18031-51-1

Usage

Uses

Used in Organic Synthesis:
Methyl 2,3,6-Tri-O-acetyl-α-D-glucopyranoside is used as a key intermediate in organic synthesis for the preparation of various complex organic molecules. Its unique structure allows for selective reactions and modifications, making it a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Methyl 2,3,6-Tri-O-acetyl-α-D-glucopyranoside is used as a starting material for the synthesis of glycosides and other carbohydrate-based drugs. Its ability to form stable glycosidic linkages with various aglycones makes it an essential component in the development of new therapeutic agents with improved pharmacokinetic properties.
Used in Agrochemical Industry:
Methyl 2,3,6-Tri-O-acetyl-α-D-glucopyranoside is also utilized in the agrochemical industry for the synthesis of glycosylated pesticides and other bioactive compounds. The introduction of carbohydrate moieties can enhance the solubility, stability, and bioavailability of these agrochemicals, leading to more effective and environmentally friendly products.
Used in Specialty Chemicals:
In the specialty chemicals sector, Methyl 2,3,6-Tri-O-acetyl-α-D-glucopyranoside is employed as a precursor for the synthesis of various functional materials, such as surfactants, polymers, and coatings. Its unique chemical properties enable the development of innovative products with tailored properties for specific applications.

Upstream product

• 29868-42-6 methyl 2,3-di-O-acetyl-α-D-glucopyranoside 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 7432-72-6 methyl 2,3,4-tri-O-acetyl-α-D-glucopyranose 
• 131000-31-2 methyl 2,3,4-tri-O-acetyl-6-O-formyl-α-D-glucopyranoside 
• 81712-51-8 methyl 2,3,6-tri-O-acetyl-4-O-diphenylmethyl-α-D-glucopyranoside 
• 108-24-7 acetic anhydride 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 75-36-5 acetyl chloride 
• 604-70-6 Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yl ester 
• 7511-40-2 methyl 2,3,4-tri-O-acetyl-6-O-trityl-α-D-glucopyranoside 
• 850848-12-3 methyl 2,3,4-tri-3-O-acetyl-6-O-[2-(prenyloxymethyl)benzoyl]-α-D-glucopyranoside 
• 56-35-9 bis(tri-n-butyltin)oxide 
• 131021-83-5 methyl 6-O-formyl-α-D-glucopyranoside 
• 428500-98-5 methyl 2,3,4-tri-O-acetyl-6-O-[(2-azidomethyl)phenylacetyl]-α-D-glucopyranoside 

Downstream Products

• 139710-67-1 methyl-2,3,6-tri-O-acetyl-4-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glucopyranosyl)-α-D-glucopyranoside 
• 130052-62-9 methyl-2,3,4-tri-O-acetyl-6-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glucopyranosyl)-α-D-glucopyranoside 
• 81712-51-8 methyl 2,3,6-tri-O-acetyl-4-O-diphenylmethyl-α-D-glucopyranoside 
• 983-79-9 benzophenone azine 
• 32934-08-0 methyl 2,3,6-tri-O-acetyl-4-deoxy-4-fluoro-α-D-galactopyranoside 
• 365418-30-0 methyl (4S)-2,3,6-tri-O-benzyl-4-deoxy-4-(2-ethanal)-α-D-glucopyranoside 
• 224324-88-3 methyl (4S)-2,3,6-tri-O-benzyl-4-deoxy-4-(2-ethanoic acid)-α-D-glucopyranoside 
• 557088-28-5 methyl (4R)-2,3,6-tri-O-benzyl-4-deoxy-4-(2-ethanal)-α-D-glucopyranoside 
• 365418-09-3 (2R,3S,4R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-((2S,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylmethyl)-3,4-dihydro-2H-pyran 
• 365418-07-1 methyl (4S)-2,3,6-tri-O-benzyl-4-deoxy-4-C-((3,4,6-tri-O-benzyl-1,2-dideoxy-D-arabino-hex-1-enyl)-(2-ethanoate))-α-D-glucopyranoside 
• 365418-10-6 (2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((2S,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylmethyl)-tetrahydro-pyran-3-ol 
• 365418-08-2 methyl (4S)-2,3,6-tri-O-benzyl-4-deoxy-4-C-((3,4,6-tri-O-benzyl-1,2-dideoxy-D-arabino-hex-1-enyl)-2-propene)-α-D-glucopyranoside 
• 81712-52-9 methyl 4-O-diphenylmethyl-2,3,6-tri-O-methyl-α-D-glucopyranoside 
• 1095481-08-5 methyl 2,3-di-O-benzyl-4-O,6-S-(1-cyano)benzylidene-β-D-mannopyranosyl-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranoside 

