156857-10-2

Upstream product

• 121209-13-0 (3R,4S,5R,6R)-N-Benzyl-3,4,5-tris(benzyloxy)-6-<(benzyloxy)methyl>piperidin-2-one; Pentabenzyl-D-nojirilactam 
• 128984-74-7 5-Amino-5-deoxy-3,6-di-O-benzyl-D-glucono-δ-lactam 
• 118464-50-9 6-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-D-mannono-δ-lactam 
• 172371-16-3 (3aS,6R,6aS)-6-[(R)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-4-one 
• 120027-71-6 Trifluoro-methanesulfonic acid (S)-2-(tert-butyl-diphenyl-silanyloxy)-1-((3aS,4S,6aS)-2,2-dimethyl-6-oxo-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-ethyl ester 
• 7306-64-1 2,3:5,6-di-O-isopropylidene-L-gulonolactone 
• 118493-82-6 6-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-L-mannono-δ-lactam 
• 23843-32-5 2,3-Isopropylidene-D-gulono-γ-lactone 
• 49561-21-9 (3aR,6S,6aR)-6-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one 
• 107537-94-0 (+)-Galactostatin 
• 294204-03-8 2,3-di-O-methoxymethyl-6-O-triphenylmethyl-D-galactono-δ-lactam 
• 56710-46-4 5,6-O-isopropylidene-D-galactonic acid γ-lactone 
• 223608-75-1 Acetic acid (2R,3S,4R,5S)-3,5-diacetoxy-2-acetoxymethyl-6-oxo-piperidin-4-yl ester 
• 294204-15-2 2,3-di-O-methoxymethyl-6-O-triphenylmethyl-D-iodono-δ-lactam 

Relevant academic research and scientific papers

An efficient synthesis of δ-glyconolactams by intramolecular Schmidt-Boyer reaction under microwave radiation

δ-Glyconolactams were first synthesized by the intramolecular Schmidt-Boyer reaction using corresponding δ-azidosugars as starting material. The reaction could be efficiently performed in good yields of 61-69% under microwave radiation in acid condition,

Structure-activity relationship of highly potent galactonoamidine inhibitors toward β-galactosidase (Aspergillus oryzae)

A small library of 22 N-substituted galactonoamidines was synthesized, and their structure-activity relationship for inhibition of the hydrolytic activity of β-galactosidase (Aspergillus oryzae) was evaluated. A fast screening assay in 96-well plate forma

Stereoselective synthesis of 1-deoxynojirimycin, D-glucono-δ-lactam and D-altrono-δ-lactam from a common chiral intermediate derived from D-mannitol

A stereoselective synthesis of 1-deoxynojirimycin, D-glucono-δ-lactam and D-altrono-δ-lactam were accomplished from a common chiral intermediate derived from D-mannitol. The key transformations in the synthesis include Miyashita C-2 selective endo-mode azide opening of epoxy alcohol and Sharpless asymmetric dihydroxylation. ARKAT-USA, Inc.

COMPOSITIONS COMPRISING NB-DNJ, NE-DNJ OR D-GLUCARO-DELTA-LACTAM AND THEIR USES FOR THE TREATMENT OF PAIN AND OTHER NEUROLOGICAL CONDITIONS

Methods and compositions for the treatment of conditions including stress-associated, chronic pain, and neurodegenerative conditions in a mammal using a composition comprising NB-DNJ or a compound structurally similar thereto.

Total synthesis of deoxymannojirimycin and D-mannolactam via carbonylation of 5-vinyloxazolidin-2-ones

The stereoselective synthesis of piperidine alkaloids deoxymannojirimycin and D-mannolactam from D-serine has been achieved. The key step involves palladium-catalysed decarboxylative carbonylation of a serine-derived 5-vinyloxazolidin-2-one to give 6-(tert-butyldimethylsilyloxymethyl)-3,6-dihydro-1H-pyridin-2-one which was subsequently converted into the title compounds.

