136737-07-0

Usage

Uses

Used in Organic Synthesis:
Methyl4,5,7,8,9-penta-O-acetyl-2,6-anhydro-3-deoxy-D-glycero-D-galacto-non-2-enonate is used as a synthetic intermediate for the production of various organic compounds. Its application in this field is due to its unique chemical structure, which allows for further functionalization and the formation of a wide range of derivatives.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Methyl4,5,7,8,9-penta-O-acetyl-2,6-anhydro-3-deoxy-D-glycero-D-galacto-non-2-enonate is used as a key building block for the development of novel drug candidates. Its versatile chemical properties enable the synthesis of bioactive molecules with potential therapeutic applications.
Used in Chemical Research:
Methyl4,5,7,8,9-penta-O-acetyl-2,6-anhydro-3-deoxy-D-glycero-D-galacto-non-2-enonate is also employed in chemical research as a model compound for studying various reaction mechanisms and exploring new synthetic methodologies. Its unique structure provides valuable insights into the reactivity of similar compounds and helps in the development of innovative synthetic strategies.

Upstream product

• 123843-50-5 methyl (2,4,5,7,8,9-hexa-O-acetyl-3-deoxy-D-glycero-β-D-galacto-2-nonulopyranosid)onate 
• 108-24-7 acetic anhydride 
• 120123-43-5 3-deoxy-D-glycero-β-D-galacto-non-2-ulopyranosonic acid methyl ester 
• 139110-77-3 methyl 4,5,7,8,9-penta-O-acetyl-2,6-anhydro-2-chloro-2,3-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate 
• 53685-11-3 methyl 2,6-di-O-benzyl-β-D-galactopyranoside 
• 1227468-34-9 methyl (1-adamantanyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranosid)onate 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 40653-32-5 methyl 2,3,4-tri-O-benzyl-β-D-galactopyranoside 
• 1227468-35-0 methyl (1-adamantanyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranosid)onate 
• 107020-85-9 (4S,5R,6R)-4-Acetoxy-5-acetylamino-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 118977-25-6 methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-galacto-2-nonulopyranoside)onate 
• 65072-58-4 sodium 3,5-dimethylbenzene thiolate 
• 930-69-8 sodium thiophenolate 
• 18803-44-6 sodium p-chlorothiophenolate 

Downstream Products

• 263155-12-0 4-amino-2,6-anhydro-3,4-dideoxy-D-glycero-D-galacto-non-2-enonic acid 
• 263155-12-0 4-amino-2,6-anhydro-3,4-dideoxy-D-glycero-D-talo-non-2-enonic acid 
• 402561-96-0 methyl 2,6-anhydro-3-deoxy-9-O-p-toluenesulfonyl-D-glycero-D-galacto-non-2-enoate 
• 173467-19-1 methyl 5,7,8,9-tetra-O-acetyl-4-acetylamino-2,6-anhydro-3,4-dideoxy-D-glycero-D-talo-non-2-enonate 
• 173467-18-0 methyl 5,7,8,9-tetra-O-acetyl-4-acetylamino-2,6-anhydro-3,4-dideoxy-D-glycero-D-galacto-non-2-enonate 
• 188854-96-8 2,6-anhydro-3-deoxy-D-glycero-D-galacto-non-2-enonic acid 

Relevant academic research and scientific papers

Syntheses of 2,6-anhydro-3-deoxy-D-glycero-D-galacto-non-2-enonic acid (KDN2en) and its hydrogenation products

Methyl 4,5,7,8,9-penta-O-acetyl-2,6-anhydro-3-deoxy-D-glycero-D-galacto-non-2-enonate (5) was synthesized from KDN methyl ester 2 with a catalytic amount of concentrated sulfuric acid in acetic anhydride, or from 2-chloro-KDN methyl ester 4 with DBU in good yield. Hydrogenation of 4 and 5 with 10% Pd-C gave 2-deoxy-2-Hax-KDN 8 and 2-deoxy-2-Heq-KDN derivative 11 in high yield, respectively. The structures of these compounds were elucidated from the MS, elemental analysis, 1H NMR and 13C NMR data.

