25581-41-3

Basic information

• Product Name: 2,3-O-ISOPROPYLIDENE-D-ERYTHRONOLACTONE
• Synonyms: 2,3-O-ISOPROPYLIDENE-D-ERYTHRONOLACTOL;(-)-2,3-O-ISOPROPYLIDENE-D-ERYTHRONO-LACTONE;2,3-O-ISOPROPYLIDENE-D-ERYTHRONOLACTONE;Furo[3,4-d]-1,3-dioxol-4(3aH)-one, dihydro-2,2-dimethyl-, (3aR,6aR)-;(-)-2,3-O-Isopropylidene-D-erythronolactone;(3aR,6aR)-Dihydro-2,2-diMethyl-furo[3,4-d]-1,3-dioxol-4(3aH)-one;D-2,3-O-Isopropylidene-erythronic Acid γ-Lactone;(-)-2,3-O-Isopropylidene-D-erythronolactone 98%
• CAS NO: 25581-41-3
• Molecular Formula: C₇H₁₀O₄
• Molecular Weight: 158.15
• Product Categories: Chiral Reagents;Biochemistry;Erythrose;O-Substituted Sugars;Sugar Acids;Sugars;Carbohydrate Synthesis;Monosaccharides;Specialty Synthesis;Heterocycles
• Mol File: 25581-41-3.mol
• Article Data: 13

Chemical Properties

• Melting Point: 67-69 °C(lit.)
• Boiling Point: 259.7 °C at 760 mmHg
• Flash Point: 112.4 °C
• Appearance: White to Off-white/Powder
• Density: 1.207 g/cm³
• Vapor Pressure: 0.0128mmHg at 25°C
• Refractive Index: -117 ° (C=1, H2O)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform (Slightly), Water (Slightly)
• Water Solubility: Soluble in water
• BRN: 1282952
• CAS DataBase Reference: 2,3-O-ISOPROPYLIDENE-D-ERYTHRONOLACTONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-O-ISOPROPYLIDENE-D-ERYTHRONOLACTONE(25581-41-3)
• EPA Substance Registry System: 2,3-O-ISOPROPYLIDENE-D-ERYTHRONOLACTONE(25581-41-3)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 25581-41-3(Hazardous Substances Data)

Usage

Description

2,3-O-Isopropylidene-D-erythronolactone is a chiral synthon that serves as a key intermediate in the synthesis of various natural products and complex molecules. It is characterized by its unique structure and reactivity, making it a valuable compound in organic chemistry and pharmaceutical research.

Uses

Used in Pharmaceutical Industry:
2,3-O-Isopropylidene-D-erythronolactone is used as a chiral synthon for the synthesis of certain natural products, such as leukotrienes. Its unique structure allows for the creation of complex molecules with potential therapeutic applications.
Used in Organic Chemistry:
2,3-O-Isopropylidene-D-erythronolactone is used as a chiral synthon for undergoing Aldol condensations with silyl ketene acetals. This reaction is crucial in the synthesis of various complex molecules, including spiroannulated carbohydrates.
Used in Carbohydrate Chemistry:
In carbohydrate chemistry, 2,3-O-Isopropylidene-D-erythronolactone is employed in the synthesis of spiroannulated carbohydrates, which have potential applications in drug development and material science.
Used in Natural Product Synthesis:
This chiral synthon has been utilized in the convergent syntheses of a hydroxylated indolizidine, carbohydrate-substituted benzoquinones, and the oxazole segment of calyculin, which are complex natural products with diverse biological activities.

InChI:InChI=1/C7H10O4/c1-7(2)10-4-3-9-6(8)5(4)11-7/h4-5H,3H2,1-2H3

Upstream product

• 77-76-9 2,2-dimethoxy-propane 
• 15667-21-7 D-erythronolactone 
• 67-64-1 acetone 

Downstream Products

• 189996-60-9 2,3-O-isopropylidene-D-erythrose 
• 137664-58-5 (4R,5R)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid 4-methoxy-benzylamide 
• 23918-98-1 eritadenine 
• 51607-16-0 2,3-O-isopropylidene-D-erythrose 
• 23262-84-2 (3aS,6aS)-2,2-Dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ol 
• 174498-51-2 (3aR,6aR)-2,2-Dimethyl-4-phenyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ol 
• 127758-25-2 (4R,5S)-(2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)methan-1-ol 
• 109947-62-8 1-deoxy-3,4-O-isopropylidene-β-D-erythro-pent-2,5-furanosulose 
• 133634-83-0 2,5-anhydro-1-deoxy-3,4-O-isopropylidene-D-erythro-pent-1-enitol 
• 384331-56-0 (4R,5R)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid (2-bromo-phenyl)-amide 
• 471931-09-6 (4R,5R)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid benzylamide 
• 717920-96-2 (4R,5R)-5-(hydroxymethyl)-2,2-dimethyl-N-(phenylmethoxy)-1,3-dioxolane-4-carboxamide 
• 873299-99-1 (3aR,6aR)-2,2-Dimethyl-4-((E)-3-phenyl-allyloxy)-tetrahydro-furo[3,4-d][1,3]dioxole 

Relevant articles and documents

Toward the stereoselective synthesis of zaragozic acid framework: A desilylation-aldol reaction approach

A convergent synthesis of the C3-C8 fragment of zaragozic acids is described. The key reactions include desilylation-aldol reaction, rearrangement induced by regioselective reductive cleavage, BAIB/TEMPO-Pinnick oxidation, esterification, silylation, and hydrogenolysis.

Synthetic studies towards an advanced precursor of the jatrophane diterpene Pl-4

Jatrophane diterpenes, isolated from members of the Euphorbiaceae plant family, constitute a class of biologically and structurally intriguing natural products. Herein, different strategies for the preparation of an advanced intermediate towards the total synthesis of the jatrophane diterpene Pl-4 are described. Key strategies for the elaboration of the jatrophane precursors include hydrometalation and radical reactions. Georg Thieme Verlag KG Stuttgart · New York.

Carbon-branched carbohydrate chirons: practical access to both enantiomers of 2-C-methyl-ribono-1,4-lactone and 2-C-methyl-arabinonolactone

Readily crystallized 2-C-methyl-d-ribono-1,4-lactone is formed in a one-pot procedure from d-glucose without any protecting groups by treatment with dimethylamine to give an Amadori ketose and then with aqueous calcium hydroxide in yields of approximately 25%; 2-C-methyl-l-ribono-1,4-lactone is similarly produced from l-glucose. 3,4-O-Isopropylidene-2-C-methyl-d-arabinono-1,5-lactone and 2-C-methyl-d-arabinono-1,4-lactone were prepared in a combined 60% yield by the Kiliani reaction of sodium cyanide with a protected 1-deoxy-d-ribulose derived from d-erythronolactone; the enantiomeric arabinonolactones are similarly available from l-erythronolactone.