34311-63-2

Upstream product

• 23202-83-7 5-benzyl-1,2-O-isopropylidene-α-D-xylofuranose 
• 100-39-0 benzyl bromide 
• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 100-52-7 benzaldehyde 
• 1333-82-0 chromium(VI) oxide 
• 6893-65-8 1,2-di-O-isopropylidene-5-O-tosyl-D-xylofuranose 
• 1125-88-8 benzaldehyde dimethyl acetal 

Downstream Products

• 26293-59-4 3-deoxy-3-methylene-1,2-O-(1-methyethylidene)-5-O-(phenylmethyl)-α-D-xylofuranose 
• 2592-42-9 5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose 
• 785805-82-5 5-O-benzyl-1,2-O-isopropylidene-3-C-trichloromethyl-α-D-ribose 
• 785805-83-6 (3S)-3-azido-5-O-benzyl-3-deoxy-1,2-O-isopropylidene-3-C-methoxycarbonyl-α-D-erythro-pentose 
• 1012796-05-2 5-O-benzyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-{[(methoxycarbonyl)methyl]amino}-α-D-ribofuranose 
• 1012796-06-3 5-O-benzyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-{[(S)-1-(methoxycarbonyl)-3-methylbutyl]amino}-α-D-ribofuranose 
• 1310019-04-5 1,2-O-isopropylidene-5-O-benzyl-3-deoxy-3-dibenzylamino-α-D-ribofuranose 
• 1310019-00-1 (2S,3R,4S,5S)-2-allyl-4-benzylamino-5-(benzyloxymethyl)tetrahydrofuran-3-ol 
• 1310019-01-2 (2S,3R,4S,5S)-2-allyl-5-(benzyloxymethyl)-4-(dibenzylamino)-tetrahydrofuran-3-ol 
• 1310018-99-5 1,2-O-isopropylidene-5-O-benzyl-3-deoxy-3-benzylamino-α-D-ribofuranose 
• 1339886-12-2 5-O-benzyl-3-deoxy-3-C-(2-fluoroethylidene)-1,2-O-isopropylidene-α-D-erythropentofuranose 
• 1339886-14-4 5-O-benzyl-3-deoxy-3-fluoro-1,2-O-isopropylidene-3-C-(phenylethynyl)-α-D-xylofuranose 
• 1339886-16-6 5-O-benzyl-3-deoxy-3-fluoro-1,2-O-isopropylidene-3-C-(E)-styryl-α-D-glucofuranose 
• 1339886-08-6 5-O-benzyl-1,2-O-isopropylidene-3-C-(E)-styryl-α-D-ribofuranose 

Relevant academic research and scientific papers

Dimerization of aldosuloses and aldonolactones into branched higher carbon sugars

Homo-dimerizations of a variety of aldosulose and aldonolactone derivatives via aldol and Claisen reactions have been achieved, leading to novel branched higher carbon sugars in a highly stereoselective manner.

High 1,3-trans stereoselectivity in nucleophilic substitution at the anomeric position and β-fragmentation of the primary alkoxyl radical in 3-amino-3-deoxy-ribofuranose derivatives: Application to the synthesis of 2- epi -(-)-jaspine B

The high inverse stereoselectivity in the nucleophilic substitution at the anomeric position of 3-amino-3-deoxy-ribofuranose derivatives is reported. This unprecedented stereoselectivity is explained in terms of preferential nucleophilic attack on the "inside face" of the respective five-membered ring oxocarbenium ion that orients pseudoequatorially to the benzylamine group placed at the C-3 position. In addition, an unusual β-fragmentation of a primary alkoxyl radical generated from its corresponding N-phthalimide derivative was achieved, and thus taking advantages of both reactions, the total synthesis of 2-epi-(-)-jaspine B was completed.

O-acetyl-ADP-ribose non-hydrolyzable analogs

Compounds, compositions and methods for modulating cell death in target cells, particularly cancer cells are provided. The compounds are analogs of O-acetyl-ADP-ribose (OAADPr).

Synthesis and biochemical evaluation of O-acetyl-ADP-ribose and N-acetyl analogs

Synthetic routes for the preparation of O-acetyl-ADP-ribose and two novel non-hydrolyzable analogs containing an N-acetyl are described and shown to interact with the macro domain of histone protein H2A1.1. The Royal Society of Chemistry.