Synthesis of 4-oxo and 4-hydroxyimino-4-deoxy-Kdn2en derivatives

2,6-Anhydro-3-deoxy-D-manno-non-2-en-4-ulosonic acid (4-oxo-Kdn2en, 2) was synthesized from methyl 2,6-anhydro-3-deoxy-D-glycero-D-galacto-non-2-enonate (Kdn-2en methyl ester, 7) by the oxidation with manganese dioxide in dry acetone in good yield. 4-Hydroxyimino-Kdn2en derivatives (3), and 4-carbethoxymethylene-Kdn2en derivatives (4) were synthesized from the peracetylated methyl ester of 4-oxo-Kdn2en by oximation and Wittig reaction in good yield, respectively.

2,3-Didehydro-2-deoxysialic acids structurally varied at C-5 and their behaviour towards the sialidase from Vibrio cholerae

2,3-Didehydro-2-deoxy-N-trifluoroacetylneuraminic acid (5-trifluoroacetyl-Neu2en) (3) has been synthesised from Neu5Ac2en (1) by hydrazinolysis, to give Neu2en (2), followed by N-trifluoroacetylation. 2,3-Didehydro-2,3-dideoxy-D-glycero-D-galacto-2-nonulopyranosonic acid (Kdn2en, 8) and 5-azido-2,3-didehydro-2,3,5-trideoxy-D-glycero-D-galacto-2-nonulopyranosonic acid (5-azido-5-deoxy-Kdn2en, 9) have been prepared from the acetylated methyl esters of Kdn (4) and 5-azido-5-deoxy-Kdn (5) via Zemplen saponification.The behaviour of the above 2,3-didehydro-2-deoxysialic acids towards Vibrio cholerae sialidase has been investigated.

Facile anomer-oriented syntheses of 4-methylumbelliferyl sialic acid glycosides

As part of a program to find new sialidases and determine their enzymatic specificity and catalytic activity, a library of 4-methylumbelliferyl sialic acid glycosides derivatised at the C-5 position were prepared fromN-acetylneuraminic acid. Both α- and β-4-methylumbelliferyl sialic acid glycosides were prepared in high yields and stereoselectivity. α-Anomers were accessedviareagent control by utilising additive CH3CN and TBAI, whereas the β-anomers were synthesised through a diastereoselective addition reaction of iodine and the aglycone to the corresponding glycal followed by reduction of the resulting 3-iodo compounds. Both anomer-oriented synthetic pathways allow for gram-scale stereoselective syntheses of the desired C-5 modified neuraminic acid derivatives for use as tools to quantify the enzymatic activity and substrate specificity of known sialidases, and potential detection and investigation of novel sialidases.

Structurally homologous sialidases exhibit a commonality in reactivity: Glycoside hydrolase-catalyzed hydrolysis of Kdn-thioglycosides

Aspergillus fumigatus is one of the main causative agents of invasive aspergillosis, an often-lethal fungal disease that affects immunocompromised individuals. A. fumigatus produces a sialidase that cleaves the nine-carbon carbohydrate Kdn from glycoconju

Stereoselective synthesis of α-Keto-deoxy-D-glycero-D- galactononulosonic acid glycosides by means of the 4,5-O-carbonate protecting group

(Figure Presented) Unrivaled: A 1-adamantyl thioglycoside derivative of the nonulosonic acid KDN, carrying a 4,5-O-carbonate protecting group, is a highly efficient and a-selective KDN donor when activated using N-iodosuccinimide (NIS) and trifluoromethanesulfonic acid (TfOH). Glycosylates conducted with this protecting group do not suffer from competing glycal formation.

Novel practical synthesis of Kdn2en and its C-4 nitrogen-modified derivatives

A practical synthesis of Kdn2en and 4-amino-4-deoxy-Kdn2en has been achieved via a key intermediate, methyl 4,5,7,8,9-penta-O-acetyl-2,6-anhydro- 3-deoxy-D-glycero-D-galacto-non-2-enonate, which has been prepared from Kdn in three steps in 91% overall yield. (C) 2000 Elsevier Science Ltd.

A novel glycosylation of 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) via in situ pyranose-furanose rearrangement

In studies on the glycosylation of 3-deoxy-D-glycero-D-galacto-2- nonulosonic acid (KDN) derivatives, O-glycosides of furanose-type KDN were synthesized from benzyl 4,5,7,8,9-penta-O-acetyl-2-bromo-2,3-dideoxy-D- glycero-D-galacto-2-nonulopyranosonate under Koenigs-Knorr reaction conditions. The furanoid structures of the KDN moiety were supported by with 1H-NMR experiments, and the reaction was considered as a novel glycosylation with ring contraction, which proceeded via in situ pyranose-furanose rearrangement of the KDN moiety, and subsequent coupling with acceptors.