Kifunensine

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Names

[ CAS No. ]:
109944-15-2

[ Name ]:
Kifunensine

[Synonym ]:
(5R,6R,7S,8R,8aS)-6,7,8-Trihydroxy-5-(hydroxymethyl)hexahydroimidazo[1,2-a]pyridine-2,3-dione
Imidazo[1,2-a]pyridine-2,3-dione, hexahydro-6,7,8-trihydroxy-5-(hydroxymethyl)-, (5R,6R,7S,8R,8aS)-
KIFUNENSINE,KITASATOSPORIA KIFUNENSE
1-deoxymannojirimycin
Kifunensine

Chemical & Physical Properties

[ Density]:
1.9±0.1 g/cm3

[ Melting Point ]:
>280℃

[ Molecular Formula ]:
C8H12N2O6

[ Molecular Weight ]:
232.191

[ Exact Mass ]:
232.069534

[ PSA ]:
130.33000

[ LogP ]:
-2.21

[ Index of Refraction ]:
1.706

[ Storage condition ]:
-20°C

MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Precursor & DownStream

Precursor

  • Kifunensine diacetonide
  • 2-Deoxy-1,3:4,5-di-O-isopropylidene-2-oxamoylamino-D-mannitol
  • 5-Deoxy-2,3:4,6-di-O-isopropylidene-5-oxamoylamino-D-mannose
  • (2R,3R,4R,5R)-5-amino-2,3:4,6-di(isopropylidenedioxy)hexanol
  • ((4R,5S)-5-((1R,2R)-2-azido-1,3-dihydroxypropyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl pivalate
  • (2R,3R,4R,5R)-2-azido-1,3:4,5-di(isopropylidenedioxy)-6-pivaloyloxyhexane
  • (2R,3R,4R,5R)-5-azido-6-tert-butyldimethylsilanyloxy-2,3-isopropylidenedioxy-1,4-hexanediol
  • (2R,3R,4R,5R)-2-azido-1-tert-butyldimethylsilanyloxy-4,5-isopropylidenedioxy-6-pivaloyloxy-3-hexanol
  • 6-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-L-gulonolactone
  • 5-Azido-6-(tert-butyldimethylsilyl)-2,3-O-isopropylidene L-Gulono-1,4-lactone

DownStream

  • Kifunensine diacetonide

Articles

A context-independent N-glycan signal targets the misfolded extracellular domain of Arabidopsis STRUBBELIG to endoplasmic-reticulum-associated degradation.

Biochem. J. 464(3) , 401-11, (2014)

N-glycosylation of proteins plays an important role in the determination of the fate of newly synthesized glycoproteins in the endoplasmic reticulum (ER). Specific oligosaccharide structures recruit m...

Synthesis of kifunensine thioanalogs and their inhibitory activities against HIV-RT and α-mannosidase.

Carbohydr. Res. 365 , 1-8, (2013)

An efficient and practical synthesis of kifunensine thioanalogs 1a-c was reported. The bicyclic azasugars fused thiazolidin-4-one 4a-c as key intermediates were first synthesized in good yields of 74-...

Evolution of cross-neutralizing antibody specificities to the CD4-BS and the carbohydrate cloak of the HIV Env in an HIV-1-infected subject.

PLoS ONE 7(11) , e49610, (2012)

Broadly neutralizing antibodies are considered an important part of a successful HIV vaccine. A better understanding of the factors underlying their development during infection and of the epitopes th...


More Articles


Related Compounds

  • Kifunensine
  • Kifunensine diacetonide
  • Ethyl (2-Methyl-propane-1-sulfonyl)-acetate
  • 4-Fluoro-2-[(4-methyl-1-piperazinyl)methyl]aniline
  • 4-(5-Fluoro-2-nitrophenyl)butan-2-amine
  • 6-(3-Chloro-2-fluorophenyl)-4-pyrimidinecarboxylic acid
  • 6-(3-Chlorophenyl)-2-methylpyrimidine-4-carboxylic acid
  • Methyl 6-(3-methylphenyl)pyrimidine-4-carboxylate
  • 6-(3-Methoxyphenyl)pyrimidine-4-carboxylic acid
  • 6-(3-Methylphenyl)pyrimidine-4-carboxylic acid
  • 1-Methylindolin-5-amine hydrochloride
  • 1-(3-Benzyl-1,2,4-oxadiazol-5-yl)-3-(methylsulfanyl)propan-1-amine
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