72033-44-4

Usage

Chemical compound

A substance formed by a chemical reaction, with a specific molecular structure and properties.

Complex molecular structure

The compound has a multi-part structure, consisting of various functional groups and moieties.

Indolyl group

A heterocyclic aromatic ring system derived from indole, which is a part of the compound's structure.

Amino group

A functional group containing a nitrogen atom bonded to two hydrogen atoms (-NH2), present in the compound.

Oxoethyl group

A functional group containing a carbonyl group (C=O) attached to an ethyl group (-CH2CH3), which is part of the compound.

Hexopyranuronic acid moiety

A six-carbon sugar derivative with a carboxylic acid group, which is a component of the compound.

Methyl ester functional group

An ester formed by the reaction of a carboxylic acid and methanol, which is part of the compound's structure.

Synthetic derivative

The compound is not found naturally but is created through chemical synthesis.

Potential applications

The compound may have uses in the pharmaceutical or research fields, although specific applications are not readily available.

Biological activity

The compound's complex structure suggests it may interact with biological systems, making it a potential target for further study.

Further study

The compound's properties and potential applications may warrant additional research to better understand its interactions with biological systems and possible uses.

Upstream product

• 186581-53-3 diazomethane 
• 771-51-7 indole-3-acetonitrile 
• 125287-91-4 methyl 1-chloro-1,4-dideoxy-2,3-di-O-pivaloyl-α-D-lyxo-hexopyranuronate 
• 129530-46-7 1-O-methyl-2,3-O-isopropylidene-α-D-mannuronic acid methyl ester 
• 1346418-10-7 methyl 2,3-O-isopropylidene-4-O-imidazolylthiocarbonyl-α-D-mannopyranosiduronic acid methyl ester 
• 1346418-12-9 methyl 2,3,4-tri-O-pivaloyl-α-D-mannopyranosiduronic acid methyl ester 
• 1346418-11-8 C₁₈H₂₈O₈ 
• 1346418-13-0 1-bromo-1,4-dideoxy-2,3-di-O-pivaloyl-α-D-lyxohexopyranosyluronic acid methyl ester 
• 1346418-14-1 (2S,6S)-6-(tert-butyldimethylsilyloxymethyl)-2-isopropoxy-2,5-dihydropyran 
• 1346418-15-2 isopropyl 6-O-(tert-butyldimethylsilyl)-4-deoxy-α-D-lyxohexopyranoside 
• 1346418-16-3 isopropyl 6-O-(tert-butyldimethylsilyl)-4-deoxy-2,3-di-O-pivaloyl-α-D-lyxohexopyranoside 
• 1346418-17-4 isopropyl 4-deoxy-2,3-di-O-pivaloyl-α-D-lyxohexopyranoside 
• 1346418-18-5 isopropyl 4-deoxy-2,3-di-O-pivaloyl-α-D-lyxohexopyranosiduronic acid methyl ester 
• 1346418-20-9 C₁₁H₁₈O₄ 

Relevant academic research and scientific papers

Synthesis of the Indole Nucleoside Antibiotics Neosidomycin and SF-2140: Structural Revision of Neosidomycin

Two structurally related indole nucleoside antibiotics, neosidomycin (5) and SF-2140 (3) have been synthesised; it is confirmed that the structure initially proposed for neosidomycin must be revised.

Enantioselective de novo synthesis of 4-deoxy-d-hexopyranoses via hetero-Diels-Alder cycloadditions: Total synthesis of ezoaminuroic acid and neosidomycin

The de novo synthesis of carbohydrates constitutes an important aspect of organic chemistry, and its application toward deoxy sugars is particularly noteworthy in targeting biologically active compounds. The enantioselective preparation of 4-deoxy-d-ribo-, 4-deoxy-d-lyxo-, and 4-deoxy-d-xylo- hexopyranosides, along with their uronate counterparts has been successfully accomplished using hetero-Diels - Alder reactions as the key step. Jacobsen chromium(III) catalyst and a titanium - binaphthol complex have been used to successfully catalyze diene and aldehyde cycloadditions, leading to optically active dihydropyran templates. 6-Hydroxydesosamine, orthogonally protected ezoaminuroic acid, and neosidomycin were synthesized using a comparative study. Also, a novel chiron approach to 4-deoxy-lyxo-hexopyranosiduronic acid methyl ester derivatives was efficiently accomplished starting from readily accessible starting materials. This work represents a systematic and comprehensive study toward a de novo synthesis of 4-deoxy-hexopyranoses via enantioselective hetero-Diels-Alder reactions.

Synthesis of the Indole Nucleoside Antibiotics Neosidomycin and SF-2140

The indole nucleoside antibiotics neosidomycin 5 and SF-2140 3 have been synthesized.Methyl 4-deoxy-2,3-O-isopropylidene-α-D-lyxo-hexopyranoside 8 was converted into methyl 1-chloro-1,4-dideoxy-2,3-di-O-pivaloyl-α-D-lyxo-hexopyranuronate 33 in five steps.Silver(I)-catalysed coupling of compound 33 with 3-(cyanomethyl)indole 20 gave stereoselectively an α-nucleoside which was converted into methyl 1--1,4-dideoxy-α-D-lyxo-hexopyranuronate (neosidomycin, 5).Coupling of compound 33 to 3-cyanomethyl-4-methoxyindole 23 by the sodium salt procedure, and subsequent deacylation, gave methyl 1-(3-cyanomethyl-4-methoxyindol-1-yl)-1,4-dideoxy-α-D-lyxo-hexopyranuronate (SF-2140, 3).Neosidomycin, SF-2140, and their O-acyl derivatives adopt a conformation which differs from that of 1-(6-O-benzoyl-4-deoxy-2,3-O-pivaloyl-α-D-lyxo-hexopyranosyl)-3-(cyanomethyl)indole 29, in which the methyl uronate grouping of the antibiotics is present at a lower oxidation level.