15667-21-7

Basic information

• Product Name: D-ERYTHRONOLACTONE
• Synonyms: (2R,3R)-BUTANE-2,3,4-TRIOL-1,4 LACTONE;(3R)-CIS-4,5-DIHYDRO-3,4-DIHYDROXY-2(3H)-FURANONE;(3R-CIS) (-)-DIHYDRO-3,4-DIHYDROXY-2(3H)-FURANONE;(3R,4R)-(-)-D-ERYTHRONOLACTONE;(3R,4R)-DIHYDROXYDIHYDRO-2(3H)-FURANONE;D-ERYTHRONIC ACID GAMMA-LACTONE;D-ERYTHRONIC GAMMA-LACTONE;D-ERYTHRONOLACTONE
• CAS NO: 15667-21-7
• Molecular Formula: C₄H₆O₄
• Molecular Weight: 118.09
• Product Categories: chiral;Chiral Reagents;Biochemistry;Chiral Building Blocks;Erythrose;Simple Alcohols (Chiral);Sugar Acids;Sugars;Synthetic Organic Chemistry
• Mol File: 15667-21-7.mol
• Article Data: 23

Chemical Properties

• Melting Point: 100-102 °C(lit.)
• Boiling Point: 140.59°C (rough estimate)
• Flash Point: 129.12 °C
• Appearance: white to light yellow crystal powder
• Density: 1.0887 (rough estimate)
• Vapor Pressure: 0.00057mmHg at 25°C
• Refractive Index: -71 ° (C=1, H2O)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 12.34±0.40(Predicted)
• BRN: 81073
• CAS DataBase Reference: D-ERYTHRONOLACTONE(CAS DataBase Reference)
• NIST Chemistry Reference: D-ERYTHRONOLACTONE(15667-21-7)
• EPA Substance Registry System: D-ERYTHRONOLACTONE(15667-21-7)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 15667-21-7(Hazardous Substances Data)

Usage

Description

D-ERYTHRONOLACTONE, also known as D-erythrono-1,4-lactone, is a white to light yellow crystalline powder with potential applications in various industries due to its unique chemical properties. It is recognized as a chiral synthon and a potential substrate for dihydroxy acid dehydratase, making it a valuable compound for the synthesis of specific natural products.

Uses

Used in Pharmaceutical Industry:
D-ERYTHRONOLACTONE is used as a chiral synthon for the synthesis of certain natural products, such as the leukotrienes. Its role in the pharmaceutical industry is crucial for the development of new drugs and therapeutic agents that target various health conditions.
Used in Biochemical Research:
As a potential substrate of dihydroxy acid dehydratase, D-ERYTHRONOLACTONE plays a significant role in biochemical research. It aids in understanding the enzyme's function and its involvement in various metabolic pathways, which can lead to the discovery of novel treatments for specific diseases.
Used in Chemical Synthesis:
D-ERYTHRONOLACTONE's unique chemical properties make it an essential compound in chemical synthesis. It serves as a key building block for the creation of various complex molecules and compounds, contributing to the advancement of materials science and the development of new products with diverse applications.

Purification Methods

Recrystallise it from EtOAc (20 parts) or isoPrOH (3 parts). [Baker & MacDonald J Am Chem Soc 82 230 1960, Glattfeld & Forbrich J Am Chem Soc 56 1209 1934, Weidenhagen & Wegner Chem Ber 72 2010 1939, Musich & Rapoport J Am Chem Soc 100 4865 1978, Beilstein 18/2 V 457.]

InChI:InChI=1/C4H6O4/c5-2-1-8-4(7)3(2)6/h2-3,5-6H,1H2/t2-,3-/m1/s1

Upstream product

• 488-16-4 D-erythronic acid 
• 7152-74-1 (-)-(3R-cis)-mono(tetrahydro-4-hydroxy-2-oxo-3-furanyl)ester 2-(4-methyl-phenyl)hidrazide of ethanedioic acid 
• 134-03-2 Erythorbic acid 
• 141316-88-3 (2R,3S)-2,3-O-cyclohexylideneerythritol monoacetate 
• 89-65-6 isoascorbic acid 
• 488-16-4 (+/-)-erythronic acid 
• 2418-52-2 D-threitol 
• 909878-64-4 meso-erythritol 
• 50-81-7 ascorbic acid 
• 10323-20-3 D-Arabinose 
• 25581-41-3 D-erythronolactone acetonide 
• 219788-23-5 1,2:3,4-Di-O-isopropylidene-D-erythronic acid 
• 50-81-7 D-Isoascorbic acid 
• 164385-70-0 (R)-(tert-Butyl-dimethyl-silanyloxy)-((R)-2,2-diethyl-[1,3]dioxolan-4-yl)-acetic acid methyl ester 

