203120-17-6

Basic information

• Product Name: (4S,5R,6R)-5-Acetamido-4-guanidino-6-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid
• Synonyms: (4S,5R,6R)-5-Acetamido-4-guanidino-6-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid;Laninamivir;(4S,5R,6R)-5-AcetaMido-4-guanidino-6-((1R,2R)-2,3-dihydroxy-1-Methoxypropyl)-5,6-dihydro-4H-pyran-2-;R 125489;Laninamivir (CS-8958);(2R,3R,4S)-3-acetamido-2-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-4-guanidino-3,4-dihydro-2H-pyran-6-carboxylic acid;Laninamivir-d3
• CAS NO: 203120-17-6
• Molecular Formula: C13H22N4O7
• Molecular Weight: 346.34
• Product Categories: Amines;Anti-virals;Carbohydrates & Derivatives;Intermediates & Fine Chemicals;Isotope Labelled Compounds;Pharmaceuticals
• Mol File: 203120-17-6.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Density: 1.61
• Refractive Index: 1.633
• Storage Temp.: -20°C Freezer
• Solubility: Water (Slightly)
• PKA: 3.81±0.70(Predicted)
• CAS DataBase Reference: (4S,5R,6R)-5-Acetamido-4-guanidino-6-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (4S,5R,6R)-5-Acetamido-4-guanidino-6-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid(203120-17-6)
• EPA Substance Registry System: (4S,5R,6R)-5-Acetamido-4-guanidino-6-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid(203120-17-6)

Safety Data

• Hazardous Substances Data: 203120-17-6(Hazardous Substances Data)

Usage

Description

Laninamivir octanoate (CS-8958), an ester prodrug form of the neuraminidase (NA) inhibitor laninamivir (R-125489), was approved in Japan in 2010 for treatment of influenza virus infections. Laninamivir octanoate is given by intranasal administration at a 20 mg or 40 mg dose. It has a long half-life in humans such that efficacy can be achieved after only a single dose. In addition to vaccines for immunoprophylaxis, antiviral drugs play an essential role in the treatment of influenza virus infections. Two viral proteins have been targeted for therapeutic intervention: the M2 ion channel and NA.

Originator

Sankyo Co., Ltd. (Japan)

Uses

Different sources of media describe the Uses of 203120-17-6 differently. You can refer to the following data:
1. A new potent neuraminidase (NA) inhibitor, shows long-acting anti-influenza virus activity.
2. A new potent labelled neuraminidase
3. A new potent neuraminidase

Brand name

Inavir

Synthesis

Laninamivir octanoate is prepared starting from a neuraminic acid precursor. The route from 2,3-didehydroneuramic acid entails a multistep sequence to protect the acid and hydroxyl groups at the 4-, 20-, and 30-positions. Methylation of the remaining 10-hydroxyl by treatment with dimethylsulfate and NaH is followed by conversion of the 4-hydroxyl to an amine Cleavage of the 20,30-dihydroxy protecting group, conversion of the 4- NH2 to the guanidine, and acylation of the 30-OH group afford laninamivir octanoate. This three-step sequence can be reordered such that the guanidine is introduced first, followed by deprotection of the 20,30-diOH groups and acylation. An alternative sequence involves a Boc-protected guanidine intermediate, which is converted in a four-step sequence (deprotection of the acid and 20,30-hydroxyl groups, reprotection of the acid as its diphenylmethyl ether, acylation of the 30-OH and deprotection of the guanidine group) to laninamivir octanoate. Laninamivir can also be synthesized from the a-methyl glycoside of N-acetylneuramic acid methyl ester by an analogous route.

InChI:InChI=1/C13H22N4O7/c1-5(19)16-9-6(17-13(14)15)3-8(12(21)22)24-11(9)10(23-2)7(20)4-18/h3,6-7,9-11,18,20H,4H2,1-2H3,(H,16,19)(H,21,22)(H4,14,15,17)/t6-,7+,9+,10+,11+/m0/s1

Upstream product

• 4023-02-3 1H-pyrazole-1-carboximidamide hydrochloride 
• 1072449-85-4 methyl (3aR,4R,7aR)-4-{(S)-methoxy[(4R)-2-oxo-1,3-dioxolan-4-yl]methyl}-2-methyl-3a,7a-dihydro-4H-pyrano[3,4-d][1,3]oxazole-6-carboxylate 
• 1072449-84-3 methyl (3aS,4R,7aR)-4-{(S)-hydroxy-((4R)-2-oxo-1,3-dioxolan-4-yl)methyl}-2-methyl-3a,7a-dihydro-4H-pyrano[3,4-d][1,3]oxazole-6-carboxylate 
• 475483-21-7 (2R,3R,4S)-3-acetamide-4-amino-2-[(1R,2R)-2,3-dihydroxy-1-methoxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid 
• 1072449-92-3 methyl (4S,5R,6R)-5-acetamido-4-guanidino-6-[(S)-methoxy-((R)-2-oxo-[1,3]dioxolan-4-yl)-methyl]-5,6-dihydro-4H-pyran-2-carboxylate 
• 203120-16-5 (4S,5R,6R,1'S,2'R)-5-acetylamino-4-(bis-N,N'-tert-butyloxycarbonyl)guanidino-6-(2',3'-diacetoxy-1'-methyloxy)propyl-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester 
• 203120-15-4 (4S,5R,6R,1'S,2'R)-5-acetylamino-4-azido-6-(2',3'-diacetoxy-1'-methoxy)propyl-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester 
• 475483-17-1 methyl (4S,5R,6R)-5-acetamido-4-amino-6-[(1S,2R)-2,3-diacetoxy-1-methoxy-propyl]-5,6-dihydro-4H-pyran-2-carboxylate 

Relevant articles and documents

Synthesis and anti-influenza evaluation of polyvalent sialidase inhibitors bearing 4-guanidino-Neu5Ac2en derivatives.

Polyvalent sialidase inhibitors bearing 4-guanidino-Neu5Ac2en derivatives on a poly-L-glutamine backbone are described. Aiming for a longer retention time of 4-guanidino-Neu5Ac2en (zanamivir) in bronchi and lungs, we focused on supermolecules bearing 4-gu

METHOD FOR PRODUCING NEURAMINIC ACID DERIVATIVE

The present invention provides methods for manufacturing neuraminic acid derivatives. [Means for solution] Methods for manufacturing compounds represented by the formula (I) : [wherein R1 represents a C1-C19 alkyl group], or a pharmacologically acceptable salt thereof, using N-acetylneuraminic acid dihydrate as a starting raw material are provided.

METHOD FOR MANUFACTURING NEURAMINIC ACID DERIVATIVES

A method for manufacturing neuraminic acid derivatives is provided, also synthetic intermediates of the neuraminic acid derivatives and methods for their manufacture, and neuraminic acid derivatives having high purity. [Means for solution] A synthetic intermediate compound represented by the formula (7) is provided: [wherein R3 represents alkyl; R4 and R5 each represents H, alkyl, phenyl, or together represent tetramethylene, pentamethylene, oxo].