32453-67-1

Upstream product

• 6893-65-8 1,2-di-O-isopropylidene-5-O-tosyl-D-xylofuranose 
• 532-20-7 D-xylofuranose 
• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 50600-39-0 5-deoxy-5-iodo-1,2-O-isopropylidene-alpha-D-xylofuranose 
• 4152-79-8 1,2-O-isopropylidene-5-methyl-5-deoxy-α-D-xylofuranose 

Downstream Products

• 158112-55-1 5-O-deoxy-D-ribofuranose 
• 109536-53-0 5-deoxy-1,2-isopropylidene-3-O-(p-methoxybenzyl)-α-D-ribofuranose 
• 161200-09-5 (E)-(4S,5R)-4-Allyloxy-5-formyloxy-hex-2-enoic acid 2-(toluene-4-sulfonyl)-ethyl ester 
• 69260-71-5 doxifluridine 
• 76462-82-3 1-(5-Deoxy-2,3-di-O-acetyl-β-D-ribofuranosyl)-5-fluor-uracil 
• 37076-71-4 5-deoxy-1,2,3-tri-O-acetyl-D-ribofuranose 
• 197567-50-3 (R)-3-Benzyloxy-2-[((2R,4R,5R,6R)-5-hydroxy-5,6-dimethyl-2-phenyl-[1,3]dioxane-4-carbonyl)-amino]-2-methyl-propionic acid 
• 197567-48-9 (S)-3-Benzyloxy-2-[((2R,4R,5R,6R)-5-hydroxy-5,6-dimethyl-2-phenyl-[1,3]dioxane-4-carbonyl)-amino]-2-methyl-propionic acid 
• 197567-49-0 (R)-3-Benzyloxy-2-[((2R,4R,5R,6R)-5-hydroxy-5,6-dimethyl-2-phenyl-[1,3]dioxane-4-carbonyl)-amino]-2-methyl-propionic acid methyl ester 
• 197567-47-8 (S)-3-Benzyloxy-2-[((2R,4R,5R,6R)-5-hydroxy-5,6-dimethyl-2-phenyl-[1,3]dioxane-4-carbonyl)-amino]-2-methyl-propionic acid methyl ester 
• 197567-45-6 2,4-O-benzylidene-5-deoxy-3-C-methyl-D-ribose ethylene dithioacetal 
• 197567-46-7 2,4-O-benzylidene-5-deoxy-3-C-methyl-D-ribonic acid 
• 176908-58-0 (R)-3-Benzyloxy-2-((2R,3R,4R)-2,4-bis-benzyloxy-3-methyl-pentanoylamino)-2-methyl-propionic acid 
• 176908-56-8 (S)-3-Benzyloxy-2-((2R,3R,4R)-2,4-bis-benzyloxy-3-methyl-pentanoylamino)-2-methyl-propionic acid 

Relevant academic research and scientific papers

Synthesis and Antiviral Evaluation of 3'-C-Hydroxymethyl-3'-O-Phosphonomethyl-β-D-5'-deoxyxylose Nucleosides

L-2'-deoxythreose nucleoside phosphonates PMDTA and PMDTT possess potent anti-HIV activity. Herein, a novel class of 3'-C-branched-l-threose nucleoside phosphonate analogs, 5'-deoxy-3'-C-hydroxymethyl-3'-O-phosphonomethyl-d-xylose nucleosides, were synthesized and biologically evaluated. The key sugar intermediate 3-C-benzyloxymethyl-3-O-diethylphosphonomethyl-1,2-O-isopropylidene-α-d-5-deoxyxylose (8) was firstly synthesized, which may be an interesting scaffold for access to diverse 3'-C-branched l-threosyl nucleoside phosphonate derivatives. And the key synthesis involved Wittig olefination of 1,2-O-isopropylidene-3-oxo-α-d-5-deoxyxylose, stereoselective dihydroxylation of alkenes by aqueous KMnO4, selective benzylation of hydroxymethyl group under activation of dibutyltin oxide, and introduction of phosphonate group by nucleophilic substitution. Eventually, glycosylation under Vorbrüggen conditions provided 3'-C-hydroxymethyl-3'-O-phosphonomethyl-β-d-5'-deoxyxylose nucleoside analogs in satisfying yield.

