63846-98-0

Upstream product

• 4495-04-9 1,2-O-isopropylidene-α-D-allofuranose 
• 582-51-4 1,2-O-Isopropyliden-α-D-allofuranose 
• 14686-89-6 (1,2:5,6)-di-O-isopropylidene-D-gulose 
• 2595-05-3 Diacetone D-glucose 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 
• 26597-74-0 1,2:5,6-di-O-isopropylidene-β-L-talofuranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 582-51-4 1,2-O-isopropylidene-α-D-allofuranose 
• 2280-44-6 D-Glucose 

Downstream Products

• 37077-81-9 1,2-isopropylidene-α-D-ribofuranose 
• 113273-96-4 (1R,6R,8R,9R)-3-(benzoyloxy)-8,9-(isopropylidenedioxy)-7-oxabicyclo<4.3.0>nonane 
• 1104739-11-8 (5R)-1,2-O-isopropylidene-5-phenyl-α-D-ribofuranose 
• 1104739-10-7 (5S)-1,2-O-isopropylidene-5-phenyl-α-D-ribofuranose 
• 1322748-56-0 N-benzyl-1,2-O-isopropylidene-3,5-dideoxy-3,5-imino-α-D-xylofuranose 
• 1338054-35-5 N-(p-methoxybenzyl)-1,2-O-isopropylidene-3,5-dideoxy-3,5-imino-α-D-xylofuranose 
• 1322748-58-2 N-benzyl-1,3-dideoxy-1,3-imino-L-xylitol 
• 1338054-42-4 N-(p-methoxybenzyl)-1,3-dideoxy-1,3-imino-L-xylitol 
• 69350-76-1 methyl 2,3,5-tri-O-benzoyl-αβ-D-ribofuranoside 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 3180-76-5 2',3',5'-tri-O-benzoyluridine 
• 1824-96-0 methyl ribofuranoside 
• 1053649-58-3 Benzoic acid (3aR,5R,6R,6aR)-5-iodoethynyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 
• 214038-41-2 Benzoic acid (3aR,5R,6R,6aR)-5-bromoethynyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 

Relevant academic research and scientific papers

Selective Wittig olefination in aqueous media for the rapid preparation of unsaturated 7,3-lactone-α-d-xylofuranose derivatives

A highly efficient and rapid protocol for the preparation of the title compounds 1a and 1b from d-glucose derivatives 2a and 2b, respectively, is reported. To this end, highly selective Wittig olefination in aqueous media was developed for the elaboration

Larger laboratory scale synthesis of 5-methyluridine and formal synthesis of its L-enantiomer

A larger laboratory scale synthesis (>60 g per run) of 5-methyluridine is presented. The critical intermediate 1,2-O-isopropylidene-α-D-ribofuranose was prepared from very cheap D-glucose via D-allose. Its L-enantiomer was obtained from L-arabinose via L-glucose, and also from L-xylose. {figure presented}.

Chemical preparation method of ribose oxime

The invention relates to a chemical preparation method of ribose oxime. The method is characterized in that the method comprises the following steps: preparing a reaction system by using isopropylidene-alpha-D-allofuranose, sodium bicarbonate and distilled water, adding sodium periodate, and reacting at a certain temperature to obtain an oxidation degradation product; carrying out a heating refluxing reaction on a methanol solution of methoxamine and the oxidation degradation product to obtain an oxime protection material; and reacting the oxime protection material and dichlorodicynobenzoquinone with an acetonitrile-water solution, adding a sodium borohydride solution, reacting, removing isopropylidene groups, and carrying out ether recrystallization to obtain the ribose oxime.

Inhibition of nonmammalian glycosidases by azetidine iminosugars derived from stable 3,5-Di-O-triflates of pentoses

Efficient ring closure of stable crystalline 3,5-di-O-triflates of pentofuranosides with amines to form azetidines allowed preliminary evaluation of four-ring iminosugars as glycosidase inhibitors; significant and specific inhibition of nonmammalian α-glucosidases is shown by l-xylo- and l-arabino-iminosugar azetidines.

Inverse stereoselectivity in the nucleophilic attack on five-membered ring oxocarbenium ions. Application to the total synthesis of 7-epi-(+)-goniofufurone

A highly stereoselective nucleophilic substitution at the anomeric position of 1,2-O-isopropylidene furanose derivatives was employed for the synthesis of 7-epi-(+)-goniofufurone and two of its stereoisomers. According to Woerpel's model, the stereoselect

Sugar-modified conjugated diene analogues of adenosine and uridine: Synthesis, interaction with S-adenosyl-L-homocysteine hydrolase, and antiviral and cytostatic effects

Moffatt oxidation of 2′,3′-O-isopropylideneuridine (1a) and treatment of the crude 5′-aldehyde with formylmethylene-stabilized Wittig reagent gave the vinylogously extended 7′-aldehyde 2a. Condensation of 2a with ethoxycarbonyl- or dibromomethylene phosph

Diastereospecific chemical synthesis of ribonucleosides-3',4',5',5'-D4

The diastereospecific chemical syntheses of uridine-3',4',5',5'-d4, cytidine-3',4',5',5'-d4, adenosine-3',4',5',5'-d4 and guanosine- 3',4',5',5'-d4 (>97 atom % 2H at C3', C4' and C5') have been achieved by condensation of appropriately protected aglycone with 1-O-acetyl 2,3,5-tri- O-(4-toluoyl)-α/β-D-ribofuranose-3,4,5,5'-d4 (27), which has been obtained in an overall yield of 20 % in 11 steps starting from 50 mmol of 2:5,6-Di-O- isopropylidene-α-D-glucose.

Synthesis of racemic ribose from D-glucose

Racemic ribose is a valuable starting material for investigations of the origins of biomolecular homochirality. It can be synthesized in seven steps starting from D-glucose.

Inactivation of S-adenosyl-L-homocysteine hydrolase and antiviral activity with 5',5',6',6'-tetradehydro-6'-deoxy-6'-halohomoadenosine analogues (4'-haloacetylene analogues derived from adenosine)

Treatment of a protected 9-(5,6-dideoxy-β-D-ribo-hex-5- ynofuranosyl)adenine derivative with silver nitrate and N-iodosuccinimide (NIS) and deprotection gave the 6'-iodo acetylenic nucleoside analogue 3c. Halogenation of 3-O-benzoyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-ribo-hex- 5-enofuranose gave 6-halo acetylenic sugars that were converted to anomeric 1,2-di-O-acetyl derivatives and coupled with 6-N-benzoyladenine. These intermediates were deprotected to give the 6'-chloro 3a, 6'-bromo 3b, and 6'- iodo 3c acetylenic nucleoside analogues. Iodo compound 3c appears to inactivate S-adenosyl-L-homocysteine hydrolase by a type I ('cofactor depletion') mechanism since complete reduction of enzyme-bound NAD+ to NADH was observed and no release of adenine or iodide ion was detected. In contrast, incubation of the enzyme with the chloro 3a or bromo 3b analogues resulted in release of Cl- or Br- and Ade, as well as partial reduction of E-NAD+ to E-NADH. Compounds 3a, 3b, and 3c were inhibitory to replication of vaccinia virus, vesicular stomatitis virus, parainfluenza-3 virus, and reovirus-1 (3a 3b 3c, in order of increasing activity). The antiviral effects appear to correlate with type I mechanism-based inhibition of S- adenosyl-L-homocysteine hydrolase. Mechanistic considerations are discussed.