108341-31-7

Upstream product

• 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 
• 98361-99-0 {(4R,5S)-5-[(R)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl}-carbamic acid benzyl ester 
• 98362-05-1 (R)-((4S,5R)-5-Aminomethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol 
• 35023-80-4 2,3:5,6-di-O-isopropylidene-D-mannose oxime 

Downstream Products

• 98362-02-8 3-{(2R,3S)-3-[(4R,5R)-5-(Benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxiranyl}-propionic acid ethyl ester 
• 98393-47-6 (E)-3-{(2R,3S)-3-[(4R,5R)-5-(Benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxiranyl}-acrylic acid ethyl ester 
• 85624-09-5 (3aR,9R,9aR,9bS)-octahydro-2,2-dimethyl-[1,3]dioxolo[4,5-a]indolizin-9-ol 
• 72741-87-8 swainsonine 
• 105878-90-8 (1R,5S,6R,1'S)-7-benzyloxycarbonyl-6-1',2'-dihydroxyethyl-3,3-dimethyl-2,4-dioxa-7-azabicyclo<3.3.0>octane 
• 105929-20-2 (1R,5S,6R)-7-benzyloxycarbonyl-3,3-dimethyl-6-hydroxymethyl-2,4-dioxa-7-azabicyclo<3.3.0>octane 
• 105888-78-6 (3aS,4S,6aR)-4-Formyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid benzyl ester 
• 100937-51-7 (2R,3S,4R)-2-(hydroxymethyl)pyrrolidine-3,4-diol 
• 95189-02-9 1,4-dideoxy-1,4-imino-D-mannitol 
• 98393-46-5 [(4R,5R)-5-((2R,3S)-3-Formyl-oxiranyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl]-carbamic acid benzyl ester 

Relevant academic research and scientific papers

Short synthesis of (+)-1-deoxynojirimycin via a diastereoselective reductive coupling of alkyne and -chiral aldehyde

A short, highly diastereoselective synthesis of (+)-1-deoxynojirimycin from readily available l-isoserine with overall yield of 32.0% in eight steps is described. The key step includes a diastereoselective syn-coupling reaction of Cbz-protected (S)-iso-serinal acetonide 6 and vinylzinc nucleophile, generated conveniently from a protected propargyl alcohol 7 by a hydrozirconation- transmetalation sequence. Significantly, not only does this simple flexible strategy provide a concise approach to (+)-1-deoxynojirimycin, but it also can readily be adopted for the synthesis of other stereoisomers of the 1-deoxynojirimycin family from l- or d-iso-serine through different coupling conditions and stereoselective -epoxidation of allylic alcohol 4 by the same procedures. Georg Thieme Verlag Stuttgart · New York.

Enantiospecific Total Synthesis of (-)-Swainsonine: New Aplications of Sodium Borohydride Reduction

A short, enantiospecific synthesis of (-)-swainsonine (1) from D-mannose has been achieved by a route involving, as a key step, a double cyclization of 4c.The synthesis takes adventage of new features of sodium borohydride for reducing conjugated esters and lactams.