Palladium-catalyzed enantioselective allylic substitution in the presence of monodentate furanoside phosphoramidites

A library of monodentate furanoside phosphoramidites, easily synthesized from inexpensive D-xylose and optically pure 1,1-bi-2-naphthol (BINOL), was used as ligands for the palladium-catalyzed allylic alkylation and amination. The matched pair was formed from D-xylose-derivatives and (S)-BINOL. The asymmetric induction depends strongly on the substituent at the C5 of the carbohydrate backbone; both bulky 5-O-pivaloyl and 5-deoxy derivatives gave excellent results, whereas ligands with trityl protection at position C5 induced low ee values with reversal of configuration. The solvent used for the addition is also of great importance with highest enantioselectivities observed in diethyl ether. The best results for both alkylation and amination, up to 98-99 ee, were obtained for sterically demanding allylic acetates. Single is better: New carbohydrate ligands bearing a single 1,1-bi-2-naphthol (BINOL)-derived phosphoramidite moiety are developed and successfully applied to the palladium-catalyzed asymmetric allylic substitution. The enantioselectivities are equal or better than those obtained for similar systems containing two BINOL moieties and reach up to 99 ee.

Total synthesis of (-)-Pramanicin

The total synthesis of natural (-)-pramanicin, a highly oxygenated γlactam-type antifungal agent, is described. The enantiospecific total synthesis of this natural product commenced with 5-deoxy-1,2-O-isopropylidene-α-d-xylofuranose as an enantiopure star

Synthesis of conagenin analogs modified at 3'-carbon atom

Three conagenin analogs modified at 3'-carbon centre and their diastereoisomers at position C-2 mere synthesized. The synthesis of the acylating carboxylic acids 13, 22 and 33 having stereotriads were elaborated starling from D-xylose performing stereoselective reactions.

The first synthesis and determination of absolute stereochemistry of clonostachydiol - Part II

The first total synthesis of clonostachydiol has been achieved from two appropriately protected hydroxy acids that are derived from (D)-xylose and 1,2-O-isopropylidene (D)-glyceraldehyde.This synthesis has proved the absolute configuration of four stereoc

The Photochemistry of Ketones Derived from Carbohydrates. Part 10. A Study of Stereochemical Influences on Photo-induced Rearrangements and Ring Expansions of 3-Oxacyclopentanones Using 1,2-O-Isopropylidenefuranos-3-ulose Derivatives

U.v.-irradiation of the 3-oxacyclopentanone 5-deoxy-1,2-O-isopropylidene-β-D-threo-pentofuranos-3-ulose (9) in methanol gave at -60 deg C, and to a small extent at +20 deg C, -2,3-isopropylidenedioxy-5-methoxy-6-methyl-1,4-dioxane (12), whereas in a benzene solution at +20 deg C only the unsaturated lactones 2,2-dimethyl-5--1,3-dioxolan-4-one (13) and its (E)-isomer (14) were obtained.The photoproducts formed from (9) in methanol-diethyl ether (1:4) at -60 deg C were a mixture of the dioxane (12) and the lactones (13) and (14).The isomeric erythro-ulose (20) gave only the lactones (13) and (14) when irradiated in either methanol-diethyl ether (1:4) at -60 deg C or in benzene at +20 deg C.The lactone mixtures from (9) and (20) possessed similar specific optical rotations.U.V.-irradiation of a benzene solution of 1,2-O-isopropylidene-α-L-glycero-tetrofuranos-3-ulose (22) at +20 deg C gave racemic 5-ethenyloxy-2,2-dimethyl-1,3-dioxolan-4-one (16).The optical activity exhibited by the lactone mixtures produced from ketones (9), (20) and (22) indicated that they were not formed via the respective oxacarbenes (11), (29) and (30), which are chiral, but through the intermediacy of the symmetric enals (31) from (9) and (20), and (32) from (22).The uloses (9) and (20) formed hemiacetals (18), and (23) and (24) respectively, in methanolic solutions but only to a limited extent at low temperatures.