7432-72-6

Usage

Uses

Used in Organic Synthesis:
Methyl 2,3,4-triacetate-alpha-D-glucopyranoside is used as a building block for the creation of other organic compounds, particularly in the field of organic synthesis. Its unique structure allows for the development of various chemical reactions and the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Methyl 2,3,4-triacetate-alpha-D-glucopyranoside is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its ability to form esters and its reactivity make it a valuable component in the development of new drugs and medicinal agents.
Used in Flavor and Fragrance Industry:
Methyl 2,3,4-triacetate-alpha-D-glucopyranoside is used as a flavoring agent and fragrance ingredient in the food and cosmetics industries. Its fruity odor and compatibility with other ingredients make it a popular choice for enhancing the sensory properties of various products.
Used in Research and Development:
In the field of research and development, Methyl 2,3,4-triacetate-alpha-D-glucopyranoside is used as a model compound for studying the properties and reactions of esters and other organic compounds. Its unique structure and reactivity provide valuable insights into the behavior of similar compounds and contribute to the advancement of scientific knowledge.

InChI:InChI=1/C13H20O9/c1-6(15)19-10-9(5-14)22-13(18-4)12(21-8(3)17)11(10)20-7(2)16/h9-14H,5H2,1-4H3/t9-,10-,11+,12-,13?/m1/s1

Upstream product

• 155049-45-9 methyl-2,3,4-tri-O-acetyl-6-deoxy-α-D-luxo-hex-5-enopyranoside 
• 81712-50-7 methyl 2,3,4-tri-O-acetyl-6-O-diphenylmethyl-α-D-glucopyranoside 
• 850848-12-3 methyl 2,3,4-tri-3-O-acetyl-6-O-[2-(prenyloxymethyl)benzoyl]-α-D-glucopyranoside 
• 7511-40-2 methyl 2,3,4-tri-O-acetyl-6-O-trityl-α-D-glucopyranoside 
• 67-56-1 methanol 
• 3396-99-4 methyl α-D-galactopyranoside 
• 108-24-7 acetic anhydride 
• 67298-15-1 dapiramicin A 
• 51023-63-3 methyl-α,β-D-mannopyranoside 
• 181480-80-8 6-O-tert-butyldimethylsilanyl-1-O-methyl-α-D-galactopyranoside 
• 594841-23-3 Acetic acid (2R,3S,4S,5R,6S)-3,5-diacetoxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-methoxy-tetrahydro-pyran-4-yl ester 
• 5019-22-7 methyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside 
• 290359-93-2 (2R,3R,4S,5R,6S)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-6-methoxy-tetrahydro-pyran-3,4,5-triol 
• 18311-26-7 methyl 6-O-triphenylmethyl-α-D-galactopyranoside 

Downstream Products

• 1372204-42-6 methyl 6-deoxy-6-(4-(5-trifluoromethyl-2(1H)-pyridone-1-yl)-anilino)-α-D-mannopyranoside 
• 1372204-43-7 methyl 6-deoxy-6-(3-chloro-4-(5-trifluoromethyl-2(1H)-pyridone-1-yl)-anilino)-α-D-mannopyranoside 
• 1372204-44-8 methyl 6-deoxy-6-(3-(5-trifluoromethyl-2(1H)-pyridone-1-yl-methyl)-anilino)-α-D-mannopyranoside 
• 1372204-46-0 methyl 6-deoxy-6-(4-(5-trifluoromethyl-2(1H)-pyridone-1-yl-methyl)-anilino)-α-D-mannopyranoside 
• 1372204-48-2 methyl 6-deoxy-6-(2-(5-trifluoromethyl-2(1H)-pyridone-1-yl-methyl)-anilino)-α-D-mannopyranoside 
• 122119-25-9 methyl-[O²,O³,O⁴-triacetyl-O⁶-(4-phenylazo-phenylcarbamoyl)-α-D-glucopyranoside] 
• 122240-39-5 methyl-[O²,O³,O⁴-triacetyl-O⁶-(tri-O-acetyl-2-benzoylamino-2-deoxy-β-D-glucopyranosyl)-α-D-glucopyranoside] 
• 4201-69-8 methyl-(O²,O³,O⁴-triacetyl-O⁶-phenylcarbamoyl-α-D-glucopyranoside) 

Relevant academic research and scientific papers

Discriminating non-ylidic carbon-sulfur bond cleavages of sulfonium ylides for alkylation and arylation reactions

A sulfonium ylide participated alkylation and arylation under transition-metal free conditions is described. The disparate reaction pattern allowed the separate activation of non-ylidic S-alkyl and S-aryl bond. Under acidic conditions, sulfonium ylides serve as alkyl cation precursors which facilitate the alkylations. While under alkaline conditions, cleavage of non-ylidic S-aryl bond produces O-arylated compounds efficiently. The robustness of the protocols were established by the excellent compatibility of wide variety of substrates including carbohydrates.

