(6R)-5-Acetamido-2,6-anhydro-4-carbamimidamido-3,4,5-trideoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]-L-threo-hex-2-enonic acid

Basic Information

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CAS Number

139110-80-8

Molecular Formula

C12H20N4O7

Molecular Weight

332.31 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

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

Fine Chemicals Surfactants Anionic Surfactants

Basic Physical Properties

Melting Point

274-277°C

Solubility

H2O: soluble10mg/mL, clear

Specific Rotation

+33° - +42° (c=0.9, H2O)

SMILES

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CC(=O)N[C@@H]1[C@H](C=C(O[C@H]1[C@@H]([C@@H](CO)O)O)C(=O)O)NC(=N)N

InChI

InChI=1S/C12H20N4O7/c1-4(18)15-8-5(16-12(13)14)2-7(11(21)22)23-10(8)9(20)6(19)3-17/h2,5-6,8-10,17,19-20H,3H2,1H3,(H,15,18)(H,21,22)(H4,13,14,16)/t5-,6+,8+,9+,10+/m0/s1

InChIKey

ARAIBEBZBOPLMB-UFGQHTETSA-N

LogP

-3.5758299999999963

Topological Polar Surface Area

198.22 Å²

Hydrogen Bond Donor/Acceptor

9 / 11

Complexity

518

Safety Information

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Hazard Statement

H302 Harmful if swallowed
Acute toxicity, oral

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

ZANAMIVIR HYDRATE
4-Guanidino-2,4-dideoxy-2,3-dehydro-N-acetylneuraminic acid
4-Guanidino-Neu5Ac2en
D-glycero-D-galacto-Non-2-enonic acid, 5-(acetylamino)-4-[(aminoiminomethyl)amino]-2,6-anhydro-3,4,5-trideoxy- (9CI)
GANA
GANA (inhibitor)
GG 167
ZanaMivir
4-Guanidino-2,4-dideoxy-2,3-dehydro-N-acetylneuraminic acid 4-Guanidino-Neu5Ac2en
5-acetamido-4-guanidino-2,3,4,5-tetradeoxy-D-glycero-D-galacto-non-2-enopyranosonic acid
Relenza
Unii-L6o3xi777i
Zanamir
(2R,3R,4S)-3-Acetamido-4-(diaminomethylideneamino)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
Zanamavir
MODIFIED SIALIC ACID
GG167
Zanamivir (Relenza)
Relenza (TN)
GR 121167X
L6O3XI777I
ZMR
5-Acetamido-2,6-anhydro-3,4,5-trideoxy-4-guanidino-D-glycero-D-galacto-non-2-enonic acid
GNA
DSSTox_CID_3749
DSSTox_RID_77184
DSSTox_GSID_23749
Zanamivir [USAN:INN:BAN]
HSDB
Zanamivir

MDL Number

MFCD03791324

FAQ

What are the physical and chemical properties of (6R)-5-Acetamido-2,6-anhydro-4-carbamimidamido-3,4,5-trideoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]-L-threo-hex-2-enonic acid (CAS: 139110-80-8)?

(6R)-5-Acetamido-2,6-anhydro-4-carbamimidamido-3,4,5-trideoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]-L-threo-hex-2-enonic acid is a crystalline compound with a molecular weight of approximately 456.45 g/mol. It has good solubility in water and is slightly soluble in ethanol. This compound is highly reactive and susceptible to hydrolysis. It is also prone to degradation under acidic or basic conditions.

How is (6R)-5-Acetamido-2,6-anhydro-4-carbamimidamido-3,4,5-trideoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]-L-threo-hex-2-enonic acid (CAS: 139110-80-8) typically synthesized?

(6R)-5-Acetamido-2,6-anhydro-4-carbamimidamido-3,4,5-trideoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]-L-threo-hex-2-enonic acid is usually synthesized through multi-step organic synthesis involving acylation, amide formation, and carbamate protection. Commonly used catalysts include acid or base catalysts, and the reaction yield is typically high. Optimal conditions for selectivity and purity are crucial for successful synthesis.

What industries use (6R)-5-Acetamido-2,6-anhydro-4-carbamimidamido-3,4,5-trideoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]-L-threo-hex-2-enonic acid (CAS: 139110-80-8)?

(6R)-5-Acetamido-2,6-anhydro-4-carbamimidamido-3,4,5-trideoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]-L-threo-hex-2-enonic acid is primarily used in the pharmaceutical industry for the development of new drugs. It also finds applications in polymer science, where it can be used as a monomer, and in sensor technology for its unique chemical properties. Additionally, it is of interest in semiconductor manufacturing due to its potential use in material science.

What precautions should be taken when handling (6R)-5-Acetamido-2,6-anhydro-4-carbamimidamido-3,4,5-trideoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]-L-threo-hex-2-enonic acid (CAS: 139110-80-8)?

When handling (6R)-5-Acetamido-2,6-anhydro-4-carbamimidamido-3,4,5-trideoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]-L-threo-hex-2-enonic acid, it is essential to wear 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 to minimize inhalation risks. Spills should be cleaned up using appropriate absorbents and disposed of according to local regulations. Always consult the safety data sheet (SDS) for specific handling guidelines and emergency procedures.