302582-03-2

Basic information

• Product Name: 3-amino-3-C-cyano-3-deoxy-5-O-trityl-1,2-O-isopropylidene-α-D-xylofuranose
• Synonyms: 3-amino-3-C-cyano-3-deoxy-5-O-trityl-1,2-O-isopropylidene-α-D-xylofuranose
• CAS NO: 302582-03-2
• Molecular Weight: 456.541
• Mol File: 302582-03-2.mol

Chemical Properties

• CAS DataBase Reference: 3-amino-3-C-cyano-3-deoxy-5-O-trityl-1,2-O-isopropylidene-α-D-xylofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 3-amino-3-C-cyano-3-deoxy-5-O-trityl-1,2-O-isopropylidene-α-D-xylofuranose(302582-03-2)
• EPA Substance Registry System: 3-amino-3-C-cyano-3-deoxy-5-O-trityl-1,2-O-isopropylidene-α-D-xylofuranose(302582-03-2)

Safety Data

• Hazardous Substances Data: 302582-03-2(Hazardous Substances Data)

Upstream product

• 20590-54-9 1,2-O-isopropylidene-5-O-(triphenylmethyl)-α-D-erythro-pentofuranos-3-ulose 
• 7677-24-9 trimethylsilyl cyanide 

Downstream Products

• 721924-30-7 3-amino-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-N-phenylmethanesulfonyl-5-O-trityl-α-D-ribofuranose 
• 1434741-49-7 3-amino-3-deoxy-1,2-O-isopropylidene-3-C-(1H-tetrazol-5-yl)-5-O-trityl-α-D-ribofuranose 
• 330196-73-1 (3R)-3,3-(1,3-diazaspiro-2,4-dioxo)-5-O-trityl-1,2-O-isopropylidene-α-D-ribofuranose 
• 721924-45-4 1,2-O-isopropylidene-5-O-trityl-α-D-erythro-pentofuranose-3-spiro-3'-(4'-amino-2'-N-benzyl-5'-phenyl-5'H-2',3'-dihydroisothiazole-1',1'-dioxide) 
• 721924-34-1 3-amino-3-N-benzyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-N-phenylmethanesulfonyl-5-O-trityl-α-D-ribofuranose 
• 721924-44-3 1,2-O-isopropylidene-5-O-trityl-α-D-erythro-pentofuranose-3-spiro-3'-(4'-amino-2'-N-methyl-5'-phenyl-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 
• 721924-51-2 1,2:5,6-di-O-isopropylidene-α-D-ribo-hexofuranose-3-spiro-3'-(4'-amino-2'-N-benzyl-5'-phenyl-5'H-2',3'-dihydroisothiazole-1',1'-dioxide) 
• 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) 
• 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) 
• 667923-88-8 1,2-O-isopropylidene-α-D-erythro-pentofuranose-3-spiro-3'-(4'-amino-5'-phenyl-5'H-2',3'-dihydroisothiazole-1',1'-dioxide) 
• 667923-76-4 (1S,3R,7R,8R,12S,14R)-12-amino-9-N-benzyl-5,5-dimethyl-10-thia-10,10-dioxide-9-aza-2,4,6,13-tetraoxatetracyclo[6.6.0.0^3,7.0^8,12]tetradecane 
• 667923-90-2 1,2-O-isopropylidene-α-D-erythro-pentofuranose-3-spiro-3'-(4'-amino-2'-N-methyl-5'-phenyl-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 articles and documents

Spirohydantoins from D-ribose as new potent enzymatic inhibitors

Anomeric spirohydantoin derivatives from monosaccharides are known for various biological properties. We describe herein the synthesis of the 3-spirohydantoin derivatives of D-allose and D-ribose. The key step is the stereoselective glyco-α-aminonitrile formation from ulose derivatives of D-glucose and D-xylose using titanium tetra-isopropoxide as a mild and efficient catalyst. Target compounds were synthesized from these intermediates. The glucidic moiety was partially or totally deprotected under acidic conditions. These new heterocyclic monosaccharidic derivatives are potent glycogen phosphorylase inhibitors.

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.

Stereoselective synthesis of α-aminonitriles at non-anomeric positions of monosaccharides

α-Aminonitriles have been stereoselectively introduced at non-anomeric positions of monosaccharides, in which the carbon C-α is one of the atoms of the sugar ring. Target compounds were prepared from various ulose derivatives and amines using titanium(IV) isopropoxide as a mild and effective Lewis acid. (C) 2000 Elsevier Science Ltd.