Zirconium-Catalyzed Hydroalumination of C=O Bonds: Site-Selective De- O-acetylation of Peracetylated Compounds and Mechanistic Insights

An unprecedented hydroalumination of C = O bonds catalyzed by zirconocene dichloride is reported herein and applied to the site-selective deprotection of peracetylated functional substrates. A mixed metal hydride, with 1:1 zirconium/aluminum stoichiometry

Regio- A nd chemoselective deprotection of primary acetates by zirconium hydrides

A combination of DIBAL-H and Cp2ZrCl2 is shown to promote the regioselective cleavage of primary acetates on a broad scope of substrates, ranging from carbohydrates to terpene derivatives, with a high tolerance toward protecting groups and numerous functionalities found in natural products and bioactive compounds. Apart from providing highly valuable building blocks in only two steps from biosourced raw materials, this selective de-O-acetylation should also be strongly helpful to solve selectivity issues in organic synthesis.

MACROCYCLIC MCL-1 INHIBITORS AND METHODS OF USE

The present disclosure provides for compounds of Formula (I) wherein A2, A3, A4, A6, A7, A8, A15, RA, R5, R9, R10A, R10B, R11, R12, R13, R14, R16, W, X, and Y have any of the values defined in the specification, and pharmaceutically acceptable salts thereof, that are useful as agents in the treatment of diseases and conditions, including cancer. Also provided are pharmaceutical compositions comprising compounds of Formula (I).

Visible-Light-Mediated, Chemo- and Stereoselective Radical Process for the Synthesis of C-Glycoamino Acids

An approach for efficient synthesis of C-glycosyl amino acids is described. Different from typical photoredox-catalyzed reactions of imines, the new process follows a pathway in which α-imino esters serve as electrophiles in chemoselective addition reactions with nucleophilic glycosyl radicals. The process is highlighted by the mild nature of the reaction conditions, the highly stereoselectivity attending C-C bond formation, and its applicability to C-glycosylations using both armed and disarmed pentose and hexose derivatives.

NEW HYDROXYACID DERIVATIVES, A PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

Compounds of formula (I): wherein R1, R2, R3, R4, R5, R6, R7, R8, R14, A and n are as defined in the description. Medicaments.

Chemoenzymatic synthesis of neoglycoproteins driven by the assessment of protein surface reactivity

In this paper a series of 2-iminomethoxyethyl mannose-based mono- and disaccharides have been synthesized by a chemoenzymatic approach and used in coupling reactions with ε-amino groups of lysine residues in a model protein (ribonuclease A, RNase A) to give semisynthetic neoglycoconjugates. In order to study the influence of structure of the glycans on the conjugation outcomes, an accurate characterization of the prepared neoglycoproteins was performed by a combination of ESI-MS and LC-MS analytical methods. The analyses of the chymotryptic digests of the all neoglycoconjugates revealed six Lys-glycosylation sites with a the following order of lysine reactivity: Lys 1 Lys 91 ? Lys 31 > Lys 61 ? Lys 66. A computational analysis of the reactivity of each lysine residue has been also carried out considering several parameters (amino acids surface exposure and pKa, protein flexibility). The in silico evaluation seems to confirm the order in lysine reactivity resulting from proteomic analysis.

Synthesis of multi-galactose-conjugated 2′-O-methyl oligoribonucleotides and their in vivo imaging with positron emission tomography

68Ga labelled 2′-O-methyl oligoribonucleotides (anti-miR-15b) bearing one, three or seven d-galactopyranoside residues have been prepared and their distribution in healthy rats has been studied by positron emission tomography (PET). To obtain t

In(III) triflate-catalyzed detritylation and glycosylation by solvent-free ball milling

A highly efficient In(III) triflate-assisted method for the detritylation of O-trityl derivatives of carbohydrates, phenols, and alcohols using solvent-free mechanochemical method is described. In the case of carbohydrates, further reaction in the presence of an acceptor sugar leads to highly efficient glycosylation in the same pot resulting in the formation of the desired glycoside-product in very high yields. The method was applied successfully to the synthesis of a combinatorial library of galactose-based (1,6)-linked cyclohexa-, hepta-, and octasaccharides on gram scale.

Lipases in the regioselective preparation of glyceric acid esters of methyl glycosides

The lipase-catalyzed regioselective acylation of methyl α-D-galacto-, -gluco- and -mannopyranosides with isopropylidene-protected (R)- and (S)-glyceric acid methyl esters in organic solvents is presented. Factors affecting the formation of the 6-O-mono- and 2,6-O-diacylated products are examined and preparative-scale reactions are detailed. In addition, studies on partially protected methyl α-D-galactopyranosides are presented, with the 3,4-O-isopropylidene protected compound leading exclusively to the formation of the 6-O-monoacylated product even at high substrate concentrations. Application of acidic resin in methanol allows removal of the isopropylidene protection groups without disturbing the ester bond at C-6. Copyright