2-Carboxy 3-Hydroxy Madol Methyl Ester-d5

Base Information

• Chemical Name: 2-Carboxy 3-Hydroxy Madol Methyl Ester-d5
• CAS No.: 853904-67-3
• Molecular Formula: C₂₂H₃₄O₄
• Molecular Weight: 367.47
• Mol file: 853904-67-3.mol

Synonyms:2-Carboxy 3-Hydroxy Madol Methyl Ester-d5;(5α,17β)-3,17-Dihydroxy-17-(Methyl-d3)-androst-2-ene-16,16-d2-2-carboxylic Acid Methyl Ester-d5

Chemical Property of 2-Carboxy 3-Hydroxy Madol Methyl Ester-d5

Chemical Property:

• PSA: 66.76000
• LogP: 4.37510

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: As Madol (M108000) derivative, 2-Carboxy 3-Hydroxy Madol Methyl Ester-d5 can be used in the preparation of doping agents.

Technology Process of 2-Carboxy 3-Hydroxy Madol Methyl Ester-d5

There total 7 articles about 2-Carboxy 3-Hydroxy Madol Methyl Ester-d5 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: 70.0%

C23H35(2)H5O2Si + methyl cyanoformate (17640-15-2) → 16,16,20,20,20-pentadeuterio-3,17β-dihydroxy-17α-methyl-androst-2-ene-2-carboxylic acid methyl ester (853904-67-3)

Guidance literature:

C₂₃H₃₅⁽²⁾H₅O₂Si; methyl cyanoformate; With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; N-cyclohexylisopropylamine; In tetrahydrofuran; at -80 ℃; for 0.333333h;

With hydrogenchloride; In tetrahydrofuran;

DOI:10.1016/j.steroids.2004.10.002

Reference yield:

16,16,20,20,20-pentadeuterio-17β-hydroxy-17α-methyl-5α-androstan-3-one (853904-66-2) → 16,16,20,20,20-pentadeuterio-3,17β-dihydroxy-17α-methyl-androst-2-ene-2-carboxylic acid methyl ester (853904-67-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 95 percent / imidazole / CH₂Cl₂ / 2 h / 20 °C

2.1: N-isopropylcyclohexylamine; n-BuLi; HMPA / tetrahydrofuran / 0.33 h / -80 °C

2.2: 70 percent / 2n HCl / tetrahydrofuran

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; N-cyclohexylisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.steroids.2004.10.002

Reference yield:

16,16,20,20,20-pentadeuterio-17α-methyl-5α-androstan-3β,17β-diol (853904-65-1) → 16,16,20,20,20-pentadeuterio-3,17β-dihydroxy-17α-methyl-androst-2-ene-2-carboxylic acid methyl ester (853904-67-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 79 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h

2.1: 95 percent / imidazole / CH₂Cl₂ / 2 h / 20 °C

3.1: N-isopropylcyclohexylamine; n-BuLi; HMPA / tetrahydrofuran / 0.33 h / -80 °C

3.2: 70 percent / 2n HCl / tetrahydrofuran

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; N-cyclohexylisopropylamine; Dess-Martin periodane; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.steroids.2004.10.002

upstream raw materials:

methyl cyanoformate

16,16,20,20,20-pentadeuterio-17β-hydroxy-17α-methyl-5α-androstan-3-one

16,16,20,20,20-pentadeuterio-17α-methyl-5α-androstan-3β,17β-diol

16,16-dideuterio-O³-[(1,1-dimethylethyl)dimethylsilanyl] epiandrosterone