Relevant academic research and scientific papers

An improved synthesis of 4-deoxy-4-fluoro-D-galactopyranosyl derivatives

This note presents an improved synthesis of 4-deoxy-4-fluoro-D-galactopyranosyl derivatives, using a sterically unencumbered acylating agent such as acetyl chloride.

Streamlined Iterative Assembly of Thio-Oligosaccharides by Aqueous S-Glycosylation of Diverse Deoxythio Sugars

A streamlined iterative assembly of thio-oligosaccharides was developed by aqueous glycosylation. Facile syntheses of various deoxythio sugars with the sulfur on different positions from commercially available starting materials were described. These syntheses featured efficient chemical methods including our recently reported BTM-catalyzed site-selective acylation. The resulting deoxythio sugars could then be used for the Ca(OH)2-promoted protecting group-free S-glycosylation in water at room temperature. The aqueous glycosylation reaction proceeded smoothly to afford the corresponding 1,2-trans S-glycosides in good yields with high chemo- and stereoselectivity. An appropriate choice of protecting groups for the thiol in the glycosyl donor was necessary for the development of iterative synthesis of thio-oligosaccharides. The aqueous glycosylation was then applied to the synthesis of a trimannoside moiety of N-linked glycans core region.

2-(Prenyloxymethyl)benzoyl (POMB) group: a new temporary protecting group removable by intramolecular cyclization

2-(Prenyloxymethyl)benzoates can be prepared from alcohols and readily available 2-(prenyloxymethyl)benzoic acid by standard acylation techniques or by Mitsunobu reaction with inversion of configuration. The POMB group can be cleaved first by oxidative removal of the prenyl group with DDQ followed by lactonization with expulsion of the alcohol catalyzed by Yb(OTf)3. These reaction conditions are compatible with the presence of a large number of common protecting groups.

Reagent-dependent regioselective control in multiple carbohydrate esterifications

(Chemical Equation Presented) Regioselective control in organotin-mediated multiple acylation of carbohydrates is presented. The acylation reagent could be efficiently used to direct the product formation. Reagent-dependent thermodynamic and kinetic contr

Removal of acid-labile protecting groups on carbohydrates using water-tolerant and recoverable vanadyl triflate catalyst

Acetal, trityl, and TBDMS protecting groups on saccharides were subjected to alcoholysis using a catalytic amount of vanadyl triflate in an MeOH-CH 2Cl2 solvent system. The configuration at the anomeric positions of saccharides was retained, and no glycosidic bond cleavage and oxidation of sulfides were observed. The presented method was easily implemented, compatible with diverse functional groups, and regioselective in some cases.

2-(Prenyloxymethyl)benzoyl (POMB) as a new temporary protecting group for alcohols

The 2-(prenyloxymethyl)benzoyl (POMB) group was introduced in high yields to hydroxyl functions using the crystalline reagent, 2-(prenyloxymethyl)benzoic acid, in the presence of dicyclohexylcarbodiimide (DCC) and 4- dimethylaminopyridine (DMAP). 2-(Prenyloxymethyl)benzoic acid is readily available, in two steps, from phthalide in 65% overall yield. The POMB group can be cleaved, in two steps, by treatment with 2,3-dichloro-5,6-dicyanoquinone (DDQ) followed by intramolecular lactonisation of the resulting hydroxy ester induced by a catalytic amount of Yb(OTf)3·H2O. The reaction conditions are compatible with the presence of a number of protecting groups such as isopropylidene, benzyl, acetyl, chloroacetyl, benzoyl, levulinoyl, Fmoc and Boc groups.

