18968-51-9

Basic information

• Product Name: (3aS,5S,6R,6aS)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde
• CAS NO: 18968-51-9
• Molecular Weight: 202.207
• Mol File: 18968-51-9.mol
• Article Data: 15

Chemical Properties

• CAS DataBase Reference: (3aS,5S,6R,6aS)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: (3aS,5S,6R,6aS)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde(18968-51-9)
• EPA Substance Registry System: (3aS,5S,6R,6aS)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde(18968-51-9)

Safety Data

• Hazardous Substances Data: 18968-51-9(Hazardous Substances Data)

Upstream product

• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 2595-05-3 Diacetone D-glucose 
• 29587-01-7 5-[2,2-dimethyl-(4R)-1,3-dioxolan-4-yl]-2,2-dimethyl-(3aR,5R,6R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-6-yl methyl ether 
• 18968-50-8 1-[6-methoxy-2,2-dimethyl-(3aR,5R,6R,6aR)-perhydrofuro-[2,3-d][1,3]dioxol-5-yl]-(1R)-ethane-1,2-diol 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 
• 492-62-6 alpha-D-glucopyranose 
• 50-99-7 D-glucose 
• 2280-44-6 D-Glucose 
• 18968-50-8 3'-O-methyl-1,2-O-isopropylidene-α-D-glucofuranose 
• 350255-13-9 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 35506-61-7 ((3aR,5R,6S,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-methanol 
• 43138-64-3 1,2-:5,6-di-O-isopropylidene-3-O-methyl-α-D-glucofuranose 
• 43138-65-4 1,2-O-isopropylidene-3-O-methyl-α-D-glucofuranose 

Downstream Products

• 35506-61-7 ((3aR,5R,6S,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-methanol 
• 58707-34-9 5-O-benzoyl-3-O-methyl-1,2-O-isopropylidene-α-D-xylofuranose 

Relevant articles and documents

Novel: O -methyl goniofufurone and 7- epi -goniofufurone derivatives: Synthesis, in vitro cytotoxicity and SAR analysis

Novel goniofufurone (1) and 7-epi-goniofufurone (2) derivatives bearing a methoxy group at the C-5 and/or C-7 positions were prepared and their in vitro antitumour activity against some human tumour cell lines was evaluated. Some of the analogues displayed powerful antiproliferative effects against the studied tumour cells, but almost all of them were non-cytotoxic toward the normal cells (MRC-5). A SAR study reveals that the introduction of a methoxy group at the C-7 position may increase the antiproliferative effects of the analogues. The most active compounds are 7-O-methyl derivatives of goniofufurone (3) and 7-epi-(+)-goniofufurone (6), which exhibited 1177- and 451-fold higher potencies than the leads 1 and 2 toward the MDA-MB 231 cell line. At the same time, compound 3 is almost 1.5-fold more active than the commercial drug doxorubicin (DOX) against the same cell line. Flow cytometry data confirmed that the cytotoxic effects of these analogues are mediated by apoptosis, additionally revealing that these molecules induced changes in the K562 cell cycle distribution.

NHC-Catalyzed Dual Stetter Reaction: A Mild Cascade Annulation for the Syntheses of Naphthoquinones, Isoflavanones, and Sugar-Based Chiral Analogues

The N-heterocycle carbene (NHC)-catalyzed dual Stetter cascade reaction is discovered through coupling of β-nitrostyrene with phthalaldehyde under mild conditions to furnish valuable aryl-naphthoquinones. The generality of the new reaction is validated through the development of a C-C and O-C bond forming Stetter cascade reaction using salicylaldehydes to obtain functionalized dihydroisoflavanones. The mild NHC organocatalysis is successfully employed for the construction of optically pure sugar-based naphthoquinones and dihydroisoflavanones. Herein, NHC is found as a unique and powerful organocatalyst to construct homoatomic C-C cross-coupling, heteroatomic O-C bond formation, and cascade cyclization utilizing NO2 as a leaving group at ambient temperature. A mechanistic pathway of the new metal-free catalysis is predicted on the basis of our ESI-MS study of the ongoing reaction and literature.

I2/PPh3-mediated facile synthesis of glycoconjugated N-acylbenzotriazoles

A well-stabilized method for synthesis of N-acylbenzotriazoles from carboxylic acids using I2/PPh3 in anhydrous dichloromethane has been extended in glycochemistry to synthesize glycoconjugated N-acylbenzotriazoles with high yields at room temperature in 2-hour reaction time.