Downstream Products

• 130412-79-2 (2R,3R)-2,3-bis(benzyloxy)-4-hydroxybutanoic acid 1,4-lactone 
• 136060-76-9 2-O-Tosyl-D-erythro-1,4-lactone 
• 136060-77-0 Toluene-4-sulfonic acid 2-oxo-2,5-dihydro-furan-3-yl ester 
• 25581-41-3 D-erythronolactone acetonide 
• 107-93-7 (E)-but-2-enoic acid 
• 7425-21-0 3-Iodo-n-butanoic acid 
• 488-16-4 D-erythronic acid 
• 1106929-66-1 2,3-O-methylidene-D-erythrono-1,4-lactone 
• 89299-65-0 methyl (2R,3R)-2,3,4-trihydroxybutanoate 
• 28617-15-4 O²,O³-dibenzoyl-DL-threonic acid-lactone 
• 40837-73-8 erythronic acid-(N'-phenyl-hydrazide) 
• 73713-13-0 D-erythronic acid amide 
• 40837-73-8 D-erythronic acid-(N'-phenyl-hydrazide) 
• 129083-02-9 (1S,2R)-1-(1H-benzimidazol-2-yl)-propane-1,2,3-triol 

Relevant articles and documents

Enzyme-catalyzed asymmetric synthesis; 10. Pseudomonas cepacia lipase mediated synthesis of enantiomerically pure (2R,3S)- and (2S,3R)-2,3-O-cyclohexylideneerythritol monoacetate from 2,3-O-cyclohexylideneerythritol

Pseudomonas cepacia lipase catalyzed hydrolysis of 2,3-O-cyclohexylideneerythritol diacetate in an emulsion of water and diisopropyl ether gives (2S,3R)-2,3-O-cyclohexylideneerythritol monoacetate [(2S,3R)-1-acetoxy-2,3-cyclohexylidenedioxy-4-hydroxybutane] with ≥ 99% ee in 91% yield by a preferential attack at the R-center CH2OAc group. The enantiomeric (2R,3S)-2,3-O-cyclohexylideneerythritol monoacetate is obtained by acetylation of 2,3-O-cyclohexylideneerythritol with vinyl acetate catalyzed by the same enzyme with ≥ 99% ee in 78% yield by a combined enantiotopos and enantiomer differentiation through a preferential attack at the R-center CH2OH groups.

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General Synthetic Approach to Rotenoids via Stereospecific, Group-Selective 1,2-Rearrangement and Dual S N Ar Cyclizations of Aryl Fluorides

A general synthetic approach to rotenoids is described, featuring 1) stereospecific, group-selective 1,2-rearrangements of epoxy alcohols, and 2) S N Ar oxy-cyclizations of aryl fluorides. The common intermediate epoxyketone, en route to (-)-rotenone and (-)-deguelin, was prepared from d -araboascorbic acid in five steps. Also described is the conversion of (-)-deguelin into oxidized congeners, (-)-tephrosin and (+)-12a- epi -tephrosin.

A method for synthesizing tetranoic acid

The invention discloses a synthetic method of tetronic acid. The synthetic method comprises the following steps: firstly oxidizing low-price easily-available natural sodium D-isoascorbate as a raw material through hydrogen peroxide, and acidifying through hydrochloric acid to prepare a key synthetic intermediate, namely erythronolactone; secondly, reacting erythronolactone with sulfonyl chloride to generate crude tetronic acid; finally, simply re-crystallizing obtained crude tetronic acid to obtain pure tetronic acid. The synthetic method has the characteristics of few synthetic steps, simple and convenient process, low synthetic cost, convenience for large-scale industrialized production and the like; finally obtained pure tetronic acid is high in yield and purity, the yield can reach more than 87%, and the purity can reach more than 99%.