20513-98-8

Basic information

• Product Name: D-Glucurono-6,3-lactone acetonide
• Synonyms: D-GLUCURONO-6,3-LACTONE ACETONIDE;6,3-GLUCURONOLACTONE ACETONIDE;1,2-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANURONO-6,3-LACTONE;1,2-O-ISOPROPYLIDENE-ALPHA-D-GLUCURONO-6,3-LACTONE;.alpha.-D-Glucofuranuronic acid, 1,2-O-(1-methylethylidene)-, .gamma.-lactone;1,2-O-Isopropylidene-a-D-glucofuranurono-6,3-lactone;1,2-O-(1-Methylethylidene)-α-D-glucofuranuronic Acid -Lactone;1,2-O-Isopropylidene-α-D-glucofuranosidurono-6,3-lactone
• CAS NO: 20513-98-8
• Molecular Formula: C₉H₁₂O₆
• Molecular Weight: 216.19
• EINECS: -0
• Product Categories: Chiral Reagents;Biochemistry;Glucose;Sugar Acids;Sugars;Carbohydrates & Derivatives;Heterocycles
• Mol File: 20513-98-8.mol
• Article Data: 39

Chemical Properties

• Melting Point: 119-121°C
• Boiling Point: 385.994 °C at 760 mmHg
• Flash Point: 158.842 °C
• Appearance: /
• Density: 1.411 g/cm³
• Vapor Pressure: 1.5E-07mmHg at 25°C
• Refractive Index: 1.51
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Water (Slightly)
• PKA: 12.09±0.40(Predicted)
• CAS DataBase Reference: D-Glucurono-6,3-lactone acetonide(CAS DataBase Reference)
• NIST Chemistry Reference: D-Glucurono-6,3-lactone acetonide(20513-98-8)
• EPA Substance Registry System: D-Glucurono-6,3-lactone acetonide(20513-98-8)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 20513-98-8(Hazardous Substances Data)

Usage

Description

D-Glucurono-6,3-lactone acetonide, also known as 1,2-O-Isopropylidene-α-D-glucofuranosidurono-6,3-lactone, is an organic compound with the CAS number 20513-98-8. It is a derivative of D-glucuronic acid, featuring a lactone ring and an acetonide protecting group. D-Glucurono-6,3-lactone acetonide is significant in the field of organic synthesis due to its unique structural properties and reactivity.

Uses

Used in Organic Synthesis:
D-Glucurono-6,3-lactone acetonide is used as an intermediate in organic synthesis for the preparation of various complex molecules and biologically active compounds. Its unique structure allows for selective functionalization and manipulation in chemical reactions, making it a valuable building block in the synthesis of pharmaceuticals, natural products, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, D-Glucurono-6,3-lactone acetonide is used as a key component in the development of novel drug candidates. Its ability to form diverse chemical structures makes it a promising starting material for the design and synthesis of new therapeutic agents, particularly those targeting specific biological pathways or receptors.
Used in Research and Development:
D-Glucurono-6,3-lactone acetonide is also utilized in research and development settings, where it serves as a model compound for studying the properties and reactivity of similar structures. This helps chemists to better understand the underlying mechanisms of various chemical reactions and to develop more efficient synthetic routes for the production of target molecules.

InChI:InChI=1/C9H12O6/c1-9(2)14-6-5-4(13-8(6)15-9)3(10)7(11)12-5/h3-6,8,10H,1-2H3

Upstream product

• 5206-40-6 5-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranurono-6,3-lactone 
• 50767-75-4 methyl 3,5-O-benzylidene-1,2-O-isopropylidene-β-L-idofuranuronate 
• 3067-56-9 isopropylidene glucuronolactone 
• 63-29-6 L-glucurono-3,6-lactone 
• 67-64-1 acetone 
• 575-64-4 D-mannofuranurono-6,3-lactone 
• 50767-75-4 methyl 3,5-O-benzylidene-1,2-O-isopropylidene-α-D-glucofuranuronate 
• 3067-56-9 D-glucurono-3,6-lactone acetonide 
• 14362-29-9 α-D-glucurono-γ-lactone 
• 103357-81-9 Trifluoro-methanesulfonic acid (3aR,3bS,6R,6aS,7aR)-2,2-dimethyl-5-oxo-hexahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxol-6-yl ester 
• 29747-91-9 1,2-O-isopropylidene-β-L-idofuranose 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 487-44-5 D-(+)-glucuronic acid γ-lactone 
• 25531-72-0 1,2-O-isopropylidene-α-D-gluco-hexodialdo-1,4:6,3-difuranose 

