85549-51-5

Usage

Uses

Used in Organic Synthesis:
METHYL (METHYL 3-DEOXY-D-ARABINO-HEPTULOPYRANOSID)URONATE is used as a key intermediate in the synthesis of complex organic molecules. Its unique structure allows for the formation of various chemical bonds and reactions, making it a valuable component in the creation of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, METHYL (METHYL 3-DEOXY-D-ARABINO-HEPTULOPYRANOSID)URONATE is used as a building block for the development of novel drug candidates. Its ability to participate in various chemical reactions enables the synthesis of new compounds with potential therapeutic properties, contributing to the discovery of innovative treatments for various diseases.
Used in Agrochemical Industry:
METHYL (METHYL 3-DEOXY-D-ARABINO-HEPTULOPYRANOSID)URONATE also finds application in the agrochemical industry, where it is utilized in the synthesis of new pesticides, herbicides, and other crop protection agents. Its versatility in organic synthesis allows for the development of more effective and environmentally friendly products to enhance crop yields and protect against pests.
Used in Specialty Chemicals:
In the specialty chemicals sector, METHYL (METHYL 3-DEOXY-D-ARABINO-HEPTULOPYRANOSID)URONATE is employed as a crucial component in the production of various high-value chemicals. Its unique properties make it suitable for use in the synthesis of compounds used in materials science, coatings, adhesives, and other industrial applications.

Upstream product

• 67-56-1 methanol 
• 56742-43-9 3-deoxy-2-keto-D-arabino-heptonic acid 
• 194155-44-7 (2S,4R,5R,6R)-4,5-Diacetoxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 194155-43-6 (2S,4S,5S,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-4,5-dihydroxy-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 194155-40-3 (2S,4S,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 194155-42-5 (2S,4S,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 194155-45-8 (2S,4R,5R,6R)-4,5-Diacetoxy-6-acetoxymethyl-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 211934-98-4 2,6-anhydro-4,5,7-tri-O-benzyl-1-(propane-1,3-diyl-dithioacetal)-1,3-dideoxy-D-lyxo-hept-1-enitol 
• 72605-77-7 (2R,3R,4R)-3,4-bis-benzyloxy-2-benzyloxymethyltetrahydropyran-5-one 
• 221450-00-6 2,6-anyhdro-4,5,7-tri-O-(tert-butyldimethylsilyl)-1-(propane-1,3-diyl-dithioacetal)-1,3-dideoxy-D-lyxo-hept-1-enitol 
• 221450-08-4 methyl onate 
• 211935-00-1 methyl (methyl 4,5,7-tri-O-benzyl-3-deoxy-α-D-lyxo-hept-2-ulopyranosid)onate 
• 29873-81-2 3-Desoxy-D-lyxo-heptulosansaeure 
• 165875-82-1 methyl onate 

Downstream Products

• 194155-46-9 (2S,4R,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 194155-56-1 (2S,4S,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 90318-59-5 methyl (methyl 3-deoxy-α-D-arabino-hept-2-ulopyranosid)onate 7-(dihydrogen phosphate) 
• 194155-55-0 (2R,4S,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Synthetic routes to methyl 3-deoxy-aldulosonic acid methyl esters and their 2-deoxy isomers based on the Horner-Emmons and Peterson reaction of sugar lactones

The two reagents: 2-trimethylsilyl- and 2-[bis(2,2,2- trifluoroethoxy)phosphoryl]-1,3-dithianes were engaged in the construction of appropriate ketene thioacetals from the isomeric 2-deoxy-hexono-1,5-lactones via Horner-Emmons or Peterson reaction. A comparison of the results shows that the second reagent is more promising, as it forms the desired ketene thioacetals as sole products. The latter were directly transformed stereoselectively into the title α ulosonates in an oxidative hydrolysis reaction, using NBS/MeOH in CH2Cl2. A construction of the methyl 2-deoxy- ulosonates involved a preceding hydrogenation of the double bond by LiBH4- TMSCl species, and subsequent hydrolysis with NBS in aqueous THF medium.

Synthesis of higher 3-deoxy-2-ketoaldonic acids by construction and deoximation of their hydroxyiminoesters

The synthesis of natural 3-deoxy-2-keto-D-arabino-heptonic and 3-deoxy-2-keto-D-manno-octonic acids is reported, involving preparation of polyalkyl malonates and higher hydroxyiminoester derivatives of the target acids, followed by deoximation of the latter with nitrosylsulfuric acid, hydrolysis of the protective groups, and identification of the acids as their methyl ester methyl glycoside or ammonium salt. A mixture of products of acidic C-nitrosation of 2-hydroxycarbonyl-2,3-dideoxy-5,6:7,8-di-O-isopropylidene-D-manno-octono-1,4-lac tone was characterized in a similar way. Three procedures for deoximation of the key oximes with nitrosylsulfuric acid in ether, as well as in acetic and formic acids were proposed.

