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(4S,5R,6R)-5-Acetamido-4-guanidino-6-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid

Basic information Safety Supplier Related

(4S,5R,6R)-5-Acetamido-4-guanidino-6-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid 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
  • CS-746
CAS:
203120-17-6
MF:
C13H22N4O7
MW:
346.34
Product Categories:
  • Amines
  • Anti-virals
  • Carbohydrates & Derivatives
  • Intermediates & Fine Chemicals
  • Isotope Labelled Compounds
  • Pharmaceuticals
Mol File:
203120-17-6.mol
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(4S,5R,6R)-5-Acetamido-4-guanidino-6-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid Chemical Properties

Melting point:
>300°C (dec.)
Density 
1.61
storage temp. 
-20°C Freezer
solubility 
Water (Slightly)
pka
3.81±0.70(Predicted)
form 
Solid
color 
White to Off-White
Water Solubility 
Water : 5 mg/mL (14.44 mM; Need ultrasonic)
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(4S,5R,6R)-5-Acetamido-4-guanidino-6-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid Usage And Synthesis

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

A new potent neuraminidase (NA) inhibitor, shows long-acting anti-influenza virus activity.

Uses

A new potent labelled neuraminidase

Definition

ChEBI: Laninamivir is a member of acetamides.

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.

(4S,5R,6R)-5-Acetamido-4-guanidino-6-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acidSupplier

J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Email
jkinfo@jkchemical.com
Adamas Reagent, Ltd.
Tel
400-6009262 16621234537
Email
chenyj@titansci.com
Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Shanghai Fuhe Chemistry Technology Co., Ltd.
Tel
0086-21-67651709
Email
cfx759@hotmail.com
NCE Biomedical Co.,Ltd.
Tel
4000-027-021 |24 +86-13986109188 | +86-15623472865 | +81-08033611988
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(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)Related Product Information