861668-42-0

Basic information

• Product Name: (-)-(1R,2S,3S,4R)-1,2,3-tris{[(tert-butyl)dimethylsilyl]oxy}-4-phthalimidocyclohex-5-ene
• Synonyms: (-)-(1R,2S,3S,4R)-1,2,3-tris{[(tert-butyl)dimethylsilyl]oxy}-4-phthalimidocyclohex-5-ene
• CAS NO: 861668-42-0
• Molecular Weight: 618.049
• Mol File: 861668-42-0.mol

Chemical Properties

• CAS DataBase Reference: (-)-(1R,2S,3S,4R)-1,2,3-tris{[(tert-butyl)dimethylsilyl]oxy}-4-phthalimidocyclohex-5-ene(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-(1R,2S,3S,4R)-1,2,3-tris{[(tert-butyl)dimethylsilyl]oxy}-4-phthalimidocyclohex-5-ene(861668-42-0)
• EPA Substance Registry System: (-)-(1R,2S,3S,4R)-1,2,3-tris{[(tert-butyl)dimethylsilyl]oxy}-4-phthalimidocyclohex-5-ene(861668-42-0)

Safety Data

• Hazardous Substances Data: 861668-42-0(Hazardous Substances Data)

Upstream product

• 129745-62-6 (-)-(4R,5S,6R)-4,5,6-tris(<(tert-butyl)dimethylsilyl>oxy)cyclohex-2-en-1-one 
• 129745-61-5 (+)-(1R,4R,5S,6S)-5-exo,6-endo-dihydroxy-7-oxabicyclo<2.2.1>heptan-2-one 
• 129829-53-4 (+)-(1R,4R,5R,6R)-2,2-bis(benzyloxy)-5,6-exo-epoxy-7-oxabicyclo<2.2.1>heptane 
• 136918-14-4 phthalimide 

Downstream Products

• 872976-90-4 (-)-(1R,2S,3S,4R)-4-phthalimidocyclohex-5-ene-1,2,3-triol 

Relevant articles and documents

(1S,2S,3R,6R)-6-aminocyclohex-4-ene-1,2,3-triol (=(-)-conduramine B-1) is a selective inhibitor of α-mannosidases. Its inhibitory activity is enhanced by N-benzylation

(-)- and (+)-Conduramine B-1 ((-)- and (+)-5, resp.) have been derived from (+)- and (-)-7-oxabicyclo[2.2.1]hept-5-en-2-one ('naked sugars' of the first generation). Although (-)-5 imitates the structure of β-glucosides, it does not inhibit β-glucosidases

Total asymmetric synthesis of (-)-conduramine B-1 and of its enantiomer. N-Benzyl derivatives of conduramine B-1 are β-glucosidase inhibitors

The 'naked sugars' (+)- and (-)-7-oxabicyclo[2.2.1]hept-5-en-2-one have been converted into (-)-conduramine B-1 ((-)-3) and its enantiomer (+)-3, respectively. They have been condensed with a variety of aldehydes in the presence of NaBH(OAc)3.