42890-76-6

Basic information

• Product Name: (S)-1,2,4-Butanetriol
• Synonyms: (S)-Butane-1,2,4-triol;(S)-1,2,4-Butanetriol,95%,99% ee;(2S)-(-)-1,2,4-Trihydroxybutane;ASTM D6584 1,2,4-Butanetriol Solution ;(S)-(-)-1,2,4-BUTANETRIOL;(S)-1,2,4-BUTANETRIOL;(S)-(-)-1,2,4-TRIHYDROXYBUTANE;(2S)-BUTANE-1,2,4-TRIOL
• CAS NO: 42890-76-6
• Molecular Formula: C₄H₁₀O₃
• Molecular Weight: 106.12
• EINECS: -0
• Product Categories: Chiral Building Blocks;Simple Alcohols (Chiral);Synthetic Organic Chemistry;Chiral Building Blocks;Organic Building Blocks;Polyols
• Mol File: 42890-76-6.mol
• Article Data: 89

Chemical Properties

• Boiling Point: 150 °C0.04 mm Hg(lit.)
• Flash Point: >110°C
• Appearance: /
• Density: 1.19 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.475(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Sparingly), Water (Slightly)
• PKA: 14.02±0.20(Predicted)
• Water Solubility: soluble
• Sensitive: Hygroscopic
• BRN: 1719408
• CAS DataBase Reference: (S)-1,2,4-Butanetriol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1,2,4-Butanetriol(42890-76-6)
• EPA Substance Registry System: (S)-1,2,4-Butanetriol(42890-76-6)

Safety Data

• Hazard Codes: F,Xn
• Statements: 36/37/38-41-20/21/22-11
• Safety Statements: 23-24/25-39-26-16-36/37-28-33-29-9
• RIDADR: UN 3316 9/PG 2
• WGK Germany: 3
• F: 3-10-21
• Hazardous Substances Data: 42890-76-6(Hazardous Substances Data)

Usage

Description

(S)-(-)-1,2,4-Butanetriol can be prepared via reduction of (S)-malic acid in the presence of borane-dimethyl sulfide. (S)-(-)-1,2,4-Butanetriol may be used as a starting material in the enantioselective total syntheses of (+)-azimine and (+)-carpaine.?It can also be used to prepare the organic building blocks?(+)-3,4-epoxy-1-butanol,?(2S,4S)-4-(hydroxymethyl)-2-ferrocenyl-1,3-dioxan,?(S)-1,2,4-triacetoxybutane via acetylation with acetic anhydride,?and (S)-1,2,4-tris-(3,5-dinitrobenzoy1oxy)butane via esterification with 3,5-dinitrobenzoyl chloride, and so on.

Chemical Properties

clear colorless viscous liquid

Uses

Glycerophospholipids act as regulators of various enzyme activities, and can be used as biological markers to indicate pathological states.

Upstream product

• 97-67-6 (S)-Malic acid 
• 691-84-9 Diethyl (S)-malate 
• 636-61-3 D-Malic acid 
• 51067-83-5 1,1-diphenyl-silolan-3-ol 
• 627-27-0 homoalylic alcohol 
• 5055-09-4 (2S,2'RS) 2-O-(Tetrahydro-2'-pyranyl)-1,2,4-butanetriol 
• 5469-16-9 4-Hydroxy-dihydro-furan-2-on 
• 108-88-3 toluene 
• 488-30-2 D-xylonic acid 
• 7724-28-9 (S)-hydroxy-succinaldehyde 
• 136264-10-3 ((R)-2-Isopropyl-[1,3]dioxan-4-yl)-methanol 
• 225933-67-5 (S)-4-ethoxy-2-hydroxy-4-oxobutanoic acid 
• 3068-00-6 D,L-1,2,4-butanetriol 
• 51267-44-8 (S)-3,4-dihydroxybutanoic acid 

