3067-56-9

Basic information

• Product Name: (3aR,6R,7aR)-6-Hydroxy-2,2-dimethyl-tetrahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxol-5-one
• CAS NO: 3067-56-9
• Molecular Weight: 216.191
• Mol File: 3067-56-9.mol
• Article Data: 32

Chemical Properties

• CAS DataBase Reference: (3aR,6R,7aR)-6-Hydroxy-2,2-dimethyl-tetrahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxol-5-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3aR,6R,7aR)-6-Hydroxy-2,2-dimethyl-tetrahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxol-5-one(3067-56-9)
• EPA Substance Registry System: (3aR,6R,7aR)-6-Hydroxy-2,2-dimethyl-tetrahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxol-5-one(3067-56-9)

Safety Data

• Hazardous Substances Data: 3067-56-9(Hazardous Substances Data)

Upstream product

• 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 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 67-64-1 acetone 
• 575-64-4 D-mannofuranurono-6,3-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 
• 14362-29-9 α-D-glucurono-γ-lactone 
• 63-29-6 D-glucurono-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 
• 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 
• 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 
• 89755-56-6 <3aR(3aα,5β,6β,6aα)>-tetrahydro-2,2-dimethyl-5-(2-propen-1-yl)-6-(phenylmethoxy)furo<2,3-d>-1,3-dioxole 
• 19130-96-2 1,5-dideoxy-1,5-imino-D-glucitol 
• 104154-10-1 N-(5-carboxypentyl)deoxynojirimycin 

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.

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.