[2S,3S,(-)]-2,3-Dihydroxy-2-isopropylbutanoic acid

Base Information

• Chemical Name: [2S,3S,(-)]-2,3-Dihydroxy-2-isopropylbutanoic acid
• CAS No.: 17132-48-8
• Molecular Formula: C7H14 O4
• Molecular Weight: 162.1837
• Hs Code.: 2918290000
• Mol file: 17132-48-8.mol

Synonyms:Butanoicacid, 2,3-dihydroxy-2-(1-methylethyl)-, [S-(R*,R*)]-; Butyric acid,2,3-dihydroxy-2-isopropyl-, (2S,3S)- (8CI); (-)-(2'S,3'S)-Viridifloric acid;(-)-Viridifloric acid; (-)-Viridiflorinoic acid; (2S,3S)-Viridifloric acid

Chemical Property of [2S,3S,(-)]-2,3-Dihydroxy-2-isopropylbutanoic acid

Chemical Property:

• Vapor Pressure: 1.11E-05mmHg at 25°C
• Boiling Point: 331.7°Cat760mmHg
• Flash Point: 168.6°C
• PSA: 77.76000
• Density: 1.205g/cm³
• LogP: -0.16110

Purity/Quality:

(2S,3S)-ViridifloricAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (2S,3S)-Viridifloric Acid is an intermediate in the synthesis of (+)-Lycopsamine (L487525), which occurs in pyrrolizidine alkaloid-containing plants, which are the most common poisonous plants affecting livestock, wildlife, and humans. They are being known as hepatotoxins and tumorigens.It has been shown that pyrrolizidine Alkaloid-Derived DNA Adducts, are the common biological biomarker of pyrrolizidine alkaloid-induced liver tumor formation.

Technology Process of [2S,3S,(-)]-2,3-Dihydroxy-2-isopropylbutanoic acid

There total 24 articles about [2S,3S,(-)]-2,3-Dihydroxy-2-isopropylbutanoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

ethyl (2S,3S)-2,3-dihydroxy-2-(1-methylethyl)butyrate → (2S,3S)-2,3-dihydroxy-2-(1-methylethyl)butyric acid (17132-48-8)

Guidance literature:

With barium hydroxide octahydrate; water; at 50 ℃; for 4h;

DOI:10.1021/ol300466a

Reference yield: 80.0%

(+)-Echinatine (480-83-1,26131-12-4) → (2S,3S)-2,3-dihydroxy-2-(1-methylethyl)butyric acid (17132-48-8) + (+)-heliotridine (520-63-8)

Guidance literature:

With barium dihydroxide;

Reference yield:

ethyl 2-(1-methylethyl)but-2-enoate (856183-33-0) → (2S,3S)-2,3-dihydroxy-2-(1-methylethyl)butyric acid (17132-48-8) + (2S,3R)-2,3-dihydroxy-2-(1-methylethyl)butyric acid (23944-48-1) + (2R,3S)-2,3-dihydroxy-2-(1-methylethyl)butyric acid (23944-50-5) + (+)-viridifloric acid (17233-93-1)

Guidance literature:

ethyl 2-(1-methylethyl)but-2-enoate; With AD-mix-α; methanesulfonamide; In water; tert-butyl alcohol; at 0 ℃; for 42h;

With potassium hydroxide; In ethanol; water; at 50 ℃; for 36h; Further stages. Title compound not separated from byproducts.;

DOI:10.1002/1099-0690(200211)2002:22<3884::AID-EJOC3884>3.0.CO;2-4

upstream raw materials:

(+/-)-trachelanthic acid

(E)-2-(1-methylethyl)-2-butenoic acid

ethanol

parsonine

Downstream raw materials:

4-methyl-2,3-pentanedione

Amabiline

O,O'-Dibenzyl-(-)-viridiflorinsaeure-methylester

lycopsamine N-oxide

Refernces

• 1、 Senter, Timothy J.,Fadeyi, Olugbeminiyi O.,Lindsley, Craig W.. "Enantioselective total synthesis of (+)-amabiline". . p. 1869 - 1871. Retrieved 2012/05/20.
• 2、 Kunec, Ellen K.,Robins, David J.. "Pyrrolizidine Alkaloid Biosynthesis. Synthesis of 3H-Labelled Trachelanthamidine and Isoretronecanol and their Incorporation into Three Pyrrolizidine Bases (Necines)". . p. 1437 - 1441. Retrieved 2007/10/02.