Downstream Products

• 103708-37-8 (2S,4S)-4-hydroxymethyl-2-(p-methoxymethyl)-1,3-dioxane 
• 6414-28-4 (S)-1,2,4-butanetriol-1,2-cyclic carbonate 
• 32233-43-5 2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol 
• 95598-71-3 (S)-4-(2-benzoyloxy)ethyl-2,2-dimethyl-1,3-dioxolane 
• 86087-23-2 (S)-3-hydroxytetyrahydrofurane 
• 93464-99-4 3,5-Dinitro-benzoic acid (S)-2-(1,4-dioxa-spiro[4.5]dec-2-yl)-ethyl ester 
• 97678-48-3 (S)-1,4-bis-trityloxy-butan-2-ol 
• 85287-64-5 (S)-butane-1,2,4-triol 2,4-acetonide 
• 5055-10-7 (2S)-2-hydroxy-1,4-bis<(methansulfonyl)oxy>butane 
• 64028-90-6 (S)-1,4-dibromo-2-butanol 
• 114818-97-2 (S)-1,4-dibenzyloxy-2-butanol 
• 256390-84-8 (S)-4-(hydroxymethyl)-2-phenyl-1,3-dioxane 
• 187102-96-1 2-((S)-2-Phenyl-[1,3]dioxolan-4-yl)-ethanol 
• 125758-71-6 C₄₆H₄₆O₇ 

Relevant articles and documents

Blasticidin A as an inhibitor of aflatoxin production by Aspergillus parasiticus

Blasticidin A, an antibiotic, showed strong inhibitory activity toward aflatoxin production by Aspergillus parasiticus. Its structure was characterized by NMR and chemical degradation experiments as 1, which is a tetramic acid derivative with a highly oxygenated long alkyl chain similar to aflastatin A (2). Absolute configurations of the eight chiral centers at C-4, 6, 31, 32, 33, 34, 35 and 37 of 1 were chemically determined. Blasticidin A almost completely inhibited aflatoxin production at 0.5 μm.

Development of an Efficient Process for the Decomposition of the Borate Complexes Formed during the Large-Scale Synthesis of (S)-1,2,4-Butanetriol

An improved multikilogram-scale process for the production of (S)-1,2,4-butanetriol has been developed. This process involves the efficient removal of residual boric acid and the decomposition of the borate complexes formed during the reduction of (-)-dimethyl malate with sodium borohydride by methanolysis using a circular distillation-coupled hydrolysis apparatus.

Optically active isonitrile ligand for palladium-catalyzed enantioselective bis-silylation of carbon-carbon double bonds

Intramolecular bis-silylation of homoallylic alcohols proceeded enantioselectively in the presence of a catalyst prepared from Pd(acac), and optically active isonitriles, derived from a common chiral source, (+)-ketopinic acid.

IMMUNOMODULATORY GLYCOSPHINGOLIPIDS AND METHODS OF USE THEREOF

Provided herein are a subset of alpha-galactosylceramide (alpha-GC) compounds having improved immunomodulatory activity, particularly with respect to NKT cell number and activity. Also provided herein are methods of use of such compounds, including in the modulation of NKT cells and/or activity in vivo. Further provided are combinatorial synthesis methods for generating alpha-GC compounds of specifically defined structure and thereby generating pure preparations thereof.

Synthesis of a C1-C12 Fragment of Gulmirecin B

The synthesis of a C1-C14 fragment of the macrolide antibiotic gulmirecin B through formation of the C7-C8 bond by addition of a vinyllithium intermediate to a C1-C7 aldehyde was investigated. This crucial coupling was successful with a vinyllithium reagent corresponding to a C8-C12 fragment. The C8-C12 vinyl bromide was prepared from l -malic acid. The C1-C7 aldehyde building block was synthesized from hex-5-enoic acid by using an Evans alkylation, a cross-metathesis, and an asymmetric dihydroxylation as key steps.