Downstream Products

• 3067-56-9 (3aR,6R,7aR)-6-Hydroxy-2,2-dimethyl-tetrahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxol-5-one 
• 183371-82-6 (3aR,3bS,5R,6S,6aR,7aR)-2,2-Dimethyl-5-phenyl-hexahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxole-5,6-diol 
• 5111-13-7 (1S,3R,4R,5S,8S)-8-benzyloxy-7-keto-3,4-isopropylidenedioxy-2,6-dioxabicyclo[3.3.0]octane 
• 173066-60-9 (2R,4R,4aS,7R,7aR)-4-(Bis-ethylsulfanyl-methyl)-7-hydroxy-2-(4-methoxy-phenyl)-tetrahydro-furo[3,2-d][1,3]dioxin-6-one 
• 173066-68-7 (R)-2-[(2R,4S,5S,6R)-6-(Bis-ethylsulfanyl-methyl)-5-hydroxy-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-2-hydroxy-N-methyl-acetamide 
• 173066-64-3 Benzoic acid (1S,2R)-1-((1R,2R)-1-benzyloxy-2-hydroxy-2-methylcarbamoyl-ethyl)-3,3-bis-ethylsulfanyl-2-(4-methoxy-benzyloxy)-propyl ester 
• 173066-69-8 (R)-2-[(2R,4S,5S,6R)-6-(Bis-ethylsulfanyl-methyl)-5-hydroxy-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-2-(tert-butyl-diphenyl-silanyloxy)-N-methyl-acetamide 
• 173066-61-0 Benzoic acid (1S,2S,3R)-1-[(R)-2,2-bis-ethylsulfanyl-1-(4-methoxy-benzyloxy)-ethyl]-3-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-3-methylcarbamoyl-propyl ester 
• 173066-59-6 Benzoic acid (2R,4R,5S,6S)-4-(bis-ethylsulfanyl-methyl)-6-[(R)-(tert-butyl-diphenyl-silanyloxy)-methylcarbamoyl-methyl]-2-(4-methoxy-phenyl)-[1,3]dioxan-5-yl ester 
• 173066-62-1 Benzoic acid (1S,2S,3R)-2-benzyloxy-1-[(R)-2,2-bis-ethylsulfanyl-1-(4-methoxy-benzyloxy)-ethyl]-3-(tert-butyl-diphenyl-silanyloxy)-3-methylcarbamoyl-propyl ester 
• 116393-60-3 Sodium; (2aS,2bR,5aR,6aS)-4,4-dimethyl-tetrahydro-2,3,5,6-tetraoxa-cyclobuta[a]pentalene-1-carboxylate 
• 1285718-32-2 C₁₆H₁₆O₇ 
• 1394245-95-4 C₁₆H₁₈O₆ 

Relevant articles and documents

Attempted synthesis of the imidazylate of an α-hydroxylactone results in unexpected chlorination: Synthesis and X-ray crystal structure of 5-Chloro-5-deoxy-1,2- O -isopropylidene-β- l -idurono-6,3-lactone

Attempted synthesis of the imidazylate derivative of 1,2-O-isopropylidene- α-D-glucurono-6,3-lactone (2) via treatment with sulfuryl chloride in the presence of excess imidazole in DMF at either -40°C or -70°C resulted in the unexpected formation of 5-chloro-5-deoxy-1,2-O-isopropylidene-β-l- idurono-6,3-lactone (7). Chloride 7 presumably forms via the rapid S N2 displacement by a chloride ion of an initially formed chlorosulfate ester intermediate, which is evidently unusually reactive. The identity of the product was confirmed by a single-crystal X-ray structure determination. Taylor & Francis Group, LLC.

A novel synthesis of L ascorbic acid

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Efficient Divergent Synthesis of 2′- O,4′- C-Ethylene-Bridged Nucleic Acid (ENA) Phosphoramidites

2′-O,4′-C-Ethylene-bridged nucleic acid (ENA) phosphoramidites are highly promising modified nucleic acid monomers discovered by Daiichi Sankyo. To increase the productivity of manufacturing, we have developed a highly efficient synthetic method for ENA phosphoramidites. The basic concept of the new synthetic route is "divergent synthesis"for the preparation of four types of monomers such as A, G, C, and T. We applied stereoselective glycosylation reactions without utilizing neighboring group participation to set a common intermediate in the downstream of the route.

INTERMEDIATES FOR THE PREPARATION OF ERIBULIN THEREOF

The present invention relates to novel intermediates of Eribulin and process for the preparation of the same. The process of the present invention is commercially viable and can be easily adopted for plant scale operations. The present invention relates to tetrahydrofuran compounds of formula I, X, XI, D and B.