85080-95-1

Basic information

• Product Name: 1,2-O-Isopropylidene-betaD-idofuranurono-6,3-lactone
• CAS NO: 85080-95-1
• Molecular Weight: 216.191
• Mol File: 85080-95-1.mol
• Article Data: 32

Chemical Properties

• CAS DataBase Reference: 1,2-O-Isopropylidene-betaD-idofuranurono-6,3-lactone(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-O-Isopropylidene-betaD-idofuranurono-6,3-lactone(85080-95-1)
• EPA Substance Registry System: 1,2-O-Isopropylidene-betaD-idofuranurono-6,3-lactone(85080-95-1)

Safety Data

• Hazardous Substances Data: 85080-95-1(Hazardous Substances Data)

Usage

Molecular weight

218.20 g/mol

Appearance

White crystalline solid at room temperature

Derivative

Lactone derivative of D-galactose

Common uses

Protecting group for hydroxyl groups in carbohydrates and other organic molecules, intermediate in the synthesis of various pharmaceuticals and organic compounds

Stability

Relatively stable

Toxicity

Non-toxic

Upstream product

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

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 
• 50767-75-4 methyl 3,5-O-benzylidene-1,2-O-isopropylidene-α-D-glucofuranuronate 
• 55263-78-0 1,2-O-isopropylidene-5-O-toluene-p-sulphonyl-α-D-glucofuranurono-6,3-lactone 
• 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 
• 76542-58-0 5-O-benzoyl-1,2-O-isopropylidene-β-L-idofuranurono-6,3-lactone 
• 1285718-32-2 C₁₆H₁₆O₇ 
• 871347-98-7 (S)-3-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)propane-1,2-diol 
• 871347-97-6 C₁₇H₂₄O₆ 
• 96687-98-8 [3aR,4aR,7aS,7bR]-2,2-dimethylperhydrofuro[2,3:4,5]furo[2,3-d][1,3]dioxol-6(R/S)-ol 
• 35810-94-7 3,6-anhydro-5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose 
• 546141-37-1 (3aR,5R,6S,6aR)-5-allyl-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol 

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