115509-95-0

Upstream product

• 129247-81-0 2,3:5,6-di-O-isopropylidene-4-O-methanesulfonyl-D-mannononitrile 
• 35023-80-4 2,3:5,6-di-O-isopropylidene-D-mannose oxime 
• 117770-02-2 (3aS,4S,6aR)-5-benzyl-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyrrole 
• 7115-24-4 (R)-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]((4R,5R)-2,2-dimethyl-5-{[(methylsulfonyl)oxy]methyl}-1,3-dioxolan-4-yl)methyl methanesulfonate 
• 3969-61-7 2,3,5,6-di-isopropyIidene-1,4-dihydroxy-D-mannitol 
• 7757-38-2 2,3,5,6-di-O-isopropylidene-D-mannofuranose 
• 98362-00-6 Methanesulfonic acid (R)-[(4R,5R)-5-(benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl ester 
• 864163-31-5 (3S,4S,5R)-1-Benzyl-5-((S)-1,2-bis-benzyloxy-ethyl)-3,4-dihydroxy-pyrrolidin-2-one 
• 1053259-78-1 (2R,3S,4R)-2-((S)-1,2-Bis-benzyloxy-ethyl)-3,4-dihydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 864163-32-6 (2R,3S,4R)-1-Benzyl-2-((S)-1,2-bis-benzyloxy-ethyl)-pyrrolidine-3,4-diol 
• 864163-29-1 N-benzyl-N-[1-(1,2-bis-benzyloxy-ethyl)-allyl]-acrylamide 
• 864163-30-4 (R)-1-Benzyl-5-((S)-1,2-bis-benzyloxy-ethyl)-1,5-dihydro-pyrrol-2-one 
• 950747-93-0 (1R,5S)-N-(tert-butoxycarbonyl)-5,6-O-isopropylidene-5,6-dihydroxy-2-pyrroline 
• 950747-91-8 (3R,4S)-N-(tert-butoxycarbonyl)-N-(prop-1-enyl)-4,5-O-isopropylidene-4,5-dihydroxypent-1-en-3-amide 

Downstream Products

• 105888-78-6 (3aS,4R,6aR)-4-Formyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

Epimerization of C5 of an: N -hydroxypyrrolidine in the synthesis of swainsonine related iminosugars

Epimerization of C5 of an N-hydroxypyrrolidine ring by regioselective oxidation to a nitrone followed by diastereoselective reduction provides a new approach to the synthesis of swainsonine and related compounds. The only protection in the synthesis of the potent mannosidase inhibitor DIM (1,4-dideoxy-1,4-imino-d-mannitol) was the acetonation of d-mannose.

Asymmetric synthesis of d -proline, d -pipecolic acid, (2 R,3 S,4 R)-3,4-dihydroxyproline, and 1,4-Dideoxy-1,4-imino- d -talitol from a Common Precursor

Methodology involving stereoselective aza-Michael addition and ring-closing metathesis as key steps has been developed for the preparation of (2R)-pipecolic acid, (2R)-proline, (2R,3S,4R)-3,4-dihydroxyproline, and the known glycosidase inhibiting azasugar 1,4-dideoxy-1,4-imino-d-talitol from a common starting material namely (R)-cyclohexylideneglyceraldehyde in good overall yields. Georg Thieme Verlag Stuttgart New York.

Synthesis of 1,4-dideoxy-1,4-imino-derivatives of d-allitol, l-allitol and d-talitol: a stereo selective approach for azasugars

A stereo selective approach for the azasugars 1,4-dideoxy-1,4-imino-d-allitol, l-allitol, and 1,4-dideoxy-1,4-imino-d-talitol is described for different olefin compounds I derived from (R)-2,3-O-isopropylidine glyceraldehyde, l-ascorbic acid, and d-isoascorbic acid by using vinyl Grignard addition, allylation, RCM, and dihydroxylation as the key steps.

The first asymmetric synthesis of 1,4-dideoxy-1,4-imino-D-talitol

The first stereoselective synthesis of 1,4-dideoxy-1,4-imino-D-Talitol has been achieved in 24% overall yield from conveniently protected (S)-glyceraldimine (1), which is easily prepared from inexpensive D-mannitol. The synthesis is based on the addition

Potential Glycosidase Inhibitors: Synthesis of 1,4-Dideoxy-1,4-imino Derivatives of D-Glucitol, D- and L-Xylitol, D- and L-Allitol, D- and L-Talitol, and D-Gulitol

Conversion of 2,3,5,6-tetra-O-benzyl-D-galactofuranose (19) into its oxime and subsequent treatment with methanesulphonyl chloride gave 2,3,5,6-tetra-O-benzyl-4-O-methylsulphonyl-D-galactonitrile (21).Reductive cyclization by sodium borohydride/cobalt(II)

SYNTHESIS FROM D-MANNOSE OF 1,4-DIDEOXY-1,4-IMINO-L-RIBITOL AND OF THE α-MANNOSIDASE INHIBITOR 1,4-DIDEOXY-1,4-IMINO-D-TALITOL

The syntheses of 1,4-dideoxy-1,4-imino-L-ribitol and of 1,4-dideoxy-1,4-imino-D-talitol from D-mannose are described. 1,4-Dideoxy-1,4-imino-D-talitol is a specific and competitive inhibitor of human liver α-mannosidase in vitro and also blocks the lysosomal catabolism of asparigine-linked glycans of glycoproteins in vivo.