3169-98-0

Usage

General Description

Alpha-D-erythro-Hex-2-enopyranoside, methyl 2,3-dideoxy-4,6-O-(phenylmethylene)- is a complex chemical compound commonly used in organic synthesis and pharmaceutical research. It is a derivative of the sugar molecule, specifically a hexose, and is commonly used as a starting material for the synthesis of various biologically active compounds. It is widely used in the development of new drugs, as well as in studies related to carbohydrate chemistry and biochemistry. Its unique structure and properties make it a valuable tool in research and development in the field of pharmaceuticals and organic chemistry.

InChI:InChI=1/C14H16O4/c1-15-13-8-7-11-12(17-13)9-16-14(18-11)10-5-3-2-4-6-10/h2-8,11-14H,9H2,1H3

Upstream product

• 4234-42-8 methyl 4,6-O-benzylidene-2-O-p-toluenesulphonyl-α-D-ribohexopyranosid-3-ulose 
• 75251-54-6 Methyl-4,6-O-benzyliden-3-desoxy-3-iod-2-O-tetrahydropyranyl-α-D-altropyranosid 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 13265-84-4 D-glucal 
• 201230-82-2 carbon monoxide 
• 197570-60-8 Trifluoro-methanesulfonic acid (4aR,6S,8aR)-6-methoxy-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 
• 4148-58-7 (4aR,6S,7S,8R,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 
• 22860-25-9 methyl 2,3-dideoxy-4,6-dihydroxy-α-D-erythro-hex-2-enopyranoside 
• 618-31-5 benzylidene dibromide 
• 67-56-1 methanol 
• 120679-81-4 4,6-O-benzylidene-3-O-(allylthioacetyl)-D-allal 
• 2880-96-8 (1aR,2S,6R,7aR,7bR)-2-Methoxy-6-phenyl-hexahydro-1,3,5,7-tetraoxa-cyclopropa[a]naphthalene 
• 56981-10-3 Methyl-4,6-O-benzyliden-3-desoxy-3-iod-α-D-altropyranosid 
• 5987-33-7 4,6-O-benzylidene-D-allal 

Downstream Products

• 16848-76-3 methyl 4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hexopyranoside 
• 343930-11-0 6-Methoxy-3,6-dihydro-2H-pyran-2-carbaldehyde 
• 23110-90-9 6-O-benzoyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 
• 343930-10-9 Benzoic acid (2R,3S,6S)-3-methanesulfonyloxy-6-methoxy-3,6-dihydro-2H-pyran-2-ylmethyl ester 
• 57458-26-1 [3S-⁽²⁾H]-4,6-O-benzylidene-3-deoxy-D-glucal 
• 799804-65-2 1-(methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-altropyranosid-2-yl)-4-phenyl-but-3-yn-2-one 
• 799804-64-1 1-(methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-altropyranosid-2-yl)4-phenylbut-3-yn-2-ol 
• 593280-25-2 2-(methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-altropyranosid-2-yl)ethanal 
• 131529-43-6 methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-(prop-2-enyl)-α-D-altropyranoside 

Relevant academic research and scientific papers

Enyne metathesis on prop-2-ynyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosides

The enyne metathesis on differently functionalized prop-2-ynyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosides (1, 2 and 3) has been analyzed for the first time, and the new and interesting results are described here.

Transition state analysis of thymidine hydrolysis by human thymidine phosphorylase

Human thymidine phosphorylase (hTP) is responsible for thymidine (dT) homeostasis, and its action promotes angiogenesis. In the absence of phosphate, hTP catalyzes a slow hydrolytic depyrimidination of dT yielding thymine and 2-deoxyribose (dRib). Its transition state was characterized using multiple kinetic isotope effect (KIE) measurements. Isotopically enriched thymidines were synthesized enzymatically from glucose or (deoxy)ribose, and intrinsic KIEs were used to interpret the transition state structure. KIEs from [1′- 14C]-, [1-15N]-, [1′-3H]-, [2′R-3H]-, [2′S-3H]-, [4′- 3H]-, and [5′-3H]dTs provided values of 1.033 ± 0.002, 1.004 ± 0.002, 1.325 ± 0.003, 1.101 ± 0.004, 1.087 ± 0.005, 1.040 ± 0.003, and 1.033 ± 0.003, respectively. Transition state analysis revealed a stepwise mechanism with a 2-deoxyribocation formed early and a higher energetic barrier for nucleophilic attack of a water molecule on the high energy intermediate. An equilibrium exists between the deoxyribocation and reactants prior to the irreversible nucleophilic attack by water. The results establish activation of the thymine leaving group without requirement for phosphate. A transition state constrained to match the intrinsic KIEs was found using density functional theory. An active site histidine (His116) is implicated as the catalytic base for activation of the water nucleophile at the rate-limiting transition state. The distance between the water nucleophile and the anomeric carbon (rC-O) is predicted to be 2.3 A at the transition state. The transition state model predicts that deoxyribose adopts a mild 3′-endo conformation during nucleophilic capture. These results differ from the concerted bimolecular mechanism reported for the arsenolytic reaction (Birck, M. R.; Schramm, V. L. J. Am. Chem. Soc. 2004, 126, 2447-2453).

