180992-28-3

Basic information

• Product Name: 2(S),3(S),5-Trihydroxy-4(R)-[11(R)-hydroxy-2,4(R),6,8,10(S),12(S)-hexamethyl-5-oxodocosa-2(E),6(E),8(E)-trienoyloxy]pentanoic acid
• Synonyms: Khafrefungin
• CAS NO: 180992-28-3
• Molecular Formula: C₃₃H₅₆O₉
• Molecular Weight: 596.80887
• Mol File: 180992-28-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2(S),3(S),5-Trihydroxy-4(R)-[11(R)-hydroxy-2,4(R),6,8,10(S),12(S)-hexamethyl-5-oxodocosa-2(E),6(E),8(E)-trienoyloxy]pentanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2(S),3(S),5-Trihydroxy-4(R)-[11(R)-hydroxy-2,4(R),6,8,10(S),12(S)-hexamethyl-5-oxodocosa-2(E),6(E),8(E)-trienoyloxy]pentanoic acid(180992-28-3)
• EPA Substance Registry System: 2(S),3(S),5-Trihydroxy-4(R)-[11(R)-hydroxy-2,4(R),6,8,10(S),12(S)-hexamethyl-5-oxodocosa-2(E),6(E),8(E)-trienoyloxy]pentanoic acid(180992-28-3)

Safety Data

• Hazardous Substances Data: 180992-28-3(Hazardous Substances Data)

Usage

Molecular structure

2(S),3(S),5-Trihydroxy-4(R)-[11(R)-hydroxy-2,4(R),6,8,10(S),12(S)-hexamethyl-5-oxodocosa-2(E),6(E),8(E)-trienoyloxy]pentanoic acid is a complex organic compound with a long-chain structure and multiple functional groups.

Functional groups

This compound contains three hydroxyl (-OH) groups attached to the second, third, and fifth carbon atoms, indicating the presence of alcohol-like properties.

Chiral carbon

The 4(R) configuration indicates that the fourth carbon atom is chiral, meaning that it has four different substituents attached to it, which can lead to different spatial arrangements of the molecule.

Fatty acid derivative

The hexamethyl-5-oxodocosa-2(E),6(E),8(E)-trienoyloxy group attached to the 11th carbon suggests that this compound is derived from a long-chain fatty acid, which can be important for biological functions.

Biological activity

The compound's structure suggests that it may have biological activity, potentially playing a role in various biochemical processes within living organisms.

Upstream product

• 361525-10-2 (2S,3S,4R)-2,3,5-tris(4-methoxybenzyloxy)-4-[[(2E,4R,6E,8E,10S,11R,12S)-1,5-dioxo-2,4,6,8,10,12-hexamethyl-11-(4-methoxybenzyloxy)-2,6,8-docosatrienyl]oxy]pentanoic acid 
• 932406-88-7 11-(tert-butyl-dimethyl-silanyloxy)-2,4,6,8,10,12-hexamethyl-5-oxo-docosa-2,6,8-trienoic acid 3-carboxy-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-propyl ester 
• 773896-71-2 2-allyloxy-5-hydroxymethyl-tetrahydro-furan-3,4-diol 
• 932406-79-6 7-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-hept-5-en-3-one 
• 932406-84-3 7-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-hept-5-en-3-ol 
• 932406-83-2 3-(5-hydroxy-2,4-dimethyl-hept-2-enoyl)-4-isopropyl-oxazolidin-2-one 
• 932406-78-5 5-(tert-butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-hexadec-2-enal 
• 932406-81-0 3-(5-hydroxy-2,4,6-trimethyl-hexadec-2-enoyl)-4-isopropyl-oxazolidin-2-one 
• 932406-82-1 3-[5-(tert-butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-hexadec-2-enoyl]-4-isopropyl-oxazolidin-2-one 
• 932406-77-4 5-(tert-butyl-dimethyl-silanyloxy)-1,3,4-tris-(4-methoxy-benzyloxy)-pentan-2-ol 
• 932406-91-2 11-(tert-butyl-dimethyl-silanyloxy)-2,4,6,8,10,12-hexamethyl-5-oxo-docosa-2,6,8-trienal 
• 932406-90-1 11-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-2,4,6,8,10,12-hexamethyl-docosa-2,6,8-trien-5-one 
• 932406-76-3 11-(tert-butyl-dimethyl-silanyloxy)-2,4,6,8,10,12-hexamethyl-5-oxo-docosa-2,6,8-trienoic acid 
• 932406-86-5 1,11-bis-(tert-butyl-dimethyl-silanyloxy)-2,4,6,8,10,12-hexamethyl-docosa-2,6,8-trien-5-one 

Relevant articles and documents

Total synthesis of khafrefungin using highly stereoselective vinylogous Mukaiyama aldol reaction

(Chemical Equation Presented) A convergent total synthesis of khafrefungin was accomplished on the basis of (1) the highly stereoselective TiCl 4-mediated vinylogous Mukaiyama aldol reaction using vinylketene silyl N,O-acetal and (2) syn-select

Efficient total synthesis of khafrefungin: Convergent approach using Suzuki coupling under thallium-free conditions toward multigram-scale synthesis

An efficient and practical synthetic route to khafrefungin, an antifungal agent, has been developed based on successive coupling of three components, 3, 4, and then 2. A key step of the synthesis is the Suzuki coupling of 2 and 10, in which the use of tox

Convergent total synthesis of khafrefungin and its inhibitory activity of fungal sphingolipid syntheses

A convergent total synthesis of khafrefungin, a novel inhibitor of fungal sphingolipid syntheses isolated from the fermentation culture MF6020, has been developed. Alkenylboronic acid 5 and alkenyliodide 6, key fragments for the total synthesis, were prepared from the corresponding achiral aldehydes using tin(II)-catalyzed and Zr(IV)-catalyzed asymmetric aldol reactions, respectively. The Suzuki coupling reaction of these two fragments was successfully performed to give 17 in good yield. Through the total synthesis, epimerization of the C4 position having a rather highly acidic proton did not occur, indicating that khafrefungin was under strict conformational constraints to prevent the epimerization process. This characteristic stability of khafrefungin has also been discussed using semiempirical calculation and synthesis. Finally, khafrefungin derivatives have also been synthesized, and their antifungal activities have been measured to obtain information on the structure-activity relationships.