6605-29-4

Usage

Uses

Used in Organic Synthesis:
Methyl 4,6-Di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside is used as a key intermediate in the synthesis of various complex organic molecules. Its unique structure allows for a range of chemical reactions, such as esterification, acetylation, and glycosylation, which can be employed to create a diverse array of compounds with potential applications in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Methyl 4,6-Di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside is used as a building block for the development of novel drug candidates. Its ability to be modified and incorporated into other molecules makes it a valuable asset in the design and synthesis of new drugs with potential therapeutic properties.
Used in Chemical Research:
Methyl 4,6-Di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside is also used in chemical research to study the properties and reactivity of complex organic molecules. Researchers can use Methyl 4,6-Di-O-acetyl-2,3-dideoxy-a-D-threo-hex-2-enopyranoside to explore new reaction pathways, develop innovative synthetic methods, and gain a deeper understanding of the underlying chemical principles governing the behavior of similar compounds.
Used in Material Science:
In the field of material science, Methyl 4,6-Di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside can be used to develop new materials with unique properties. By incorporating Methyl 4,6-Di-O-acetyl-2,3-dideoxy-a-D-threo-hex-2-enopyranoside into the molecular structure of various materials, researchers can potentially create new polymers, coatings, or other materials with enhanced properties, such as improved strength, durability, or biocompatibility.

Upstream product

• 67-56-1 methanol 
• 52485-06-0 3,4,6-tri-O-acetyl-D-glucal 
• 4098-06-0 triacetyl-D-galactal 
• 2873-29-2 Acetic acid (2S,3S,4S)-4-acetoxy-2-acetoxymethyl-3,4-dihydro-2H-pyran-3-yl ester 
• 2873-29-2 Acetic acid (2R,3S,4R)-4-acetoxy-2-acetoxymethyl-3,4-dihydro-2H-pyran-3-yl ester 
• 286410-13-7 phenyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-1-thio-hex-2-enopyranoside 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 2280-44-6 D-Glucose 
• 2873-29-2 D-glucal triacetate 
• 149-73-5 trimethyl orthoformate 
• 6586-65-8 3,4,6-tri-O-acetyl-D-galactal 

Downstream Products

• 6605-38-5 methyl 4,6-di-O-benzoyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside 
• 1053182-38-9 methyl 4,6-di-O-benzyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside 
• 1310543-00-0 C₂₀H₂₃NO₆ 
• 64551-84-4 methyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hexopyranoside 
• 93220-64-5 Methyl-4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranosid 
• 940933-70-0 (2R,4aR,6S,8aS)-2-phenyl-6-(propa-1,2-dienyloxy)hexahydropyrano[3,2-d][1,3]dioxine 
• 528584-71-6 (2S)-3-hydroxy-2-methoxycarbonyl-2H-pyran 

Relevant academic research and scientific papers

Regio- And diastereoselective Pd-catalyzed synthesis of C2-aryl glycosides

An efficient regio- and diastereoselective arylation method of readily available 2,3-glycals with various aryl iodides has been established. Using the Pd(OAc)2/AsPh3 precatalytic system, this protocol proved to be general to prepare a variety of substituted C2-aryl glycosides in good yields with complete diastereoselectivity.

Selective Synthesis of Some Aminosugars via Catalytic Aminohydroxylation of Protected 2,3-Unsaturated d -Gluco- And d -Galacto-2-hexenopyranosides

The aminohydroxylation of methyl 4,6-di-O-(tert-butyldimethylsilyl)-2,3-unsaturated α-d-glucopyranoside proceeds in the presence of chloramine-T, OsO4 (4 mol %), (DHQ)2PHAL (5 mol %), and triethylbenzylammonium chloride (TEBAC) in both a stereoselective a

Montmorillonite-catalyzed glysosylation of alcohols with glycals derived from galactose and glucose under microwave-induced reactions

Montmorillonite K10-catalyzed glycosylation of alcohols with glycals obtained from galactose and glucose is performed efficiently using microwave irradiation with good anomeric selectivity.

