174531-90-9

Basic information

• Product Name: (2R,4R,7S,8R,9S)-11-<(allyloxycarbonyl)amino>-9-(tert-butyldiphenylsilyloxy)-7,8-epoxy-2,4-dimethyl-1,5-dioxaspiro<5.5>non-10-ene
• Synonyms: (2R,4R,7S,8R,9S)-11-<(allyloxycarbonyl)amino>-9-(tert-butyldiphenylsilyloxy)-7,8-epoxy-2,4-dimethyl-1,5-dioxaspiro<5.5>non-10-ene
• CAS NO: 174531-90-9
• Molecular Weight: 549.739
• Mol File: 174531-90-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,4R,7S,8R,9S)-11-<(allyloxycarbonyl)amino>-9-(tert-butyldiphenylsilyloxy)-7,8-epoxy-2,4-dimethyl-1,5-dioxaspiro<5.5>non-10-ene(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,4R,7S,8R,9S)-11-<(allyloxycarbonyl)amino>-9-(tert-butyldiphenylsilyloxy)-7,8-epoxy-2,4-dimethyl-1,5-dioxaspiro<5.5>non-10-ene(174531-90-9)
• EPA Substance Registry System: (2R,4R,7S,8R,9S)-11-<(allyloxycarbonyl)amino>-9-(tert-butyldiphenylsilyloxy)-7,8-epoxy-2,4-dimethyl-1,5-dioxaspiro<5.5>non-10-ene(174531-90-9)

Safety Data

• Hazardous Substances Data: 174531-90-9(Hazardous Substances Data)

Upstream product

• 174531-87-4 (2R,4R)-7-<(allyloxycarbonyl)amino>-2,4-dimethyl-1,5-dioxaspiro<5.5>nona-7,10-dien-9-one 
• 42075-32-1 (2R,4R)-pentanediol 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 174531-88-5 (2R,4R,7S,8R)-11-<(allyloxycarbonyl)amino>-7,8-epoxy-2,4-dimethyl-1,5-dioxaspiro<5.5>non-10-en-9-one 

Downstream Products

• 174591-71-0 (2S,3R,4S)-6--4-(tert-butyldiphenylsilyloxy)-2,3-epoxycyclohex-5-enone 
• 174591-72-1 (2S,3R,4S)-6-acetamido-4-(tert-butyldiphenylsilyloxy)-2,3-epoxycyclohex-5-enone 
• 93752-54-6 LL-C10037α 
• 174591-70-9 (2S,3R,4S)-6-<(allyloxycarbonyl)amino>-4-(tert-butyldiphenylsilyloxy)-2,3-epoxycyclohex-5-enone 

Relevant articles and documents

Synthesis of (-)-LL-C10037α and related manumycin-type epoxyquinols

Starting with N-allyloxycarbonyl-protected 2,5-dimethoxyaniline, hypervalent iodine oxidation protocols and selective enone epoxidation provides the Streptomyces metabolite LL-C10037α in nine steps and 7-10% overall yield. In an asymmetric variant of this strategy, (R,R)-pentane-2,4-diol is used as a chiral acetalization agent. The resulting semiquinone spiroacetal, due to an ortho-acylamino substituent that restricts the 1,3-dioxane ring conformation, undergoes face-selective epoxidation and is further functionalized to give (-)-LL-C10037α in 94% ee. These pathways represent the first syntheses of the highly functionalized mC7N core of the manumycins and have been further extended toward the preparation of analogs for SAR studies of this class of antitumor antibiotics. Manumycins inhibit the farnesylation of Ras-protein by PFTase (protein farnesyltransferase).