197250-11-6

Basic information

• Product Name: C₆₆H₁₀₁NO₁₂Si₂
• Synonyms: C₆₆H₁₀₁NO₁₂Si₂
• CAS NO: 197250-11-6
• Molecular Weight: 1156.7
• Mol File: 197250-11-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: C₆₆H₁₀₁NO₁₂Si₂(CAS DataBase Reference)
• NIST Chemistry Reference: C₆₆H₁₀₁NO₁₂Si₂(197250-11-6)
• EPA Substance Registry System: C₆₆H₁₀₁NO₁₂Si₂(197250-11-6)

Safety Data

• Hazardous Substances Data: 197250-11-6(Hazardous Substances Data)

Upstream product

• 197250-10-5 C₆₉H₁₀₇NO₁₂Si₂ 

Downstream Products

• 104987-11-3 Tacrolimus 

Relevant articles and documents

Total synthesis of FK-506. Part 2: Completion of the synthesis

The C15-C16 bond of FK-506 was formed via sulfone anion coupling followed by chelation controlled reduction of the C15 ketone. Efficient methylation of the C15-OH was accomplished by a combination of Me3OBF4-4A molecular sieves in the presence of Proton Sponge. A procedure was developed to avoid epimerization at the C2 position of the pipecolinate section during alkaline hydrolysis. A reductive fragmentation of the C21-C24 [6,6]-spiroketal iodide using active Zn/Aggraphite delivered the α'-allyl aldol section. The C9-C10 [5,6]-spiroketal acetonide was de-blocked via a novel β-elimination, using a combination of LiHMDS-Mg(HMDS)2 in HMPA-DME (I:]), to afford an enediol acetal, which was oxidized with dimethyl dioxirane to generate the C8-C10 a, P diketoanlide acetal function. Final desilylations completed the total synthesis of FK-506.