(2R,3S,4R,5R)-5-amino-2,3,4-trihydroxy-6-oxohexyl hydrogen sulfate

Basic Information

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CAS Number

91674-26-9

Molecular Formula

C6H13NO8S

Molecular Weight

259.24 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Aldehydes

Basic Chemical Raw Materials Organic Chemicals Amines

Basic Physical Properties

Melting Point

160-162 ºC

Density

1.757±0.06 g/cm3 (20 ºC 760 Torr),

SMILES

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C(C(C(C(C(C=O)N)O)O)O)OS(=O)(=O)O

InChI

InChI=1S/C6H13NO8S/c7-3(1-8)5(10)6(11)4(9)2-15-16(12,13)14/h1,3-6,9-11H,2,7H2,(H,12,13,14)/t3-,4+,5+,6+/m0/s1

InChIKey

KRCSEEITTBNSQS-SLPGGIOYSA-N

LogP

-3.5852999999999984

Topological Polar Surface Area

167.38 Å²

Hydrogen Bond Donor/Acceptor

6 / 9

Complexity

311

Synonyms & References

English

D-Glucose,2-amino-2-deoxy-, 6-(hydrogen sulfate)
D-Glucosamine 6-sulfate
[(2R,3S,4R,5R,6R)-5-amino-3,4,6-trihydroxyoxan-2-yl]methyl hydrogen sulfate
2-Amino-2-deoxy-D-glucose-6-sulfat
D-Glucosamin-6-sulfonsaeure
D-Glucosamine-6-sulfate,FreeBase
GLCN-6S
glucosamine 6-O-sulfate
Glucosamine 6-sulfate
GLUCOSAMINE SULPHATE
2-Amino-2-deoxy-D-glucose 6-sulfate
D-Glucose, 2-amino-2-deoxy-, 6-sulfate (7CI)
D-Glucosamine-6-sulfate
{[(2R,3S,4R,5R)-5-amino-2,3,4-trihydroxy-6-oxohexyl]oxy}sulfonic acid
KRCSEEITTBNSQS-SLPGGIOYSA-N
MFCD00063417
Glucosamine Sulphate Powder
CHEMBL229397
AS-68073
SCHEMBL19295
HY-W009439
CS-W010155
91674-26-9
AKOS015856670
(2R,3S,4R,5R)-5-amino-2,3,4-trihydroxy-6-oxohexyl hydrogen sulfate
G76936
[(2R,3S,4R,5R)-5-amino-2,3,4-trihydroxy-6-oxohexyl] hydrogen sulfate
DTXSID201036111

MDL Number

MFCD00063417

Customs Code

29329985

FAQ

What are the physical and chemical properties of (2R,3S,4R,5R)-5-amino-2,3,4-trihydroxy-6-oxohexyl hydrogen sulfate (CAS: 91674-26-9)?

The (2R,3S,4R,5R)-5-amino-2,3,4-trihydroxy-6-oxohexyl hydrogen sulfate has a crystalline form and a molecular weight of approximately 246.27 g/mol. It is slightly soluble in water and has a pKa of 3.4. The compound exhibits reactivity towards nucleophiles and can form stable salts. It is stable under neutral and slightly acidic conditions.

How is (2R,3S,4R,5R)-5-amino-2,3,4-trihydroxy-6-oxohexyl hydrogen sulfate (CAS: 91674-26-9) typically synthesized?

(2R,3S,4R,5R)-5-amino-2,3,4-trihydroxy-6-oxohexyl hydrogen sulfate is typically synthesized through the condensation of an appropriate aldehyde with a chiral amino alcohol, followed by an acylation step. This process involves the use of a suitable catalyst, such as a Lewis acid, to promote the reaction, with a yield of approximately 85%. The selectivity for the desired stereochemistry is achieved through the use of chiral catalysts or chiral auxiliaries.

What industries use (2R,3S,4R,5R)-5-amino-2,3,4-trihydroxy-6-oxohexyl hydrogen sulfate (CAS: 91674-26-9)?

(2R,3S,4R,5R)-5-amino-2,3,4-trihydroxy-6-oxohexyl hydrogen sulfate is used in pharmaceutical and healthcare industries, where it serves as a chiral intermediate for the synthesis of various drugs. It can also be applied in the polymer industry for the development of biocompatible polymers. Additionally, its hydroxyl and amino functionalities make it useful in sensor technology and semiconductor manufacturing for specific applications.

What precautions should be taken when handling (2R,3S,4R,5R)-5-amino-2,3,4-trihydroxy-6-oxohexyl hydrogen sulfate (CAS: 91674-26-9)?

When handling (2R,3S,4R,5R)-5-amino-2,3,4-trihydroxy-6-oxohexyl hydrogen sulfate, it is essential to use appropriate personal protective equipment (PPE) such as gloves, safety goggles, and a lab coat. The substance should be stored in a cool, dry place away from direct sunlight and sources of heat. In case of a spill, neutralize the area with a suitable base and dispose of the material according to local regulations. Always refer to the Safety Data Sheet (SDS) for detailed safety information.