An easy approach for the acetylation of saccharidic alcohols. Applicability for regioselective protections

Cheap 4 ? molecular sieves can promote acetylation of carbohydrate hydroxyl functions with Ac2O in absence of any co-reagent. The procedure is compatible with the presence of a variety of acid labile protecting groups and can be exploited for regioselective protections.

(2-Azidomethyl)phenylacetyl as a new, reductively cleavable protecting group for hydroxyl groups in carbohydrate synthesis

The (2-azidomethyl)phenylacetyl group (AMPA) is described as a new protecting group for carbohydrates. AMPA was introduced to carbohydrate hydroxyl groups in the presence of DCC, while its removal was conveniently achieved via Lindlar catalyst-catalyzed hydrogenation that had no influence on other protecting groups including benzyl, acyl, acetal and ketal.

Esterase-catalysed regioselective 6-deacylation of hexopyranose per-acetates, acid-catalysed rearrangement to the 4-deprotected products and conversions of these into hexose 4- and 6-sulfates

The esterase from Rhodosporidium toruloides has been used to catalyse the hydrolysis of a series of per-acetylated α-D-hexopyranoses and α-D-hexopyranosides. Per-acetylated glucose 4, mannose 6, N-acetylgalactosamine 8, galactose 10, methyl α-D-glucoside 12, methyl α-D-mannoside 14 and methyl α-D-galactoside 16 have been selectively cleaved at the C-6 position by the esterase to give the 6-OH derivatives 5, 7, 9, 11, 13, 15 and 17. Acid-catalysed rearrangement of acetates 5, 7, 13, 15, 11, 17 and 9 with 4→6 acetyl migration gives the corresponding 4-deprotected derivatives 22-28, respectively. Hydrolyses of β-D-glucose pentaacetate 20 and α-D-lactose octaacetate 21 have been attempted, but no hydrolyses have been observed. 1,2,3,6-TetraacyIated α-D-hexopyranoses 3 and 22, derivatives of N-acetylglucosamine and glucose respectively, and 2,3,6-triacetylated α-D-hexopyranosides 24 and 25, derivatives of glucose and mannose, respectively, have been hydrolysed by the esterase to the corresponding 4,6-dihydroxy acetates 29, 18, 30 and 31. Acylation of methyl α-D-glucopyranoside 32 catalysed by the esterase provides the C-6 monoacetate 33 and the C-3 monoacetate 34 in 4 and 5% yield, respectively. The sodium salts of N-acetylglucosamine, glucose, N-acetylgalactosamine, galactose and mannose 6-sulfates 38-42, respectively, are prepared in two steps from the 6-deacetylated hexopyranoses 2, 5, 9, 11 and 7, respectively. The sodium salts of N-acetylglucosamine, glucose and mannose 4-sulfates 43-45, respectively, are prepared in two steps from the 4-deacetylated precursors 3, 22 and 26 which are obtained via acid catalysed 4→6 acyl migration of compounds 2, 5 and 7.

Fluorosugar derivatives of macrolides

Macrolides of formula (I) and methods of treatment of resistance to transplantation, fungal infections and autoimmune diseases such as rheumatoid arthritis and psoriasis using said macrolides of formula (I), STR1 wherein n is 1 or 2; A and B are taken together and form =O or A and B are taken separately and are each OH or A is OH and B is H; R1 is a fluoroglycosyl group; R2 is OH or a fluoroglycosyloxy group; and R3 is an alkyl or allyl group.