95341-64-3

Upstream product

• 17645-37-3 (2RS)-hydroxymethyl-1-tosylpyrrolidine-(3SR,4RS)-diol 
• 17645-37-3 (2RS)-hydroxymethyl-1-tosylpyrrolidine-(3SR,4RS)-diol 
• 117781-10-9 (2S,3R,4S)-N-tert-butyloxycarbonyl-3,4-dihydroxy-3,4-O-isopropylidene-proline 
• 6322-07-2 D-gulono-1,4-lactone 
• 67642-42-6 2,3,5,6-di-O-isopropylidene-D-gulono-1,4-lactone 
• 138228-39-4 (3S,4S)-3,4-dibenzoyloxy-2-cyanopyrrolidine 
• 147-85-3 L-proline 
• 4298-08-2 trans-3-hydroxy-L-proline 
• 1393792-72-7 tert-butyl (4R,5S,E)-4,5-dihydroxy-4,5-O-isopropylidene-6-(tert-butyldimethylsilyloxy)hex-2-enoate 
• 117781-13-2 (3aR,4S,6aS)-tert-butyl 4-formyl-2,2-dimethyldihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylate 
• 117859-45-7 methanesulfonic acid (S)-((4R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-((4S,5S)-5-methanesulfonyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl ester 
• 117858-83-0 N-benzyl-1,4-dideoxy-2,3:5,6-di-O-isopropylidene-1,4-imino-D-allitol 
• 117956-54-4 (3aR,4R,6aS)-tert-butyl 4-((S)-1,2-dihydroxyethyl)-2,2-dimethyldihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylate 
• 117859-47-9 N-benzyl-1,4-dideoxy-5,6-O-isopropylidene-1,4-imino-D-allitol 

Downstream Products

• 138228-51-0 (2S,3S,4S)-1-benzyloxycarbonyl-3,4-dihydroxy-2-methoxycarbonylpyrrolidine 
• 138228-52-1 (2R,3S,4S)-1-benzyloxycarbonyl-3,4-dihydroxy-2-methoxycarbonylpyrrolidine 

Relevant academic research and scientific papers

Discovery of New Fe(II)/α-Ketoglutarate-Dependent Dioxygenases for Oxidation of l-Proline

Genome mining for novel Fe(II)/α-ketoglutarate-dependent dioxygenases (αKGDs) to expand the enzymatic repertoire in the oxidation of l-proline is reported. Through clustering of proteins, we predicted regio- and stereoselectivity in the hydroxylation reaction and validated this hypothesis experimentally. Two novel byproducts in the reactions with enzymes from Bacillus cereus and Streptomyces sp. were isolated, and the structures were determined to be a 3,4-epoxide and a 3,4-diol, respectively. The mechanism for the formation of the epoxide was investigated by performing an 18O-labeling experiment. We propose that the mechanism proceeds via initial cis-3-hydroxylation followed by ring closure. A biocatalytic step was run on subgram quantities of starting material without any significant optimization of the conditions. However, the substrate concentration was 40-fold higher than the usual reported titers for recombinant P450-mediated hydroxylations, showing the synthetic potential of αKGDs on a preparative scale.

Studies on the selectivity of proline hydroxylases reveal new substrates including bicycles

Studies on the substrate selectivity of recombinant ferrous-iron- and 2-oxoglutarate-dependent proline hydroxylases (PHs) reveal that they can catalyse the production of dihydroxylated 5-, 6-, and 7-membered ring products, and can accept bicyclic substrates. Ring-substituted substrate analogues (such hydroxylated and fluorinated prolines) are accepted in some cases. The results highlight the considerable, as yet largely untapped, potential for amino acid hydroxylases and other 2OG oxygenases in biocatalysis.

Diversity oriented concise asymmetric synthesis of azasugars: A facile access to l-2,3-trans-3,4-cis-dihydroxyproline and (3S,5S)-3,4,5-trihydroxypiperidine

Diversity oriented concise asymmetric syntheses of l-2,3-trans-3,4-cis-dihydroxyproline and (3S,5S)-3,4,5-trihydroxypiperidine have been developed from (R)-glycidol. The key step of the synthesis is Sharpless asymmetric dihydroxylation on enantiomerically pure TBDMS protected allylic alcohol 14 which generates the triol intermediate 15 in excellent de. The (2R,3R,4S)-2,3-dihydroxypentanoate derivative 15 was subsequently converted to natural pyrrolidine azasugar 1 and non-natural piperidine azasugar 4 under cascade reaction conditions in good yields.

