159351-68-5

Basic information

• Product Name: 40-O-[2-(t-butyldimethylsilyl)oxy]ethyl rapamycin
• Synonyms: 40-O-[2-(t-butyldimethylsilyl)oxy]ethyl rapamycin
• CAS NO: 159351-68-5
• Molecular Weight: 1072.5
• Mol File: 159351-68-5.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 997.3±75.0 °C(Predicted)
• Density: 1.12±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 40-O-[2-(t-butyldimethylsilyl)oxy]ethyl rapamycin(CAS DataBase Reference)
• NIST Chemistry Reference: 40-O-[2-(t-butyldimethylsilyl)oxy]ethyl rapamycin(159351-68-5)
• EPA Substance Registry System: 40-O-[2-(t-butyldimethylsilyl)oxy]ethyl rapamycin(159351-68-5)

Safety Data

• Hazardous Substances Data: 159351-68-5(Hazardous Substances Data)

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 102229-10-7 2-(tert-butyldimethylsilyloxy)ethanol 
• 53123-88-9 sirolimus 
• 159351-69-6 everolimus 
• 75-21-8 oxirane 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 164162-36-1 2-(t-Butyldimethylsilyloxy)ethyl trifluoromethanesulfonate 

Downstream Products

• 159351-69-6 everolimus 

Relevant articles and documents

Purification method of everolimus

The invention provides a purification method of everolimus. According to the method, derivatization, separation and hydrolysis are carried out on everolimus, the treated everolimus has greatly reducedimpurity rapamycin content, and further by means of one-time preparation of liquid phase for purification, a high purity product with high yield can be obtained, thereby reducing the industrial costof the purification steps. The invention also further provides a preparation method of everolimus. The method has the advantages of high yield and simple operation, and is suitable for industrial production.

Preparation method of everolimus

The invention discloses a preparation method of everolimus. The preparation method comprises the following step of performing deprotection reaction on an everolimus intermediate C. The preparation method of everolimus adopts a manner of regioselective protection of rapamycin 28-hydroxyl, so that the selectivity of a 40-hydroxyl alkylation reaction is improved; side reactions are reduced; a total yield of everolimus calculated from rapamycin can reach above 70%; compared with yields reported in available literatures, the yield is greatly increased; a technical operation procedure is simplified;the product quality is ensured; and the preparation method has better industrial application and popularization prospects.

METHOD FOR THE SYNTHESIS OF RAPAMYCIN DERIVATIVES

The present invention relates to a method for the production of a rapamycin derivative of formula (I), the method comprising the preparation of a 2-(tri-substituted silyl)oxyethyl triflate by reacting ethylene oxide and a tri-substituted silyl triflate, reaction of the resulting 2-(tri-substituted silyl)oxyethyl triflate with rapamycin in the presence of a molar excess of organic base, and deprotection to obtain the rapamycin derivative of compound (I).