All eight stereoisomeric D-glyconic-δ-lactams: Synthesis, conformational analysis, and evaluation as glycosidase inhibitors

An efficient and general synthetic route to all eight stereoisomeric D-glycono-δ-lactams has been developed. The strategy involves, as a key step, a stereodivergent δ-lactam formation with configurational retention or inversion at C-4 of a starting γ-lactone to lead to two epimers of δ-lactam from one parent γ-lactone. Conformations of eight glycono-δ-lactams were examined by X-ray crystallographic analysis and molecular modeling. Analyses of conformation and glycosidase-inhibition provide useful information for the design of new glycosidase inhibitors.

A general approach to the synthesis of dideoxy and trideoxyiminoalditols from β-D-glycosides

Imino sugars (also called azasugars), a class of compounds of which the 1,5-dideoxy and 1,5,6-trideoxyiminoalditols are members, are important glycosidase inhibitors with very high potential as drugs. Their potential therapeutic applications range from the treatment of diabetes to cancer and AIDS. We present here a general method for the preparation of such compounds with the D-gluco and D-galacto configurations starting from β-D-glycosides. The procedure is especially appealing because of its high stereoselectivity and straightforwardness. The key steps are the selective oxidation of the glycosides to hexulosonic acids and reduction of the oxime derivatives to lactams, which are further reduced to the target compounds. The C-6 position can be deoxygenated during the reduction if it bears an acetoxy group. Trideoxy imino sugars are then produced. Deacetylation prior to oxime reduction gives dideoxy compounds. (C) 2000 Elsevier Science Ltd.

A concise synthesis of unnatural (+)-5-epi-nojirimycin-δ-lactam via asymmetric reduction of a meso-imide

Nojirimycin-δ-lactam skeleton was synthesized by asymmetric reduction of a cyclic triacetyloxy meso imide with a chiral β-amino thiol ligand. The resulting product was converted to unnatural (+)-5-epi-nojirimycin-δ- lactam.

5-epi-Deoxyrhamnojirimycin is a potent inhibitor of an α-L- rhamnosidase: 5-epi-Deoxymannojirimycin is not a potent inhibitor of an α- D-mannosidase

Whereas deoxyrhamnojirimycin (LRJ) 1 shows no significant inhibition of naringinase (an α-L-rhamnosidase), its C-5 epimer 2 is a potent and specific inhibitor of the enzyme and demonstrates the value of unambiguous chemical synthesis of such materials in the evaluation of their biological properties. In contrast, moderately weak inhibition towards an α-D-mannosidase is shown by both deoxymannojirimycin (DMJ) 5 and its C-5 epimer 6. Mimics of L- rhamnose which are recognised by enzymes that synthesise or process L- rhamnose may inhibit either the biosynthesis of the sugar or its incorporation into mycobacterial cell walls, providing new strategies for the treatment of diseases such as tuberculosis and leprosy. Molecular modelling studies provide a rationale for the surprisingly potent activity of the C-5 epimer 2 compared with LRJ 1 and support a general hypothesis that potent piperidine glycosidase inhibitors mimic the 4H3 conformation of the relevant glycopyranosyl cation intermediate.

Construction of Hydroxylated Alkaloids (+/-)-Mannonolactam, (+/-)-Deoxymannojirimycin, and (+/-)-Prosopinine through Aza-Annulation

The aza-annulation of β-enamino carbonyl substrates with acrylate derivatives provides an efficient and convenient route for the regioselective construction of δ-lactams.This two-step ring-forming sequence involved initial generation of the benzyl enamine through either a condensation or conjugate addition reaction with BnNH2, followed by aza-annulation with acryloyl chloride or acrylic anhydride.Controlled by the rigid framework of the intermediate lactam, introduction of ring substituents was accomplished with high relative stereoselectivity.The carbonyl functionality, which was necessary to direct the regioselectivity of the aza-annulation reaction, was then transformed into a protected hydroxyl substituent through Baeyer-Villiger oxidation.The resultant δ-lactam product was used as a valuable intermediate in the synthesis of three natural products.Subsequent modification of this δ-lactam gave the naturally occurring α-mannosidase inhibitors (+/-)-mannonolactam and (+/-)-deoxymannojirimycin, while synthesis of the alkaloid (+/-)-prosopinine was accomplished through homologation of the lactam carbonyl.