α-D-Gulofuranose, 1,2:5,6-bis-O-(1-methylethylidene)-

Basic Information

View in Editor

CAS Number

14686-89-6

Molecular Formula

C12H20O6

Molecular Weight

260.28 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Ethers

Basic Chemical Raw Materials Organic Chemicals Heterocyclic Compounds

Pharmaceutical Chemicals Pharmaceutical Intermediates Heterocyclic Intermediates

Basic Physical Properties

Melting Point

105-106 ºC

SMILES

View in Editor

CC1(OCC(O1)C2C(C3C(O2)OC(O3)(C)C)O)C

InChI

InChI=1S/C12H20O6/c1-11(2)14-5-6(16-11)8-7(13)9-10(15-8)18-12(3,4)17-9/h6-10,13H,5H2,1-4H3/t6-,7-,8+,9-,10-/m1/s1

InChIKey

KEJGAYKWRDILTF-HOTMZDKISA-N

LogP

0.37520

Complexity

342

Synonyms & References

English

14686-89-6
DTXSID301224246
Diacetone-D-glucose
alpha-D-Gulofuranose, 1,2:5,6-bis-O-(1-methylethylidene)-
(3aR,5R,6R,6aR)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,2-d][1,3]dioxol-6-ol
1,2:5,6-Di-O-isopropylidene-
AKOS030241543
1,2:5,6-Di-O-isopropylidene-I+/--D-gulofuranose
DS-3320
CS-B1536
1,2:5,6-Di-O-isopropylidene-a-D-gulofuranose
(3aR,5R,6R,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol
SCHEMBL1847430
1,2:5,6-Di-O-isopropylidene-alpha-D-gulofuranose
(3aR,5R,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
A-D-gulofuranose
1,2:5,6-Bis-O-(1-methylethylidene)-alpha-D-gulofuranose
a-D-Gulofuranose,1,2:5,6-bis-O-(1-methylethylidene)-
1,2:5,6-Di-O-isopropylidene-α-D-gulofuranose
(-)-1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE
1,2,5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE
1,2:5,6-DI-O-ISOPROPYLIDENE-A-D-GULOFURANOSE
Diacetone-D-Glucose
GLUCOFURANOSE
DIACETONE-ALPHA-D-GLC
α-D-Gulose diacetonide
DIACETONE-ALPHA-D-GLUCOSE
DIISOPROPYLIDENEGLUCOFURANOSE
1,2:5,6-Di-O-isopropylidene-α-D-gulose
1,2,5,6-DI-O-ISO-PROPYLIDENEGLUCOFURANOSE
1,2,5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-GULOSE

MDL Number

MFCD00080776

FAQ

What are the physical and chemical properties of α-D-Gulofuranose, 1,2:5,6-bis-O-(1-methylethylidene) (CAS: 14686-89-6)?

α-D-Gulofuranose, 1,2:5,6-bis-O-(1-methylethylidene) (CAS: 14686-89-6) is a cyclic ketose with a molecular weight of approximately 272.3 g/mol. It is a white crystalline solid with a melting point of 179-182 °C. The compound is poorly soluble in water but soluble in ethanol. Chemically, it is highly reactive towards hydrolysis and oxidation.

How is α-D-Gulofuranose, 1,2:5,6-bis-O-(1-methylethylidene) (CAS: 14686-89-6) typically synthesized?

α-D-Gulofuranose, 1,2:5,6-bis-O-(1-methylethylidene) is typically synthesized by the methylation of gulonic acid using a methyl vinyl ketone as the methylation reagent in the presence of a strong acid catalyst, such as sulfuric acid. The process yields a high purity product with good selectivity and yield.

What industries use α-D-Gulofuranose, 1,2:5,6-bis-O-(1-methylethylidene) (CAS: 14686-89-6)?

α-D-Gulofuranose, 1,2:5,6-bis-O-(1-methylethylidene) is primarily used in the pharmaceutical industry for the synthesis of sugar derivatives and in the food industry as a flavoring agent. It also finds applications in the polymer industry for the development of new materials and in the sensors and semiconductors industry for specific chemical sensing applications.

What precautions should be taken when handling α-D-Gulofuranose, 1,2:5,6-bis-O-(1-methylethylidene) (CAS: 14686-89-6)?

When handling α-D-Gulofuranose, 1,2:5,6-bis-O-(1-methylethylidene) (CAS: 14686-89-6), it is essential to use appropriate personal protective equipment (PPE) such as gloves, goggles, and a lab coat. Work should be conducted in a well-ventilated area or a fume hood. Spills should be handled with caution using appropriate absorbents, and the area should be thoroughly cleaned. Always refer to the safety data sheet (SDS) for detailed handling and safety information.