155435-45-3

Basic information

• Product Name: 31,42-bis(triethylsilylether)rapamycin
• Synonyms: 31,42-bis(triethylsilylether)rapamycin
• CAS NO: 155435-45-3
• Molecular Weight: 1142.71
• Mol File: 155435-45-3.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 31,42-bis(triethylsilylether)rapamycin(CAS DataBase Reference)
• NIST Chemistry Reference: 31,42-bis(triethylsilylether)rapamycin(155435-45-3)
• EPA Substance Registry System: 31,42-bis(triethylsilylether)rapamycin(155435-45-3)

Safety Data

• Hazardous Substances Data: 155435-45-3(Hazardous Substances Data)

Upstream product

• 331810-13-0 31,42-bis(trimethylsilylether)rapamycin 
• 331810-10-7 31-(trimethylsilylether)rapamycin 
• 79271-56-0 triethylsilyl trifluoromethyl sulfonate 
• 53123-88-9 sirolimus 
• 994-30-9 triethylsilyl chloride 

Downstream Products

• 572924-54-0 Ridaforolimus 
• 159351-69-6 everolimus 
• 179076-05-2 1-hydroxy-19,30-dimethoxy-12-[2-(3-methoxy-4-oxo-cyclohexyl)-1-methyl-ethyl]-15,17,21,23,29,35-hexamethyl-18-triethylsilanyloxy-11,36-dioxa-4-aza-tricyclo[30.3.1.0^4,9]hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentaone 
• 163389-50-2 1,14-dihydroxy-19,30-dimethoxy-12-[2-(3-methoxy-4-triethylsilanyloxy-cyclohexyl)-1-methyl-ethyl]-9,15,17,21,23,29,35-heptamethyl-18-triethylsilanyloxy-11,36-dioxa-4-aza-tricyclo[30.3.1.0^4,9]hexatriaconta-16,24,26,28-tetraene-2,3,10,20-tetraone 
• 160388-98-7 1-hydroxy-12-[2-hydroxy-4-(3-methoxy-4-triethylsilanyloxy-cyclohexyl)-3-methyl-butyl]-17,28-dimethoxy-13,15,19,21,27,33-hexamethyl-16-triethylsilanyloxy-11,34-dioxa-4-aza-tricyclo[28.3.1.0^4,9]tetratriaconta-14,22,24,26-tetraene-2,3,10,18-tetraone 
• 160496-10-6 32(R)-hydroxy-28,40-bis(triethylsilyl)rapamycin 
• 163389-48-8 1-hydroxy-19,30-dimethoxy-12-[2-(3-methoxy-4-triethylsilanyloxy-cyclohexyl)-1-methyl-ethyl]-9,15,17,21,23,29,35-heptamethyl-18-triethylsilanyloxy-11,36-dioxa-4-aza-tricyclo[30.3.1.0^4,9]hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentaone 
• 219725-08-3 28,40-O-bis(triethylsilyl)-21(R),22(R)-dihydroxyrapamycin 
• 219725-06-1 28,40-O-bis(triethylsilyl)-19(R),20(R)-dihydroxyrapamycin 
• 179076-04-1 31-(triethylsilylether)rapamycin 

Relevant articles and documents

Everolimus intermediate, and preparation method and application thereof

The invention discloses an everolimus intermediate, and a preparation method and an application of the everolimus intermediate. A structure of the everolimus intermediate C is shown as formula (1) asshown in the specification. The preparation method comprises the following step: allowing 28-monosilicon protected rapamycin (an everolimus intermediate B) to react with trifluoromethanesulfonic acidsingle-protection glycol ester in the presence of organic base. The invention further discloses the application of the everolimus intermediate C. The preparation method of the everolimus intermediateis simple and high in yield; everolimus prepared from the intermediate can reduce side reactions; a technical operation procedure is simplified; the total yield is increased; the product quality is ensured; and therefore, the preparation method has better industrial application and popularization prospects.

METHOD FOR PREPARING 42-(DIMETHYLPHOSPHINATE) RAPAMYCIN

A method for preparing 42-(dimethylphosphinate) Rapamycin (Ridaforolimus) (I) is provided, which has advantages of high conversion rate and no 31,42-bis(dimethyl phosphinate) Rapamycin (III) generated. In the method of the present invention, Rapamycin (II) is firstly reacted with triethyl chlorosilane in a base condition to form 31,42-bis(triethylsilylether) Rapamycin (IV-b), followed by a selective deprotection process to obtain 31-triethylsilylether Rapamycin (V-b). Next, a phosphorylation reaction is performed by using dimethylphosphinic chloride under a base solution to obtain a crude product. Finally, a deprotection reaction is performed in a diluted sulfuric acid solution to obtain a crude product of Ridaforolimus (I). Since the conversion rate of each step of the method of the present invention is higher than 98%, it indicates that the method of the present invention is suitable for industrial production.

Cleavage of the cyclohexyl-subunit of rapamycin results in loss of immunosuppressive activity

The cyclohexyl-subunit of rapamycin was cleaved by a sequence involving a Baeyer-Villiger reaction and acid hydrolysis of the resulting lactone- acetal as key steps. Binding of this new rapamycin derivative to FKBP12 was only slightly reduced by this modi