10578-85-5

Basic information

• Product Name: 1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-RIBO-3-HEXOFURANOSE-3-ULOSE MONOHYDRATE
• Synonyms: 1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-RIBO-3-HEXOFURANOSE-3-ULOSE MONOHYDRATE;1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-RIBO-3-HEXULOFURANOSULOSE MONOHYDRATE;1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-RIBOHEXULOFURANOS-3-ULOSE HYDRATE;1,2:5,6-DI-O-ISOPROPYLIDINE-ALPHA-D-RIBO-HEXULOFURANOS-3-ULOSE HYDRATE;1,2:5,6 - Di-O-isopropylidene- a-D-ribo-hexulofuranos-3- ulose;1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-RIBO -3-HEXOFURANOSULOSE HYDRATE, TECH., 90%;1,2:5,6-Di-O-isopropylidine-a-D-ribo-hexulofuranos-3-ulosehydrate;1,2:5,6-Di-o-isopropylidene-alpha-D-ribo-3-hexulofuranose-3-ulose monohydrate
• CAS NO: 10578-85-5
• Molecular Formula: C₁₂H₂₀O₇
• Molecular Weight: 294.3
• Mol File: 10578-85-5.mol
• Article Data: 9

Chemical Properties

• Melting Point: 107-108 °C
• Boiling Point: 434.2±45.0 °C(Predicted)
• Appearance: /
• Density: 1.317±0.06 g/cm3(Predicted)
• PKA: 11.11±0.60(Predicted)
• CAS DataBase Reference: 1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-RIBO-3-HEXOFURANOSE-3-ULOSE MONOHYDRATE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-RIBO-3-HEXOFURANOSE-3-ULOSE MONOHYDRATE(10578-85-5)
• EPA Substance Registry System: 1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-RIBO-3-HEXOFURANOSE-3-ULOSE MONOHYDRATE(10578-85-5)

Safety Data

• Hazardous Substances Data: 10578-85-5(Hazardous Substances Data)

Usage

General Description

1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-RIBO-3-HEXOFURANOSE-3-ULOSE MONOHYDRATE is a chemical compound that is derived from the sugar ribose. It is commonly used as a protecting group in carbohydrate chemistry, as the isopropylidene group can be easily removed to reveal the free aldehyde or hydroxyl functionality. 1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-RIBO-3-HEXOFURANOSE-3-ULOSE MONOHYDRATE is often used in the synthesis of complex carbohydrates and glycosides, and its monohydrate form is more stable and easier to handle in laboratory settings. Overall, 1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-RIBO-3-HEXOFURANOSE-3-ULOSE MONOHYDRATE plays a crucial role in the development of new pharmaceuticals, bioactive compounds, and materials in various industries.

Upstream product

• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 
• 180627-08-1 O,O-diethyl 1,1-difluoro-1-bromomethane phosphonothioate 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 10578-95-7 (E/Z)-3-Deoxy-3-hydroxyimino-1,2:5,6-di-O-isopropylidene-α-D-ribohexofuranose 
• 65094-22-6 diethyl (bromodifluoromethyl)phosphonate 
• 1165952-91-9 cyclohexa-1,3-diene 
• 266306-47-2 3-chloro-3-deoxy-1,2:5,6-di-O-isopropylidene-3-C-nitroso-α-D-glucofuranose 

Downstream Products

• 14686-88-5 3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-erythro-hex-3-enofuranose 
• 111789-69-6 3'-acetyl-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-3a,6a-dihydro-2,2-dimethyl-5'-phenyl-spiro-1,3-dioxole-6(5H),2'(3'H)-<1,3,4>-oxadiazole> 
• 110089-62-8 3-O-acetyl-6-O-t-butyldimethylsilyl-1,2-O-isopropylidene-5-O-tosyl-α-D-allofuranose 
• 110089-63-9 Acetic acid (3aR,5S,6R,6aR)-5-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-2-(toluene-4-sulfonyloxy)-ethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 
• 110089-65-1 6-O-acetyl-1,2-O-isopropylidene-5-O-tosyl-α-D-allofuranose 
• 111789-68-5 1,2:5,6-di-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose benzoylhydrazone 

