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

Uses

Different sources of media describe the Uses of 25581-41-3 differently. You can refer to the following data:
1. As a chiral synthon, 2,3-O-Isopropylidene-D-erythronolactone can be used for the synthesis of certain natural products such as the leukotrienes.
2. It undergoes Aldol condensations with silyl ketene acetals.1 Employed in spiroannulated carbohydrate synthesis.2 Convergent syntheses of a hydroxylated indolizidine,3 carbohydrate substituted benzoquinones,4 and of the oxazole segment of calyculin5 have been accomplished using this chiral synthon.
3. Undergoes Aldol condensations with silyl ketene acetals. Employed in spiroannulated carbohydrate synthesis. Convergent syntheses of a hydroxylated indolizidine, carbohydrate substituted benzoquinones, and of the oxazole segment of calyculin have been accomplished using this chiral synthon.

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

• 137664-58-5 (4R,5R)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid 4-methoxy-benzylamide 
• 174498-51-2 (3aR,6aR)-2,2-Dimethyl-4-phenyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ol 
• 384331-56-0 (4R,5R)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid (2-bromo-phenyl)-amide 
• 717920-96-2 (4R,5R)-5-(hydroxymethyl)-2,2-dimethyl-N-(phenylmethoxy)-1,3-dioxolane-4-carboxamide 
• 133634-83-0 2,5-anhydro-1-deoxy-3,4-O-isopropylidene-D-erythro-pent-1-enitol 
• 603959-03-1 (4R,5S)-[5-(benzylaminomethyl)-2,2-dimethyl[1,3]dioxolan-4-yl]methanol 
• 581777-37-9 ((4S,5R)-5-Aminomethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-benzyl-carbamic acid tert-butyl ester 
• 581777-36-8 Methanesulfonic acid (4R,5S)-5-[(benzyl-tert-butoxycarbonyl-amino)-methyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 
• 85624-09-5 (3aR,9R,9aR,9bS)-octahydro-2,2-dimethyl-[1,3]dioxolo[4,5-a]indolizin-9-ol 
• 1026627-80-4 C₂₂H₂₆BrNO₆ 
• 15667-21-7 D-erythronolactone 
• 850359-46-5 3,4-O-isopropylidene-2-C-methyl-D-arabinono-1,5-lactone 
• 492-30-8 2-C-methyl-D-ribono-1,4-lactone 
• 53008-90-5 2-C-methyl-D-arabino-γ-lactone 

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.