The first synthesis of the ketene dithioacetals from sugar lactones: A convenient access to 3-ulosonic acids

Isomeric 2-deoxy aldonolactones undergo Horner-Emmons reactions with 2- [bis(2,2,2-trifluoroethoxy)phosphoryl]1,3-dithiane, to give the corresponding ketene dithioacetals, which are the key intermediates in the synthesis of 3- deoxy-2-keto-aldonic acids.

Convenient preparation of α- and β-glycosides of novel isomeric 3-deoxy-hept-2-ulosaric acids diesters

Methyl 3-deoxy-α and β-D-ribo, D-xylo and D-lyxo-hept-2-ulosonic acids were obtained from the individual α and β anomers of the same methyl (methyl 3-deoxy-D-arabino-hept-2-ulopyranosid)onate in a sequential epimerisation at C-4 and/or C-5 of their appropriate O-trifluoromethanesulfonic derivatives, using cesium acetate. Subsequent oxidation of the 7-OH group in these compounds lead to the new isomeric 3-deoxy-hept-2-ulosaric acids derivatives.

A novel chemical synthesis of a 3-deoxy-D-arabino-heptulosonic acid 7-phosphate (DAHP) derivative and its 2-deoxy analogue

Using 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl cyanide as a precursor, methyl (methyl 3-deoxy-α-D-arabino-hept-2-ulopyranosid)onate (6) and its 2-deoxy analogue (10) were prepared. The synthesis involved an elimination of one molecule of acetic acid from C-2-C-3 and transformation of the CN group into COOMe, followed by methoxymercuration with subsequent reductive removal of the mercuri residue to give 6 or hydrogenation of the double bond to give 10. Phosphorylation of the 7-OH group led to the title compounds.

Synthesis of sialyl Lewis X mimetics and related structures using the glycosyl phosphite methodology and evaluation of E-selectin inhibition

This paper describes our recent study of glycosyl phosphites for glycosylation reactions, with particular emphasis on the investigation of protecting group and stereochemistry effects on the anomeric reactivity and stereoselectivity, and the application of this methodology to the synthesis of Lewis X (Le(x)), Lewis Y (Le(y)), glycopeptides, and sialyl Lewis X (SLe(x)) mimetics. Both α-O-fucosyl-L-threonine and α-O-fucosyl-(1R,2R)-2-aminocyclohexanol were found to be effective templates for the chemical/enzymatic synthesis of SLe(x) mimetics, and some fucopeptides prepared were 5-10 times more active than SLe(x) as inhibitors of E-selectin.

The first synthesis of 3-deoxy-D-lyxo-2-heptulosaric acid (DHA) derivatives

Synthetic route to the methyl ester of methyl glycoside of 3-deoxy-D-lyxco-heptulosaric acid (13) starting from 1-cyanogalactal 2 is described. The latter substance was prepared by direct elimination of acetic acid from 1 using 1,8-diazabicyclo[5.4.0]unde

Synthesis of 4-amino-3,4-dideoxy-D-arabino-heptulosonic acid 7-phosphate, the biosynthetic precursor of C7N units in ansamycin antibiotics

The synthesis of 4-amino-3,4-dideoxy-D-arabino-heptulosonic acid 7-phosphate (15), the first committed intermediate in a new branch of the shikimate pathway of aromatic biosynthesis, is reported from 2-deoxy-D-glucose in 14 steps in 10-12percent overall y

Determination of the Anomeric Configuration in Glycosides of 3-Deoxy-2-aldulosonic Acids by Circular Dichroism and X-Ray Crystallography

Methyl (methyl 3-deoxy-D-arabino-2-heptulopyranosid)onate was obtained by acid-catalysed esterification and glycosidation of the free 2-aldulosonic acid.The molecular geometry of the glycosidic ester was determined by X-ray crystallography, and indicated both that the molecule was α-anomer and that the ring oxygen and the carboxy-group were nearly coplanar.The c.d. spectrum showed a negative n -> ?* transition band centred at 224 nm.The c.d. spectra od a number of methyl glycopyranosides derived from 6-, 7-, and 8-carbon 3-deoxy-2-aldulosonic acids demonstrated that all the compounds believed to be α-glycosides had negative maxima, and all those believed to be β-glycosides had positive maxima around 220 nm independent of their 2C5 or5C2 conformation.The only known furanoside, believed to be a β-anomer, also had a positive maximum.The chirality of the anomeric carbon atom of this class of compound can thus be conveniently established by determining the sign of the Cotton effect at 220 nm.