Selective Synthesis of Partially Protected d -Talopyranosides and d -Gulopyranosides via Catalytic Asymmetric Dihydroxylation: Multiplier Effects of Substrate Control and Catalyst Control

Highly selective syntheses of d-talopyranosides and d-gulopyranosides have been achieved by utilizing the multiplier effects of substrate control and catalyst control. Through the combination of an O-benzoyl-protected substrate and the AD-mix-β system, the d-talopyranoside was obtained in a ratio of 96:4. In contrast, the d-gulopyranoside was obtained in a ratio of 3:97 through the use of an O-tert-butyldimethylsilyl-protected substrate and AD-mix-α.

Synthesis of paclitaxel. 1. synthesis of the abc ring of paclitaxel by SmI2-mediated cyclization

A convergent synthesis of the ABC ring of antitumor natural product paclitaxel (Taxol) is described. SmI2-mediated reductive cyclization of an allylic benzoate possessing an aldehyde function, synthesized from tri-O-acetyl-d-glucal and 1,3-cyclohexanedione, smoothly afforded the highly strained 6-8-6 tricarbocyclic structure in 66% yield.

Ruthenium Catalyzed Stereo/Chemo/Regioselective One-Pot Synthesis of C(2)-C(3) Unsaturated and α-d-Mannopyranosyl Sulfones

An efficient and divergent approach to C(2)-C(3) unsaturated glycosyl and α-d-mannopyranosyl sulfones has been developed via ruthenium-promoted direct glycosylation, oxidation, and dihydroxylation from glycal in one-pot. The presence of stoichiometric amounts of NaIO4 and in situ generation of RuO4 from a RuCl3-NaIO4 reagent system were crucial for chemoselective oxidation of sulfide in the presence of an olefin moiety. The dual-role of ruthenium in sequential glycosylation-oxidation-dihydroxylation is amenable to a wide range of thio acceptors to access α-d-mannopyranosyl sulfones in good yields with high regioselectivity.

Linearization of carbohydrate derived polycyclic frameworks

We report easy access to carbohydrate derived diverse tricyclic skeletons which could be beneficial for exploring polyfunctionalized chiral alicycles. The key reaction to assemble a sugar fused tricyclic core is intermolecular tandem esterification and 1,3-dipolar cycloaddition. The framework was elaborated using amide forming reactions, opening of isoxazolidine rings followed by N and O-acylations. The sequences provide distinct, spatially separated and encoded chemical entities that may pave the way to investigate cell functions.

Stereoselective synthesis of pseudoglycosides catalyzed by TeCl4 under mild conditions

Catalytic amounts of tellurium(IV) tetrachloride were used to promote the O-glycosylation of 3,4,6-tri-O-acetyl-d-glucal to give the corresponding 2,3-unsaturated-O-glycosides. With simple alcohols, the desired compounds were obtained in good yields and excellent anomeric selectivity in a short reaction time using only 2 mol % of the catalyst. The application of the method in the synthesis of a small set of glycopyranosides with rigid or flexible linkers gave the corresponding α anomers as products in good yields. Further applications of some of the synthesized compounds in allylation reaction of aldehydes gave the corresponding homoallylic alcohols in good yields.

Stereoselective synthesis of pseudoglycosides catalyzed by TeCl4 under mild conditions

Catalytic amounts of tellurium(IV) tetrachloride were used to promote the O-glycosylation of 3,4,6-tri-O-acetyl-d-glucal to give the corresponding 2,3-unsaturated-O-glycosides. With simple alcohols, the desired compounds were obtained in good yields and excellent anomeric selectivity in a short reaction time using only 2 mol % of the catalyst. The application of the method in the synthesis of a small set of glycopyranosides with rigid or flexible linkers gave the corresponding α anomers as products in good yields. Further applications of some of the synthesized compounds in allylation reaction of aldehydes gave the corresponding homoallylic alcohols in good yields.

Iron(III) triflate, a new efficient catalyst for Type i Ferrier Rearrangement

By using iron(III) triflate as catalyst, an improved method for the synthesis of 2,3-unsaturated-O-glycosides has been established. A series of 2,3-unsaturated-O-glucosides were obtained from 2,4,6-tri-O-acetyl-d-glucal in good yield and high anomeric selectivity.