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

Basic Information

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CAS Number

7772-79-4

Molecular Formula

C16H23NO10

Molecular Weight

389.36 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

Basic Physical Properties

Melting Point

186-189 ºC

Boiling Point

530.2°C at 760 mmHg

Density

1.3000

Flash Point

274.433°C

Refractive Index

2 ° (C=5, CHCl3)

Specific Rotation

+1.7 to +3.0° (c =4, CHCl3)

SMILES

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CC(=O)NC1C(C(C(OC1OC(=O)C)COC(=O)C)OC(=O)C)OC(=O)C

InChI

InChI=1S/C16H23NO10/c1-7(18)17-13-15(25-10(4)21)14(24-9(3)20)12(6-23-8(2)19)27-16(13)26-11(5)22/h12-16H,6H2,1-5H3,(H,17,18)/t12-,13-,14-,15-,16-/m1/s1

InChIKey

OVPIZHVSWNOZMN-OXGONZEZSA-N

LogP

-0.7943999999999973

Topological Polar Surface Area

143.53000000000003 Å²

Hydrogen Bond Donor/Acceptor

1 / 11

Complexity

604

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

Synonyms & References

English

beta-D-Glucosamine pentaacetate
beta-D-Glucopyranose, 2-(acetylamino)-2-deoxy-, 1,3,4,6-tetraacetate
SCHEMBL404573
7772-79-4
b-D-Glucosamine Pentaacetate
EN300-7375285
CHEMBL567277
DTXSID401167362
2-Acetamido-2-deoxy-beta-D-glucopyranose 1,3,4,6-tetraacetate
Glc-N-Ac free
MFCD00006595
2-ACETAMIDO-1,3,4,6-TETRA-O-ACETYL-2-DEOXY-A-D-GLUCOPYRANOSE
NSC 224432
.beta.-D-Glucosamine Pentaacetate
2-acetamido-2-deoxy-beta-d-glucose tetracetate
2-Acetamido-2-deoxy-beta-D-glucopyranose 1,3,4,6-tetraacetate, 98%
W-201199
(2S,3R,4R,5S,6R)-3-acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate
2-acetamido-2-deoxy-beta-d-glucopyranose-1,3,4,6-tetraacetate
AKOS016009414
OVPIZHVSWNOZMN-OXGONZEZSA-N
2-Acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-beta-D-glucopyranose
2-Acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-alpha-D-glucopyranose
N-Acetyl-beta-D-glucosamine tetraacetate
AS-35041
Pentaacetyl-beta-D-glucosamine
[(2R,3S,4R,5R,6S)-3,4,6-TRIS(ACETYLOXY)-5-ACETAMIDOOXAN-2-YL]METHYL ACETATE
CS-W009736
EINECS 231-865-4
[(2R,3S,4R,5R,6S)-5-acetamido-3,4,6-triacetoxy-tetrahydropyran-2-yl]methyl acetate
D-Glucosamine pentaacetate

MDL Number

MFCD00006595

Customs Code

29329990

FAQ

What are the physical and chemical properties of [(2R,3S,4R,5R,6S)-3,4,6-tris(acetyloxy)-5-acetamidooxan-2-yl]methyl acetate (CAS: 7772-79-4)?

The compound [(2R,3S,4R,5R,6S)-3,4,6-tris(acetyloxy)-5-acetamidooxan-2-yl]methyl acetate is a white crystalline solid with a molecular weight of approximately 540.63 g/mol. It has a very low solubility in water but is soluble in common organic solvents such as ethanol and acetone. The compound is moderately reactive, showing some tendency for hydrolysis and ester interchange under basic conditions. It is stable under neutral and acidic conditions.

How is [(2R,3S,4R,5R,6S)-3,4,6-tris(acetyloxy)-5-acetamidooxan-2-yl]methyl acetate (CAS: 7772-79-4) typically synthesized?

[(2R,3S,4R,5R,6S)-3,4,6-tris(acetyloxy)-5-acetamidooxan-2-yl]methyl acetate is typically synthesized via a multistep process starting from D-(-)-2-hydroxy-3,4,6-tri-O-acetyl-D-glucopyranose. The synthesis involves the protection of the hydroxyl groups with acetyl groups, followed by the introduction of an acetamide group. The reaction is highly selective and yields the compound in good to excellent purity.

What industries use [(2R,3S,4R,5R,6S)-3,4,6-tris(acetyloxy)-5-acetamidooxan-2-yl]methyl acetate (CAS: 7772-79-4)?

This compound is primarily used in the pharmaceutical industry, where it serves as an intermediate in the synthesis of various drugs. It is also utilized in the polymer industry for the modification of polymers and in the sensor industry for the development of new sensor materials. Additionally, it has potential applications in the semiconductor industry due to its structural complexity and reactivity.

What precautions should be taken when handling [(2R,3S,4R,5R,6S)-3,4,6-tris(acetyloxy)-5-acetamidooxan-2-yl]methyl acetate (CAS: 7772-79-4)?

Proper handling of [(2R,3S,4R,5R,6S)-3,4,6-tris(acetyloxy)-5-acetamidooxan-2-yl]methyl acetate requires the use of personal protective equipment (PPE) such as gloves, goggles, and a lab coat. It should be handled in a fume hood to minimize exposure. Spills should be handled with caution, using appropriate absorbent materials, and the area should be flushed with water. The Safety Data Sheet (SDS) should be referenced for detailed emergency procedures and storage conditions.