62362-63-4

Usage

Uses

A potent inhibitor of rat epididymal alpha-mannosidase and of apricot ?-glucosidase.

InChI:InChI=1/C6H13NO6/c7-2(1-8)3(9)4(10)5(11)6(12)13/h2-5,8-11H,1,7H2,(H,12,13)/t2-,3-,4+,5+/m1/s1

Upstream product

• 120027-72-7 (3aS,6R,7R,7aS)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridin-4-one 
• 118464-47-4 6-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-L-gulonolactone 
• 118464-49-6 (3S,4S,5R)-5-[(1R)-1-azido-2-tert-butyldimethylsilanyloxyethyl]-3,4-isopropylidenedioxytetrahydrofuran-2-one 
• 118464-48-5 Trifluoro-methanesulfonic acid (S)-2-(tert-butyl-dimethyl-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 
• 50-81-7 ascorbic acid 
• 1128-23-0 L-gulono-1,4-lactone 
• 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 
• 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 
• 120006-93-1 (3aS,6R,6aS)-6-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-4-one 
• 1053264-68-8 Trifluoro-methanesulfonic acid (S)-1-((3aS,4S,6aS)-2,2-dimethyl-6-oxo-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-trityloxy-ethyl ester 
• 294204-05-0 2,3-O-isopropylidene-6-O-triphenylmethyl-L-glucono-γ-lactone 
• 294204-06-1 5-azido-2,3-O-isopropylidene-6-O-triphenylmethyl-D-mannono-γ-lactone 
• 94840-08-1 2,3-O-isopropylidene-L-gulono-γ-lactone 

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,

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 Facile Transformation of Sugar Lactones to Azasugars

The synthesis of pyrano- and furano- sugar lactams from the corresponding lactones, in a five step sequence, is described.

PRACTICAL SYNTHESIS OF DEOXYMANNOJIRIMYCIN AND MANNONOLACTAM FROM L-GULONOLACTONE. SYNTHESIS OF L-DEOXYMANNOJIRIMYCIN AND L-MANNONOLACTAM FROM D-GULONOLACTONE.

An eight step synthesis of deoxymannojirimycin from L-gulonolactone in 25percent overall yield is reported; the key step is the formation of a δ-lactam by the reduction of a 5-azidolactone.The preparations of mannonolactam from L-gulonolactone and of L-deoxymannojirimycin and L-mannonolactam from D-gulonolactone are described.

SHORT SYNTHESES OF D-DEOXYMANNOJIRIMYCIN AND D-MANNOLACTAM FROM L-GULONOLACTONE AND OF L-DEOXYMANNOJIRIMYCIN AND L-MANNONOLACTAM FROM D-GULONOLACTONE

Short syntheses of D-deoxymannojirimycin and of D-mannolactam from L-gulonolactone are reported; identical sequences on D-gulonolactone lead to L-deoxymannojirimycin and L-mannolactam.

Enantiospecific Synthesis of D-Mannono-δ-lactam from Vitamin C

An eight-step synthesis of the glycosidase inhibitor D-mannono-δ-lactam from vitamin C is described.