Relevant articles and documents

NMR spectroscopy and conformational analysis of 3-deoxy-3-C-(hydroxymethyl)-1,2:5,6-di-O-isopropylidene-α-D-allofuran ose

Homonuclear and heteronuclear 1- and 2-dimensional NMR techniques have been used to establish stereochemical and conformational relationships in the hydroxymethyl furanoside 2. Concurrent with the NMR studies, theoretical calculations were performed on this compound using computer-assisted model building (MacroModel) and molecular mechanics (MM2). From the NOE and J-coupling constraints obtained from NMR experiments, refined structures for this compound in two different solvents have been identified and optimized. The 'solvent effects' observed in the NMR spectra for 2 are interpreted in terms of the differences in the requirements for intramolecular electrostatic stabilization in the two solvents. Homonuclear and heteronuclear 1- and 2- dimensional NMR techniques have been used to establish stereochemical and conformational relationships in the hydroxymethyl furanoside 2. Concurrent with the NMR studies, theoretical calculations were performed on this compound using computer-assisted model building (MacroModel) and molecular mechanics (MM2). From the NOE and J-coupling constraints obtained from NMR experiments, refined structures for this compound in two different solvents have been identified and optimized. The ″solvent effects″ observed in the NMR spectra for 2 are interpreted in terms of the differences in the requirements for intramolecular electrostatic stabilization of the two solvents.

A practical access to glucose- and allose-based (5+5) 3- spiropseudonucleosides from a common intermediate

A practical access to glucose-based and allose-based spirooxazolidinones is reported. The synthetic sequence consisting of TEMPO-catalyzed oxidation of 1,2:5,6-di-O-isopropylidene-α-d-glucofuranose, Henry reaction, and reduction provides amino alcohol with allo-configuration on a multigram scale. Alternatively, water elimination from Henry products followed by a rehydration gives an access to diastereomerically pure glucose-based nitro alcohol which upon reduction provides complementary amino alcohol with gluco-configuration. The latter amino alcohols are transformed into spirooxazolidinones (3-spiropseudonucleosides) via their N-Cbz or N-phenylcarbamate derivatives. The title compounds easily undergo N-derivatization and give highly crystalline materials. Two of the newly obtained (5+5) 3-spiropseudonucleosides are characterized by X-ray crystallography.

α-Chloronitroso compounds derived from carbohydrate ketones: Cycloadditions with cyclic dienes, a synthesis of (-)-physoperuvine and a formal synthesis of (+)-epibatidine

1,2-O-Isopropylidene-α-D-xylofuranose 9 was converted into 5-O-(tert-butyldiphenylsilyl)-3-chloro-3-deoxy-1,2-O-isopropylidene-3-C-nitroso- α-o-xylofuranose 17 in four steps, and a similar α-chloronitroso compound 8 was synthesised from 1,2:5,6-di-O-isopropylidene-α-o-glucofuranose 6, the structures of 8 and 17 being confirmed by X-ray crystallography. Reaction of 8 or 17 with cyclohexa-1,3-diene in the presence of small amounts of water gave the cycloadduct (1S,4R)-3-aza-2-oxabicyclo[2.2.2]oct-5-ene, as its hydrochloride (-)-2, in ≥96% ee. Reactions of either 8 or 17 with cyclohepta-1,3-diene similarly gave (1R,5S)-7-aza-6-oxabicyclo[3.2.2]non-8-ene hydrochloride (-)-25 with ≥96% ee, but reactions with cyclopentadiene proceeded differently, with 17 giving the nitrone (E)-(3 R,5 R)-3-[5′-O-(tert-butyldiphenylsilyl)-3′-deoxy-1′,2′-O-is opropylidene-α-D-erythro-pentofuranos-3′-ylidene-amino]-5-chlorocycl opentene N-oxide 19, the structure of which was determined by X-ray crystallography. The dihydrooxazines (-)-25 and (-)-2 were used in syntheses of (-)-physoperuvine (-)-34 and (+)-epibatidine (+)-40, respectively. A pseudoenantiomeric α-chloronitroso compound 51 was also prepared from 2,3-O-isopropylidene-α-L-sorbofuranose 44, and reaction of 51 with cyclohexa-1,3-diene gave (+)-2 with 97% ee.