162635-03-2

Basic information

• Product Name: Temsirolimus Acetonide
• Synonyms: Rapamycin 42-(2,2,5-Trimethyl-1,3-dioxane-5-carboxylate);Temsirolimus Acetonide
• CAS NO: 162635-03-2
• Molecular Formula: C₅₉H₉₁NO₁₆
• Molecular Weight: 1070.36
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 162635-03-2.mol
• Article Data: 8

Chemical Properties

• Melting Point: 89-91°C
• Appearance: /
• Refractive Index: 1.547
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility: Chloroform, Methanol
• CAS DataBase Reference: Temsirolimus Acetonide(CAS DataBase Reference)
• NIST Chemistry Reference: Temsirolimus Acetonide(162635-03-2)
• EPA Substance Registry System: Temsirolimus Acetonide(162635-03-2)

Safety Data

• Hazardous Substances Data: 162635-03-2(Hazardous Substances Data)

Usage

Chemical Properties

White Gel

Uses

Different sources of media describe the Uses of 162635-03-2 differently. You can refer to the following data:
1. Rapamycin 42-ester derivative
2. Rapamycin 42-ester derivative.

InChI:InChI=1/C59H91NO16/c1-35-19-15-14-16-20-36(2)47(69-11)31-43-24-22-41(7)59(68,76-43)53(64)54(65)60-26-18-17-21-44(60)55(66)74-48(32-45(61)37(3)28-40(6)51(63)52(71-13)50(62)39(5)27-35)38(4)29-42-23-25-46(49(30-42)70-12)75-56(67)58(10)33-72-57(8,9)73-34-58/h14-16,19-20,28,35,37-39,41-44,46-49,51-52,63,68H,17-18,21-27,29-34H2,1-13H3/b16-14+,19-15+,36-20+,40-28+/t35-,37-,38-,39-,41-,42+,43+,44+,46-,47+,48+,49-,51-,52+,59-/m1/s1

Upstream product

• 16837-14-2 2,2,5-trimethyl-1,3-dioxane-5-carboxylic acid 
• 53123-88-9 sirolimus 
• 162635-10-1 2,4,6-trichlorobenzoic-2',2',5'-trimethyl-1',3'-dioxane-5'-carboxylic anhydride 
• 4767-03-7 2,2-bis(hydroxymethyl)propionic acid 
• 408322-03-2 2,2,5-trimethyl-1,3-dioxane-5-carboxylic anhydride 
• 331810-11-8 2,2,5-trimethyl-1,3-dioxane-5-carboxylic acid chloride 
• 865860-80-6 2,2,5-trimethyl-[1,3]dioxane-5-carboxylic acid vinyl ester 

Downstream Products

• 162635-04-3 temsirolimus 

Relevant articles and documents

Method for separating and purifying temsirolimus

The invention discloses a method for separating and purifying temsirolimus. The method comprises the following steps: (1) synthesis of a crude product; and (2) separation and purification. The specific separation and purification method has the advantages of great improvement of the purity and the yield of temsirolimus, reduction of the cost, and broad market application prospect.

Preparation method for temsirolimus

The invention provides a preparation method for temsirolimus. The preparation method comprises the following steps: step 1, dissolving 2,2,5-trimethyl-1,3-dioxane-5-carboxylic acid in a solvent underan alkaline condition, dropwise adding a solution of 2,4,6-trichlorobenzoyl chloride under stirring at a normal temperature, after a reaction is completed, carrying out cooling, adding a rapamycin double-protection compound, then dropwise adding an alkaline solution, and carrying out a reaction so as to obtain a coupled intermediate; and step 2, dissolving the coupled intermediate into a solvent,carrying out cooling, dropwise adding an inorganic acid solution, and carrying out deprotection so as to obtain the temsirolimus. The preparation method provided by the invention has the advantages ofsimple process, easy operation, high reaction yield, few by-products and applicability to industrial production.

REGIOSELECTIVE ACYLATION OF RAPAMYCIN AT THE C-42 POSITION

The invention refers to the selective acylation of Rapamycin at the 42-position (I) with an acylating agent of the formula (II) wherein R4 and R5 are the same or different, individually the rest of an acetal, especially tetrahydropyran, or of a carbonate or the rest of a silyl ether or taken together are the rest of a boronate, an acetal or ketal.