Everolimus Related Compound 3

Base Information

• Chemical Name: Everolimus Related Compound 3
• CAS No.: 147438-30-0
• Molecular Formula: C₃₂H₄₉NO₉
• Molecular Weight: 591.742
• Mol file: 147438-30-0.mol

Synonyms:(S)-1-{2-[(2R,3R,6S)-6-((3E,5E,7E)-(2S,9S,11R)-2,13-Dimethoxy-3,9,11-trimethyl-12-oxo-trideca-3,5,7-trienyl)-2-hydroxy-3-methyl-tetrahydro-pyran-2-yl]-2-oxo-acetyl}-piperidine-2-carboxylic acid

Chemical Property of Everolimus Related Compound 3

Chemical Property:

• Boiling Point: 734.4±70.0 °C(Predicted)
• PKA: 3.24±0.20(Predicted)
• Density: 1.144±0.06 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

(2S)?-1-?[2-?[(2R,?3R,?6S)?-?6-?[(2S,?3E,?5E,?7E,?9S,?11R)?-?2,?13-?Dimethoxy-?3,?9,?11-?trimethyl-?12-?oxo-?3,?5,?7-?tridecatrien-?1-?yl]?tetrahydro-?2-?hydroxy-?3-?methyl-?2H-?pyran-?2-?yl]?-?2-?oxoacetyl]?-?2-?piperidinecarboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (2S)?-1-?[2-?[(2R,?3R,?6S)?-?6-?[(2S,?3E,?5E,?7E,?9S,?11R)?-?2,?13-?Dimethoxy-?3,?9,?11-?trimethyl-?12-?oxo-?3,?5,?7-?tridecatrien-?1-?yl]?tetrahydro-?2-?hydroxy-?3-?methyl-?2H-?pyran-?2-?yl]?-?2-?oxoacetyl]?-?2-?piperidinecarboxylic Acid is an impurity of Sirolimus (R124000) which is an immunosuppressant drug used to prevent rejection in organ transplantation.

Technology Process of Everolimus Related Compound 3

There total 9 articles about Everolimus Related Compound 3 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.0%

28-secorapamycin (147438-29-7) → (S)-1-{2-[(2R,3R,6S)-6-((3E,5E,7E)-(2S,9S,11R)-2,13-Dimethoxy-3,9,11-trimethyl-12-oxo-trideca-3,5,7-trienyl)-2-hydroxy-3-methyl-tetrahydro-pyran-2-yl]-2-oxo-acetyl}-piperidine-2-carboxylic acid (147438-30-0) + (2E,6E)-(4R,8R)-9-((1S,3R,4R)-4-Hydroxy-3-methoxy-cyclohexyl)-2,4,8-trimethyl-5-oxo-nona-2,6-dienal (146404-45-7)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1016/S0040-4039(00)77473-9

Reference yield:

(S)-1-{2-[(2R,3R,6S)-6-((3E,5E,7E)-(2S,9S,11R)-2,13-Dimethoxy-3,9,11-trimethyl-12-oxo-trideca-3,5,7-trienyl)-2-hydroxy-3-methyl-tetrahydro-pyran-2-yl]-2-oxo-acetyl}-piperidine-2-carboxylic acid tert-butyl ester (151058-33-2) → (S)-1-{2-[(2R,3R,6S)-6-((3E,5E,7E)-(2S,9S,11R)-2,13-Dimethoxy-3,9,11-trimethyl-12-oxo-trideca-3,5,7-trienyl)-2-hydroxy-3-methyl-tetrahydro-pyran-2-yl]-2-oxo-acetyl}-piperidine-2-carboxylic acid (147438-30-0)

Guidance literature:

With formic acid; In dichloromethane; at 25 ℃;

DOI:10.1021/ja00073a083

Reference yield:

(8E,10E,12E)-(2R,5S,7S,14S,16R)-5-(tert-Butyl-dimethyl-silanyloxy)-7,18-dimethoxy-2,8,14,16-tetramethyl-17-oxo-octadeca-8,10,12-trienal (146404-48-0) → (S)-1-{2-[(2R,3R,6S)-6-((3E,5E,7E)-(2S,9S,11R)-2,13-Dimethoxy-3,9,11-trimethyl-12-oxo-trideca-3,5,7-trienyl)-2-hydroxy-3-methyl-tetrahydro-pyran-2-yl]-2-oxo-acetyl}-piperidine-2-carboxylic acid (147438-30-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) LDA / 1.) THF, -78 deg C

2: Dess-Martin periodinate, pyridine / CH₂Cl₂ / 25 °C

3: HF*pyridine / tetrahydrofuran / 25 °C

4: HCO₂H / CH₂Cl₂ / 25 °C

With pyridine; formic acid; Dess-Martin periodane; pyridine hydrogenfluoride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00073a083

upstream raw materials:

28-secorapamycin

sirolimus

(S)-1-{2-[(2R,3R,6S)-6-((3E,5E,7E)-(2S,9S,11R)-2,13-Dimethoxy-3,9,11-trimethyl-12-oxo-trideca-3,5,7-trienyl)-2-hydroxy-3-methyl-tetrahydro-pyran-2-yl]-2-oxo-acetyl}-piperidine-2-carboxylic acid tert-butyl ester

(8E,10E,12E)-(2R,5S,7S,14S,16R)-5-(tert-Butyl-dimethyl-silanyloxy)-7,18-dimethoxy-2,8,14,16-tetramethyl-17-oxo-octadeca-8,10,12-trienal

Refernces

• 1、 Yohannes,Myers,Danishefsky. "Degradation of rapamycin: Synthesis of a rapamycin derived fragment containing the tricarbonyl and triene sectors". . p. 2075 - 2078. Retrieved 2007/10/02.