63568-00-3

Basic information

• Product Name: (2Z)-{(4R,5S,6S)-4,5-diacetoxy-6-[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-ylidene}acetonitrile
• Synonyms: (2Z)-{(4R,5S,6S)-4,5-diacetoxy-6-[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-ylidene}acetonitrile
• CAS NO: 63568-00-3
• Molecular Weight: 581.53
• Mol File: 63568-00-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2Z)-{(4R,5S,6S)-4,5-diacetoxy-6-[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-ylidene}acetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (2Z)-{(4R,5S,6S)-4,5-diacetoxy-6-[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-ylidene}acetonitrile(63568-00-3)
• EPA Substance Registry System: (2Z)-{(4R,5S,6S)-4,5-diacetoxy-6-[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-ylidene}acetonitrile(63568-00-3)

Safety Data

• Hazardous Substances Data: 63568-00-3(Hazardous Substances Data)

Upstream product

• 561023-24-3 (2E)-{(4R,5S,6S)-4,5-diacetoxy-6-[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-ylidene}acetonitrile 

Downstream Products

• 63492-69-3 (-)-(2Z)-{(4R,5S,6S)-6-(β-D-glucopyranosyloxy)-4,5-dihydroxycyclohex-2-en-1-ylidene}acetonitrile 

Relevant articles and documents

Total synthesis of (-)-lithospermoside

The total synthesis of the naturally occurring noncyanogenic cyanoglucoside (-)-lithospermoside (1) was achieved starting from optically pure oxatrinorbornenone (+)-2 in 12 steps and 10% overall yield. The key step of the synthesis, the glycosidation, turned out to be very sensitive to steric hindrance, and we had, therefore, to optimize the choice of the protection used for the two other OH functions of the aglycone. Finally, the desired β-D-glucoside 15 was obtained in a very good yield (72%) under Koenigs - Knorr-glycosidation conditions, closely related to those used for the total synthesis of (-)-bauhinin.