase and α-galactosidase, respectively, in a competitive manner, whereas compounds 2, 3 and 4 did not produce significant inhibition against glycosidases. The Royal Society of Chemistry 2013.

An asymmetric dihydroxylation route to (-)-bulgecinine

The stereoselective synthesis of (-)-bulgecinine is reported from L-aspartic acid using Sharpless asymmetric dihydroxylation and intramolecular cyclization via nucleophilic displacement of a-tosylate as key steps.

Palladium-catalyzed DYKAT of butadiene monoepoxide: Enantioselective total synthesis of (+)-DMDP, (-)-bulgecinine, and (+)-broussonetine G

Palladium catalyzed asymmetric allylic alkylation reaction of an amine with two equivalents of butadiene monoxide allows for the expedient synthesis of trans- and cis-2,5-dihydropyrroles. The versatility of these chiral synthons towards the synthesis of a wide variety of iminosugar natural products was demonstrated with the short and high yielding asymmetric syntheses of (+)-DMDP, and (-)-bulgecinine. In addition, the first total synthesis of (+)-broussonetine G, a potent glycosidase inhibitor, is described along with the assignment of its relative and absolute stereochemical configuration.

An efficient stereoselective synthesis of (2S,4S,5R)-(-)- and (2R,4R,5S)-(+)-bulgecinine

A short synthetic route to (-)-and (+)-bulgecinine, the amino acid moiety of the bulgecins was achieved from the readily available nonchiral pool starting material cis-2-butene-1,4-diol employing a Claisen orthoester rearrangement and Sharpless asymmetric

An efficient stereoselective synthesis of (2S,4S,5R)-(-)-bulgecinine

N-Benzyl-N-carbobenzyloxy-O-tert-butyldimethylsilyl-d-serinal (6) was reacted under Barbier conditions with allyl bromide affording diastereoselectively (82:18) the anti-adduct 5, which was subsequently transformed into (2S,4S,5R)-(-)-bulgecinine (1).

Total synthesis of (-)-bulgecinine

A short synthetic route to (-)-bulgecinine (1), the amino acid moiety of bulgecins, was established by using 1,3-dipolar cycloaddition of N-benzyl- α-methoxycarbonylmethanimine N-oxide (6) to a chiral allylic alcohol (5) with moderate threo selectivity as the key reaction.

An efficient, stereoselective synthesis of (-)-bulgecinine from (S)-aspartic acid

A stereoselective synthesis of (2S,4S,5R)-4-hydroxy-5-hydroxymethylproline 1 starting from (S)-aspartic acid 2 is described. The key step of the synthesis is the [Rh(OAc)2]2 catalyzed stereospecific transformation (de >98%) of the hexafluoroacetone protected diazoketone 5 into the 4-oxoproline derivative 7. The keto function of 7 was reduced with high diastereoselectivity (de >88%) to give the 4-cis-hydroxyproline derivative 8. After deprotection (-)-bulgecinine 1 was obtained from 9 on reduction of the ester moiety with LiBHEt3.

An improved procedure for the enantioselective synthesis of (+)- and (-)-cis-4-hydroxyprolines and bulgecinines

An efficient enantioselective synthesis of both the enantiomers of cis-4-hydroxy-proline and bulgecinine was accomplished starting from synthons 1 or 1'. The improved synthetic route to the aforesaid enantiomerically pure proline derivatives was established via a stereocontrolled double iodocyclization of 3(a,b) or 3'(a,b).

Asymmetric alkylations of a sultam-derived glycine equivalent: Practical preparation of enantiomerically pure α-amino acids

Alkylation of the chiral glycine derivative 2 with 'activated' organohalides under ultrasound-assisted phase-transfer catalysis or with activated and nonactivatcd organohalides in anhydrous medium provides (mostly crystalline) alkylation products 3. Acidic hydrolysis of the pure products 3 gives (aminoacyl)sultams 4 which by mild saponification furnish pure α-amino acids 5 in good overall yields from 2, along with recovered auxiliary 1 (Scheme 1). Pure ω-protected α,ω-diamino acids and α-amino-ω-(hydroxyamino)acids 12-16 are readily accessible from (ω-haloacyl)sultams 3 via reaction with N-nucleophiles followed by acidic and basic hydrolyses (Scheme 2). A reliable determination of the enantiomeric purity of α-amino acids using HPLC analysis of their N-(3,5-dinitrobenzoyl)prolyl derivatives 17 is presented.