Radical deoxygenation of alcohols and intermolecular carbon-carbon bond formation with surfactant-type radical chain carriers in water

An efficient and mild method is developed for radical deoxygenation of alcohols and formation of carbon-carbon bonds in water without adding additives such as surfactants. The reaction was applied to synthesis of 2′,3′-didehydro-2′,3′-dideoxynucleosides that are potent anti-HIV agents. The reaction afforded environmentally benign reaction conditions.

TRANSACETALISATION PROCESS

The invention relates to the resolution of racemic mixtures, and in particular to the separation of enantiomers of chiral alcohols utilising recyclable chiral auxiliaries. The present invention also relates to a process for preparing these recyclable chiral auxiliaries using an enantiomerically pure alcohol.

Radical deoxygenation of alcohols and vicinal diols with N-ethylpiperidine hypophosphite in water

Radical deoxygenation of alcohols and vicinal diols with N-ethylpiperidine hypophosphite both in alcohols and in water is described. S-Methyl dithiocarbonate and bis-S-methyl dithiocarbonate of carbohydrates and nucleosides were deoxygenated efficiently under reaction conditions.

Total synthesis of S-(+)-argentilactone

Asymmetric total synthesis of S-(+)-argentilactone (2) was accomplished, using methyl-α-D-glucopyranoside (3) as carbohydrate template. Benzylidene acetal 5 was hydrolysed with tBuOOH/AlCl3 and further manipulated to produce the alde

An expeditious methodology for the incorporation of unsaturated systems into carbohydrates via an enol triflate

One step synthesis of enal, diane, divinyl ketone and enyne systems on a carbohydrate template via an enol triflate.

Alkenes from Cyclic Sulfates and Thionocarbonates of 1,2-Diols via Tellurium Chemistry

Treatment of 1,2-diol cyclic sulfates (1,3,2-dioxathiolane 2,2-dioxides) with telluride ion, generated in situ by reduction of the element, yields alkenes rapidly (10 min - 2 h) under mild conditions (0 deg C to room temperature).The reaction is stereospecific, e. g. meso-2,3-diphenylethane-2,3-diol -> cis-stilbene; d,l-2,3-diphenylethane-2,3-diol -> trans-stilbene.Unsaturated mannose and ribose derivatives have been obtained, and diethyl (-)-tartrate gives diethyl fumarate.The reaction may be performed with 0,1 equiv or less of elemental tellurium in the presence of a stoichiometric amount of reducing agent.Reaction of telluride ion with cyclic thionocarbonates (1,3-dioxolane-2-thiones) of meso- and d,l-1,2-diphenylethane-1,2-diol yields cis- and trans-stilbene, respectively.

Selective generation of free radicals from epoxides using a transition-metal radical. A powerful new tool for organic synthesis

Bis(cyclopentadienyl)titanium(III) chloride reacts with epoxides by initial C-O homolysis. The regiochemistry of the opening is determined by the relative stabilities of the radicals. Depending on the reaction partners, these radicals undergo intramolecular (hex-5-enyl cyclization) or intermolecular additions to olefins. The resultant radicals are efficiently scavenged by a second equivalent of Ti(III) to afford the corresponding Ti(IV) derivative. Treatment of this intermediate with electrophiles such as H+ or halogens provides a route to functionalized cyclopentanes and other useful products. The radical initially formed from an epoxide can also be trapped by H-atom donors such as 1,4-cyclohexadiene or tert-butyl thiol, resulting in an overall reduction of the epoxide. In the absence of a H-atom donor or an olefin, this radical is trapped by Ti(III), resulting in a β-oxido-Ti organometallic species which undergoes facile elimination to give an olefin. The reaction conditions are remarkably mild and are applicable to very sensitive substrates.

The invention of radical reactions. Part XXXI. Diphenylsilane: A reagent for deoxygenation of alcohols via their thiocarbonyl derivatives, deamination via isonitriles, and dehalogenation of bromo- and iodo- compounds by radical chain chemistry

Various thionocarbonates and xanthates of alcohols and bis-xanthates of vic-diols are readily deoxygenated to the corresponding hydrocarbons or olefins, while bromides and iodides are dehalogenated with diphenylphenylsilane in good yield.