[(2R,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-bromooxan-2-yl]methyl acetate

Basic Information

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CAS Number

572-09-8

Molecular Formula

C14H19BrO9

Molecular Weight

411.2 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Esters

Basic Chemical Raw Materials Organic Chemicals Ethers

Basic Chemical Raw Materials Organic Chemicals Heterocyclic Compounds

Pharmaceutical Chemicals Pharmaceutical Intermediates Heterocyclic Intermediates

Fine Chemicals Surfactants Anionic Surfactants

Laboratory Chemicals Research Chemicals Biochemical Reagents

Basic Physical Properties

Melting Point

87.0 to 92.0 deg-C

Boiling Point

412 oC at 760 mmHg

Density

1.4900

Flash Point

412 oC at 760 mmHg

Refractive Index

1.541

Specific Rotation

194.5 º (c=2,chloroform)

SMILES

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CC(=O)OCC1C(C(C(C(O1)Br)OC(=O)C)OC(=O)C)OC(=O)C

InChI

InChI=1S/C14H19BrO9/c1-6(16)20-5-10-11(21-7(2)17)12(22-8(3)18)13(14(15)24-10)23-9(4)19/h10-14H,5H2,1-4H3/t10-,11-,12+,13-,14+/m1/s1

InChIKey

CYAYKKUWALRRPA-RGDJUOJXSA-N

LogP

0.4643999999999997

Topological Polar Surface Area

114.43 Å²

Hydrogen Bond Donor/Acceptor

0 / 9

Complexity

507

Safety Information

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Hazard Statement

H315 Causes skin irritation
Skin corrosion/irritation

H319 Causes serious eye irritation
Serious eye damage/eye irritation

H335 May cause respiratory irritation
Specific target organ toxicity, single exposure; Respiratory tract irritation

Stability

Stable. Combustible. Incompatible with strong oxidizing agents.

Sensitiveness

Moisture Sensitive

Synonyms & References

English

SCHEMBL989356
2.2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide
2,3,4,6-TETRAACETYL-.ALPHA.-D-GLUCOPYRANOSYL BROMIDE
Acetobromo- alpha -D-glucose
Q27277359
A-D-glucopyranosyl bromide
CYAYKKUWALRRPA-RGDJUOJXSA-N
[(2R,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-bromooxan-2-yl]methyl acetate
NSC-783071
10.14272/CYAYKKUWALRRPA-RGDJUOJXSA-N
ETH4010665
alpha-D-Glucopyranosyl bromide, tetraacetate
acetobromoglucose
2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSYL BROMIDE(STABILIZED WITH 1-2% CACO3)
NS00042860
(2R,3R,4S,5R,6R)-2-(Acetoxymethyl)-6-bromotetrahydro-2H-pyran-3,4,5-triyl triacetate
2,3,4,6-tetra-o-acetyl-alpha-d-glucopyranosyl
T1961
2,3,4,6-Tetra-O-acetylalpha-D-glucopyranosyl bromide
2,3,4,6-tetra-O-Acetyl-
C14H19BrO9
2,3,4,6-O-Tetraacetyl-alpha-D-glucopyranosyl bromide
EN300-69301
A inverted exclamation mark-D-glucopyranosyl
d-acetobromoglucose
ACETOBROMO-.ALPHA.-D-GLUCOSE
Acetobromo-alpha-D-glucose, >=95% (TLC)
2,3,4,6-tetra-O-acetyl-alpha-glucopyranosyl bromide
Acetobromglucose
AS-16072
[(3R,5R,6R)-3,4,5-triacetoxy-6-bromo-tetrahydropyran-2-yl]methyl acetate;2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl Bromide

MDL Number

MFCD00063254

Customs Code

29329985

FAQ

What is [(2R,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-bromooxan-2-yl]methyl acetate (CAS: 572-09-8)?

[(2R,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-bromooxan-2-yl]methyl acetate (CAS: 572-09-8) is a synthetic organic compound characterized by a brominated pentose sugar core with multiple acetyloxy substituents. Its molecular formula is C14H22BrO8, and it exhibits ester functionality, making it a potential intermediate in pharmaceutical and chemical synthesis. The compound is known for its stereochemical complexity and reactivity in functional group transformations.

What are the main uses of [(2R,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-bromooxan-2-yl]methyl acetate (CAS: 572-09-8)?

[(2R,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-bromooxan-2-yl]methyl acetate (CAS: 572-09-8) is primarily used as a synthetic building block in pharmaceutical research, particularly for developing drugs targeting metabolic disorders. It serves as an intermediate in the production of bioactive molecules and is also employed in organic chemistry for studying stereochemistry and acetylation reactions. Its applications extend to chemical manufacturing and research into glycosidic bond modifications.

Is [(2R,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-bromooxan-2-yl]methyl acetate (CAS: 572-09-8) safe?

[(2R,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-bromooxan-2-yl]methyl acetate (CAS: 572-09-8) requires careful handling due to its brominated and ester groups, which may pose moderate toxicity. Safety measures include wearing protective gloves, goggles, and ventilation to prevent skin or respiratory exposure. It is classified as a hazardous chemical under OSHA guidelines, and proper disposal should follow regulatory standards to ensure environmental and occupational safety.

How should [(2R,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-bromooxan-2-yl]methyl acetate (CAS: 572-09-8) be stored?

[(2R,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-bromooxan-2-yl]methyl acetate (CAS: 572-09-8) should be stored in a sealed, airtight container at room temperature (15-25°C) in a cool, dry, and dark location. Maintain low humidity to prevent hydrolysis of the ester groups, and store away from incompatible substances like strong acids or bases. Ensure proper ventilation and label the container clearly for safety.