332366-75-3

Upstream product

• 20590-54-9 1,2-O-isopropylidene-5-O-(triphenylmethyl)-α-D-erythro-pentofuranos-3-ulose 
• 124-63-0 methanesulfonyl chloride 
• 302582-03-2 3-amino-3-C-cyano-3-deoxy-5-O-trityl-1,2-O-isopropylidene-α-D-xylofuranose 

Downstream Products

• 332366-87-7 1,2-O-isopropylidene-5-O-trityl-α-D-erythro-pentofuranose-3-spiro-3'-(4'-amino-5'H-2',3'-dihydroisothiazole-1',1'-dioxide) 
• 721924-32-9 3-N-allyl-3-amino-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-N-methanesulfonyl-5-O-trityl-α-D-ribofuranose 
• 721924-31-8 3-amino-3-N-benzyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-N-methanesulfonyl-5-O-trityl-α-D-ribofuranose 
• 721924-42-1 1,2-O-isopropylidene-5-O-trityl-α-D-erythro-pentofuranose-3-spiro-3'-(4'-amino-2'-N-benzyl-5'H-2',3'-dihydroisothiazole-1',1'-dioxide) 
• 332366-83-3 1,2-O-isopropylidene-5-O-trityl-α-D-erythro-pentofuranose-3-spiro-3'-(4'-amino-2'-N-methyl-5'H-2',3'-dihydroisothiazole-1',1'-dioxide) 
• 332366-79-7 3-amino-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-N-methanesulfonyl-3-N-methyl-5-O-trityl-α-D-ribofuranose 

Relevant academic research and scientific papers

New 4-amino-5-H-2,3-dihydroisothiazole-1,1-dioxides from sugar α-aminonitriles using the CSIC reaction

4-Amino-5H-2,3-dihydroisothiazole-1,1-dioxide ring was attached to a monosaccharide ring system by carbanion-mediated sulfonate intramolecular cyclisation (CSIC) of either secondary or tertiary aminoitrilesulfonamide carbohydrate derivatives using NaH, Cs

Synthesis and transformations of [1,2-O-isopropylidene-α-D-erythro (and α-D-ribo)furanose]-3-spiro-3′-(4′-amino-5′H- 2′,3′-dihydroisothiazole-1′,1′-dioxide) derivatives

The carbanion-mediated sulfonamide cyclisations (CSIC protocols) of glyco-α-sulfonamidonitriles derived from readily available uloses 1A and 1B have been investigated using different bases (potassium carbonate, cesium carbonate, LDA and n-BuLi). As a result, a series of enantiomerically pure [1,2-O-isopropylidene-α-D-erythro (and α-D-ribo)furanose]-3-spiro- 3′-(4′-amino-5′H-2′,3′-dihydroisothiazole- 1′,1′-dioxide) derivatives have been prepared and isolated in good yields.