29514-28-1

Basic information

• Product Name: 1,2-O-Isopropylidene--L-idofuranuronic Acid -Lactone
• Synonyms: 1,2-O-(1-Methylethylidene)--L-idofuranuronic Acid -Lactone;1,2-O-Isopropylidene--L-idofuranuronic Acid -Lactone;1,2-O-Isopropylidene--L-idofuranurono-6,3-lactone;1,2-O-Isopropylidene-b-L-idofuranosylurono-6,3-lactone;1,2-O-Isopropylidene-beta-L-idofuranuronic acid, gamma-lactone min. 99%;beta-L-Idofurano-6,3-lactone acetonide, beta-L-Iduronolactone acetonide;(1S,2R,6R,8R,9R)-9-Hydroxy-4,4-dimethyl-3,5,7,11-tetraoxatricyclo[6.3.0.02,6]undecan-10-one
• CAS NO: 29514-28-1
• Molecular Formula: C₉H₁₂O₆
• Molecular Weight: 216.18798
• Product Categories: Carbohydrates & Derivatives;Chiral Reagents;Heterocycles;Chiral Reagents, Heterocycles, Carbohydrates & Derivatives
• Mol File: 29514-28-1.mol
• Article Data: 32

Chemical Properties

• Melting Point: 104-107°C
• Appearance: /
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility: Acetone, Chloroform
• CAS DataBase Reference: 1,2-O-Isopropylidene--L-idofuranuronic Acid -Lactone(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-O-Isopropylidene--L-idofuranuronic Acid -Lactone(29514-28-1)
• EPA Substance Registry System: 1,2-O-Isopropylidene--L-idofuranuronic Acid -Lactone(29514-28-1)

Safety Data

• Hazardous Substances Data: 29514-28-1(Hazardous Substances Data)

Usage

Description

1,2-O-Isopropylidene-β-L-idofuranurono-6,3-lactone, with the CAS number 29514-28-1, is an off-white solid compound that is useful in organic synthesis. It is a derivative of L-idofuranuronic acid, featuring an isopropylidene protecting group that can be selectively removed under mild acidic conditions, making it a versatile intermediate in the synthesis of various complex carbohydrates and related compounds.

Uses

Used in Organic Synthesis:
1,2-O-Isopropylidene-β-L-idofuranurono-6,3-lactone is used as a versatile intermediate in organic synthesis for the preparation of complex carbohydrates and related compounds. Its isopropylidene protecting group allows for selective deprotection under mild acidic conditions, facilitating the synthesis of target molecules with specific structural features.
Used in Pharmaceutical Industry:
1,2-O-Isopropylidene-β-L-idofuranurono-6,3-lactone is used as a key building block in the synthesis of pharmaceutical compounds, particularly those with carbohydrate moieties. Its unique chemical properties enable the development of novel drug candidates with potential therapeutic applications.
Used in Material Science:
1,2-O-Isopropylidene-β-L-idofuranurono-6,3-lactone is used as a component in the development of advanced materials, such as polymers and coatings, that incorporate carbohydrate structures. Its chemical versatility allows for the creation of materials with tailored properties for specific applications.
Used in Research and Development:
1,2-O-Isopropylidene-β-L-idofuranurono-6,3-lactone is used as a research tool in the study of carbohydrate chemistry, enabling scientists to explore the synthesis and properties of complex carbohydrate structures. Its unique features make it an invaluable compound for advancing our understanding of carbohydrate-based systems.

Upstream product

• 32449-92-6 D-glucurono-6,3-lactone 
• 2671-19-4 O¹,O²-isopropylidene-α-D-glucofuranuronic acid 
• 5206-40-6 5-O-acetyl-1,2-O-isopropylidene-β-L-idofuranurono-6,3-lactone 
• 5111-13-7 (1S,3R,4R,5S,8S)-8-benzyloxy-7-keto-3,4-isopropylidenedioxy-2,6-dioxabicyclo[3.3.0]octane 
• 63-29-6 D-glucurono-6,3-lactone 
• 67-64-1 acetone 
• 14362-29-9 α-D-glucurono-γ-lactone 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 575-64-4 D-mannofuranurono-6,3-lactone 
• 63-29-6 L-glucurono-3,6-lactone 
• 15397-08-7 D-glycero-D-galacto-heptono-1,4-lactone 
• 3067-56-9 isopropylidene glucuronolactone 

