(1S,2S,3R,4S,6R)-4,6-Diamino-3-({(2R,3R,6S)-3-amino-6-[(1S)-1-(methylamino)ethyl]tetrahydro-2H-pyran-2-yl}oxy)-2-hydroxycyclohexyl 3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranoside

Basic Information

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CAS Number

1403-66-3

Molecular Formula

C21H43N5O7

Molecular Weight

477.6 g/mol

EINECS

215-765-8

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Ethers

Basic Chemical Raw Materials Organic Chemicals Amines

Basic Chemical Raw Materials Organic Chemicals Heterocyclic Compounds

Pharmaceutical Chemicals Pharmaceutical Intermediates Heterocyclic Intermediates

Polymers and Plastics Thermoplastics Polyolefins

Laboratory Chemicals Research Chemicals Biochemical Reagents

Basic Physical Properties

Melting Point

102-108°

Boiling Point

669.4 °C at 760 mmHg

Density

1.3

Flash Point

358.6 °C

Vapor Pressure

0.0±4.6 mmHg at 25°C

Specific Rotation

D25 +146°

SMILES

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CC([C@@H]1CC[C@H]([C@H](O1)O[C@@H]2[C@H](C[C@H]([C@@H]([C@H]2O)O[C@@H]3[C@@H]([C@H]([C@@](CO3)(C)O)NC)O)N)N)N)NC

InChI

InChI=1S/C21H43N5O7/c1-9(25-3)13-6-5-10(22)19(31-13)32-16-11(23)7-12(24)17(14(16)27)33-20-15(28)18(26-4)21(2,29)8-30-20/h9-20,25-29H,5-8,22-24H2,1-4H3/t9?,10-,11+,12-,13+,14+,15-,16-,17+,18-,19-,20-,21+/m1/s1

InChIKey

CEAZRRDELHUEMR-URQXQFDESA-N

LogP

-3.3274999999999926

pKa

pKa 8.2(66% DMF) (Uncertain);7.9(H2O) (Uncertain)

Topological Polar Surface Area

199.73000000000005 Å²

Hydrogen Bond Donor/Acceptor

11 / 12

Complexity

636

Safety Information

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Hazard Statement

Synonyms & References

English

GENTAMYCINE
GentamysinsolutionforBiochemistry
Gentacycol
GENTAMICIN
GENTAMYCIN
Gentavet
GENTAMICINUM
Refobacin tm
Gentamycin
Uromycine
2-[4,6-Diamino-3-[3-amino-6-(1-methylaminoethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-methylaminooxane-3,5-diol
Lyramycin
Gentamicin
(2R,3R,4S,5R)-2-[(1S,2R,3S,4S,6S)-4,6-Diamino-3-[(2S,3S,6S)-3-amino-6-[(1S)-1-(methylamino)ethyl]oxa

MDL Number

MFCD00072030

EC Number

215-765-8

FAQ

What are the physical and chemical properties of (1S,2S,3R,4S,6R)-4,6-Diamino-3-({(2R,3R,6S)-3-amino-6-[(1S)-1-(methylamino)ethyl]tetrahydro-2H-pyran-2-yl}oxy)-2-hydroxycyclohexyl 3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranoside (CAS: 1403-66-3)?

This compound is a complex organic molecule with a molecular weight of approximately 613.8 g/mol. It is a solid with a crystalline form. The compound exhibits good solubility in organic solvents like dimethylformamide (DMF) and poor solubility in water. Chemically, it shows reactivity towards nucleophiles and electrophiles, making it suitable for various chemical transformations. Its reactivity can be influenced by the presence of amino and hydroxyl groups.

How is (1S,2S,3R,4S,6R)-4,6-Diamino-3-({(2R,3R,6S)-3-amino-6-[(1S)-1-(methylamino)ethyl]tetrahydro-2H-pyran-2-yl}oxy)-2-hydroxycyclohexyl 3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranoside (CAS: 1403-66-3) typically synthesized?

This compound is synthesized through multiple steps, typically involving condensation reactions, amidation, and protection/deprotection steps using appropriate catalysts. The synthesis requires careful control of reaction conditions to achieve high yield and selectivity. Commonly used solvents include dichloromethane (DCM) and acetonitrile, and the reaction is often carried out under anhydrous conditions to prevent side reactions.

What industries use (1S,2S,3R,4S,6R)-4,6-Diamino-3-({(2R,3R,6S)-3-amino-6-[(1S)-1-(methylamino)ethyl]tetrahydro-2H-pyran-2-yl}oxy)-2-hydroxycyclohexyl 3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranoside (CAS: 1403-66-3)?

This compound is primarily used in the pharmaceutical industry for the development of novel drugs and as a building block for complex organic molecules. It may also find applications in the polymer industry for the synthesis of functional polymers and in the sensor industry for developing highly sensitive detection systems. Its unique chemical structure makes it suitable for various biotechnological and chemical applications.

What precautions should be taken when handling (1S,2S,3R,4S,6R)-4,6-Diamino-3-({(2R,3R,6S)-3-amino-6-[(1S)-1-(methylamino)ethyl]tetrahydro-2H-pyran-2-yl}oxy)-2-hydroxycyclohexyl 3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranoside (CAS: 1403-66-3)?

When handling this compound, it is essential to wear appropriate personal protective equipment (PPE) such as gloves, safety glasses, and a lab coat. Work should be conducted in a well-ventilated area or a fume hood to minimize exposure to vapors. Spills should be cleaned up promptly using appropriate absorbent materials. Always consult the Safety Data Sheet (SDS) for specific handling and disposal instructions. The compound should be stored in a cool, dry place away from direct sunlight and heat sources.