Stereospecific cyclization strategies for α,ε-dihydroxy-β-amino esters: Asymmetric syntheses of imino and amino sugars

A range of biologically significant imino and amino sugars [1,4-dideoxy-1,4-imino-D-allitol, 3,6-dideoxy-3,6-imino-L-allonic acid, (3 R,4 S)-3,4-dihydroxy-L-proline, 1,5-anhydro-4-deoxy-4-amino-D-glucitol, and 1,5-anhydro-4-deoxy-4-amino-L-iditol] has bee

Synthesis of dihydroxylated prolines and iminocyclitols from five-membered endocyclic enecarbamates. Total synthesis of the potent glycosidase inhibitor (2R,3R,4R,5R)-2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine (DMDP)

cis- and trans-3,4-Dihydroxylated prolines and the iminocyclitol 1,4-dideoxy-1,4-imino ribitol were synthesized employing a strategy involving the Heck arylation of five-membered endocyclic enecarbamates with aryldiazonium salts followed by oxidative cleavage of the electron-rich aromatic ring. The total synthesis of the potent α- and β-glucosidase inhibitor (2R,3R,4R,5R)-2,5-hydroxymethyl-3,4-dihydroxypyrrolidine (DMDP) was also achieved by the same strategy in ten steps from a chiral five-membered enecarbamate in 12% overall yield.

Toward a general strategy for the synthesis of 3,4-dihydroxyprolines from pentose sugars

A general strategy is proposed, wherein a pentose sugar γ-lactone can be converted, via a series of nine reactions, to a 3,4-dihydroxyproline, suitably protected for use in peptide synthesis. Thus, D-ribonolactone (6) has been converted to N-fluorenylmethoxycarbonyl-3,4-di-O-tert-butyldimethylsilyloxy-D-2,3-cis-3, 4-cis-proline (7) in 18.9% overall yield. Likewise, L-arabinonolactone (11) has been converted to N-fluorenylmethoxycarbonyl-3,4-di-O-tert-butyldimethylsilyloxy-L-2,3-cis-3, 4-trans-proline (36) in 13.7% overall yield and L-lyxonolactone (12) to N-fluorenylmethoxycarbonyl- 3,4-di-O-tert-butyldimethylsilyloxy-L-2,3-trans-3,4-cis-proline (37) in 11.2% overall yield. These building blocks have also been fully deprotected to give the free amino acids. We believe that this series of reactions ought to be applicable to the synthesis of any of the eight stereoisomers of 3,4-dihydroxyproline, by judicious selection of the pentose starting material.

Synthesis of l-2,3-trans-3,4-cis-dihydroxyproline building blocks for peptide synthesis

L-2,3-trans-3,4-cis-N-Fluorenylmethoxycarbonyl-3,4-dihydroxy-3,4-O- isopropylidineproline (9) has been prepared from D-gulonolactone in nine steps and an overall yield of 22%. Compound 9 has been converted to its allyl ester 13. Compounds 9 and 13 were investigated as building blocks for the incorporation of dihydroxyproline into peptides, with compound 9 serving as a carboxyl component and compound 13 as a precursor to an amino component for peptide coupling reactions. Their utility was demonstrated by the synthesis of dipeptides 11 and 15.

Efficient synthesis of a new aminoazasugar and dihydroxyprolines from an endocyclic enecarbamate

A novel procedure for the synthesis of trans-2,3-(2-aminomethyl)-cis-3,4-dihydroxypyrrolidine (a new aminoazasugar) and cis-2,3- and trans-2,3-cis-3,4-dihydroxyprolines is presented. Starting from the known endocyclic enecarbamate 1-carbobenzyloxy-2-pyrro

Total synthesis of both enantiomers of trans-2,3-cis-3,4-dihydroxyproline

Both enantiomers of trans-2,3-cis-3,4-dihydroxyproline, 4 and 5, have been stereoselectively synthesized from 2,3-O-isopropylidene-D-glyceraldehyde 1, by taking advantage of a divergent and parallel synthetic strategy, utilizing N-(tert-butoxycarbonyl)-2-(tert-butyldimethylsiloxy)pyrrole (TBSOP) as the common four-carbon synthon.

(±)-4-amino-4,5-dideoxyribose, (±)-4-amino-4-deoxyerythrose, and (±)-dihydroxyproline derivatives from N-dienyl-γ-lactams

Hetero-Diels-Alder cycloaddition of acylnitroso dienophile 4 with the N-(butadienyl)pyrrolidinone derivatives 2a,b led with complete regioselectivity to the oxazine adducts 5a,b. Sequential osmylation, protection of the ensuing glycol, and reduction of th