The synthesis of carbohydrate α-amino acids utilizing the Corey-Link reaction

Various carbohydrate ketones (uloses) have been treated with chloroform under strongly basic conditions to yield trichloromethyl tertiary alcohols. These alcohols, when subjected to the conditions of the modified Corey-Link reaction (sodium azide and 1,8-

(3R,4S)-3,4,5-Trihydroxy-4-methylpentylphosphonic acid, an isosteric phosphonate analogue of 2-C-methyl-D-erythritol 4-phosphate, a key intermediate in the new pathway for isoprenoid biosynthesis

2-C-Methyl-D-erythritol 4-phosphate (MEP) is the first intermediate in the mevalonate-independent pathway for isoprenoid biosynthesis presenting the branched C5 isoprene skeleton. Enantiopure (3R,4S)-3,4,5-trihydroxy- 4-methylpentylphosphonic a

Synthesis of enantiomerically pure alkylated D-erythritols and D-threitols from D-xylose-structural influences on their mesophasic behavior

1-O-Alkyl and 2-O-alkyl-D-threitol enantiomers were derived from 5-O-alkyl and 5-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranoses. The analogous erythritol derivatives were also obtained from the same precursors via analogous D-ribose monoacetals. Mesophas

Synthesis of anomerically pure vinyl sulfone-modified pent-2-enofuranosides and hex-2-enopyranosides: A group of highly reactive Michael acceptors for accessing carbohydrate based synthons

Syntheses of the benzyl or the trityl protected α- and β-anomers of vinyl sulfone-modified pent-2-enofuranosides have been initiated by the ring opening of the suitably masked methyl α-lyxofuranosyl-epoxide or methyl β-ribofuranosyl-epoxide or by the nucleophilic displacement of the leaving groups in benzyl protected 3-O-tosyl xylofuranoside and 3-O-mesyl ribofuranoside by p-thiocresol. In case of the latter set of starting materials, α- and β-methyl glycosides formed in almost equal ratio only from the derivatives of D-xylose. For the synthesis of α- and β-anomers of vinyl sulfone-modified hex-2-enopyranosides, a D-glucose derivative was selected over a D-allose derivative as the starting material because the former almost exclusively produced the required methyl pyranosides whereas the latter produced a mixture. All sulfides were converted to vinyl sulfone-modified carbohydrates by the sequential application of oxidation, mesylation and base induced elimination reactions.

Contribution of the adenine base to the activity of adenophostin A investigated using a base replacement strategy

Syntheses of 3'-O-α-D-glucopyranosyl-1-β-D-ribofuranosidoimidazole 2',3',4'-trisphosphate (7) and 3'-O-α-D-glucopyranosyl-9-β-D-ribofuranosidopurine 2',3',4'-trisphosphate (8), two analogues of the superpotent 1D-myo-inositol 1,4,5-trisphosphate receptor agonist adenophostin A (2), are described. 5-O-Benzyl-1,2-O-isopropylidene-α-D-ribofuranose was prepared by an improved route from 1,2-O-isopropylidene-α-D-xylofuranose and was coupled with 3,4-di-O-acetyl-2,6-di-O-benzyl-D-glucopyranosyl dimethyl phosphite to give 3',4'-di-O-acetyl-2',5,6'-tri-O-benzyl-3-O-α-D-glucopyranosyl-1,2-O-isopropy lidene-α-D-ribofuranose. Removal of the isopropylidene acetal and subsequent acetylation gave the central disaccharide 1,2,3',4'-tetra-O-acetyl-2',5,6'-tri-O-benzyl-3-O-α-D-glucopyranosyl-D-ribof uranose. Vorbruggen condensation with activated imidazole or purine gave the required β-substituted derivatives which were further elaborated to 7 and 8, respectively. Radioligand binding assays to hepatic InsP3 receptors and functional assays of Ca2+ release from permeabilized hepatocytes gave a rank order of potency of the ligands 2 ? 8 > 7 ? Ins(1,4,5)P3 indicating that the N6-amino group of 2 is of little importance for activity and that a minimum of a two-fused-ring nucleobase is required for activity to exceed that of Ins(1,4,5)P3. The role of the adenine base in the activity of the adenophostins is discussed. This general method should facilitate ready access to nucleobase-modified adenophostin analogues for SAR studies.

Convergent synthesis of adenophostin A analogues via a base replacement strategy

The first totally synthetic base-modified analogues of the natural product and potent D-myo-inositol 1,4,5-trisphosphate receptor agonist adenophostin A were efficiently synthesised from D-xylose and D-glucose using methodology employing base and surrogate base addition to a common disaccharide intermediate.