78138-99-5

Upstream product

• 132487-16-2 methyl 3,5-di-O-benzyl-2-deoxy-D-ribofuranoside 
• 158976-92-2 1,3-dibenzyloxy-2-propyl-diazoacetate 
• 533-67-5 2-Deoxy-D-ribose 
• 16838-89-4 2,3,5-tri-O-benzyl-D-ribofuranose 
• 6160-50-5 3,5-di-O-benzyl-2-deoxy-D-ribofuranose 
• 51255-17-5 1-O-methyl-2-deoxy-D-ribofuranoside 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 
• 34371-14-7 2-deoxy-D-ribonolactone 

Downstream Products

• 139870-42-1 (3S,4R)-3,5-bis(benzyloxy)pentane-1,4-diol 
• 834895-36-2 (4S,5R)-4-benzyloxy-5-benzyloxymethylpyrrolidin-2-one 
• 1053652-61-1 2-((2S,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-ethanol 
• 213255-15-3 (4aR,5R,6S,8S,8aS)-8-Benzyloxy-8a-benzyloxymethyl-6-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2,5-trimethyl-hexahydro-benzo[1,3]dioxine 
• 213255-10-8 2-[2-benzyloxy-1-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-butyl]-3-methyl-but-3-enoic acid ethyl ester 
• 213255-23-3 [(S)-3-Benzyloxy-3-((4S,5R)-4-benzyloxymethyl-5-isopropenyl-2,2-dimethyl-[1,3]dioxan-4-yl)-propoxy]-tert-butyl-dimethyl-silane 
• 213255-21-1 (2R,3S,4S)-4-Benzyloxy-3-benzyloxymethyl-6-(tert-butyl-dimethyl-silanyloxy)-2-isopropenyl-hexane-1,3-diol 
• 213255-06-2 (5S,5aS,9aR,9bS)-5-Benzyloxy-5a-benzyloxymethyl-7,7,9b-trimethyl-1,5,5a,9,9a,9b-hexahydro-4H-2,6,8-trioxa-3-aza-cyclopenta[a]naphthalene 
• 213255-11-9 (S)-3-Benzyloxy-3-((4S,5R)-4-benzyloxymethyl-5-isopropenyl-2,2-dimethyl-[1,3]dioxan-4-yl)-propan-1-ol 
• 213255-14-2 (S)-3-Benzyloxy-3-((4S,5R)-4-benzyloxymethyl-5-isopropenyl-2,2-dimethyl-[1,3]dioxan-4-yl)-propionaldehyde oxime 

Relevant academic research and scientific papers

Synthesis of polyhydroxylated quinolizidine and indolizidine scaffolds from sugar-derived lactams via a one-pot reduction/Mannich/Michael sequence

A direct approach to the synthesis of indolizidine and quinolizidine scaffolds of iminosugars is described. The presented strategy is based on a one-pot sugar lactam reduction with Schwartz's reagent followed by a diastereoselective Mannich/Michael tandem reaction of the resulting sugar imine with Danishefsky's diene. The stereochemical course of the investigated reaction has been explained in detail. The obtained bicyclic products are attractive building blocks for the synthesis of various naturally occurring polyhydroxylated alkaloids and their derivatives.

Organocatalytic conversion of ribose and other protected carbohydrate derivatives into 2-deoxy-lactones

We report the simultaneous reduction of the 2-position and oxidation of the anomeric position in several protected furanosyl and pyranosyl sugar derivatives, mediated through NHC catalysis. This reaction allows the one-step access to highly valuable 2-deoxy-sugars from abundant 2-oxygenated sugar derivatives. Georg Thieme Verlag Stuttgart · New York.

A new DNA building block, 4′-selenothymidine: Synthesis and modification to 4′-seleno-AZT as a potential anti-HIV agent

The first synthesis of 4′-selenothymidine (1), a novel DNA building block, and 4′-seleno-AZT (2) was accomplished from 2-deoxy-d-ribose via stereoselective formation of 2-deoxy-4-seleno-d-furanose 17 and a Pummerer-type base condensation as key steps. 4′-

Enantioselective Syntheses of 2-Deoxyxylono-1,4-lactone and 2-Deoxyribono-1,4-lactone from 1,3-Dioxan-5-yl Diazoacetates

1,3-Dioxan-5-yl diazoacetates are valuable substrates for highly diastereoselective and enantio-selective carbon-hydrogen insertion reactions. trans-2-(tert-Butyl)-1,3-dioxan-5-yl diazoacetate is a direct precursor to 2-deoxyribono-1,4-lactone in up to 81% ee, whereas cis-2-(tert-butyl)-1,3-dioxan-5-yl diazoacetate yields only the protected 2-deoxyxylono-1,4-lactone in up to 96% ee. However, trans-2-aryl-1,3-dioxan-5-yl diazoacetate (aryl = phenyl or 2-naphthyl) forms the precursor to 2-deoxyxylono-1,4-lactone in up to 95% ee but with the mirror image configuration of that produced from the trans-2-(tert-butyl) analogue. The catalysts that are most suitable for these carbon-hydrogen insertion reactions are chiral dirhodium(II) carboxamidates. 1,3-Dialkoxy-2-propyl diazoacetates give mainly 2-deoxyxylono-1,4-lactone derivatives (>90:10) with generally high enantiocontrol, but replacement of hydrogen at the 2-position of these 2-propyl diazoacetates led to a mixture of products.

Benzylation of aldonolactones with benzyl trichloroacetimidate

A number of aldono-1,4-lactones have been converted to their perbenzylated derivatives by treatment with benzyl trichloroacetimidate. 2,3,6-Trideoxy-D-erythro-hexono-1,4-lactone could be benzylated in dichloromethane, but lactones containing two or more h