Downstream Products

• 55263-78-0 1,2-O-isopropylidene-5-O-toluene-p-sulphonyl-α-D-glucofuranurono-6,3-lactone 
• 50-99-7 D-glucose 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 50767-75-4 methyl 3,5-O-benzylidene-1,2-O-isopropylidene-α-D-glucofuranuronate 
• 138610-59-0 N-(p-methoxybenzyl)-1,2-isopropylidene-D-glucofuranuronamide 
• 170872-96-5 (+)-1,2-O-Isopropylidene-5-O-(phenoxythiocarbonyl)-α-D-glucurono-6,3-lactone 
• 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 
• 6984-47-0 C₁₆H₁₆O₇ 
• 59957-59-4 methyl 5-O-benzoyl-1,2-O-isopropylidene-α-D-glucuronate 
• 60480-34-4 C₁₇H₁₈O₈ 
• 952058-04-7 methyl (Z)-5-O-benzoyl-3-deoxy-3-C[(ethoxycarbonyl)methylene]-1,2-O-isopropylidene-α-D-penturonate 
• 911407-82-4 (6R)-3-benzyloxyimino-1,2:5,6-di-O-isopropylidene-6-(prop-2-ynyl)-α-D-ribohexofuranose 
• 911407-81-3 (6R)-3-benzyloxyimino-1,2:5,6-di-O-isopropylidene-6-(3-trimethylsilyl-prop-2-ynyl)-α-D-ribohexofuranose 

Relevant articles and documents

Method for preparing eribulin dehydroxylation intermediate by one-pot method

The invention relates to the technical field of organic synthesis, in particular to a method for preparing an eribulin dehydroxylation intermediate by a one-pot method, which comprises the following steps of in an organic solvent, taking a compound I as a raw material, carrying out oxidation-reduction reaction on the compound I, a reducing agent, a catalyst and alkali, and separating and purifying reaction liquid to obtain a compound as shown in a formula II, namely the eribulin dehydroxylation intermediate. According to the method disclosed by the invention, sulfonyl chloride, Pd/C, iodine elementary substance and pyridine which are not green and are high in price are not used, but cheap and green reagents are adopted for replacement, so that the greenness, the economical efficiency and the safety of the reaction are remarkably improved. The reaction efficiency is greatly improved and the reaction cost is reduced by shortening the reaction steps and the reaction time.

Synthesis of 1,3,4,6-Tetra-O-acetyl-l-gulose

A novel, practical and concise synthesis of 1,3,4,6-tetra-O-acetyl-l-gulose is described, using d-glucuronolactone as the starting material and other inexpensive and readily available agents (22% overall yield in 9 steps). With this method, the synthesis of l-gulose and the tumor-targeting disaccharide of BLMs can be more efficient and convenient.

Synthesis of purine nucleosides from D -glucuronic acid derivatives and evaluation of their cholinesterase-inhibitory activities

Glucuronolactones were used as precursors for N9 and N 7 purine nucleosides containing glucuronic acid derivatives in their structures. Acetylated N-benzylglucofuran- and glucopyranuronamides were synthesized in a few steps from glucofuranurono-6,3-lactone. They were converted into the corresponding furanosyl and pyranosyl uronamide-based nucleosides by N-glycosylation with silylated 2-acetamido-6-chloropurine in the presence of trimethylsilyl triflate. The triacetylated bicyclic lactone was coupled itself with the nucleobase to give bicyclic N9,N7 nucleosides. Tri-O-acetylglucopyranurono-6,1-lactone was used for the first time as a glycosyl donor for N-glycosylation, and led to β-configured N9- and N7-linked purinylglucuronides under reaction conditions similar to those used with the 1-O-acetyl-substituted glycosyl donors. The cholinesterase inhibitory profiles of the synthetic nucleosides bearing glucuronic acid derivatives as glycons were evaluated, and they showed moderate selective acetylcholinesterase inhibitory activities (Ki = 14.78-50.53 μM). The best inhibition was shown by the furanosyl N 9-linked uronamide-based purine nucleoside. The synthesis of furanosyl and pyranosyl N9 and N7 purine nucleosides containing glucofuranurono-6,3-lactone, N-benzylglucuronamide, and glucuronic acid moieties is reported. Glucuronolactones were used as glycosyl donors or converted into suitable 1-O-acetyl derivatives for purine glycosylation. Some nucleosides showed moderate and selective inhibition of acetylcholinesterase. Copyright