(21S)-3-O-benzyl-21-methyldigitoxigenin

Base Information

• Chemical Name: (21S)-3-O-benzyl-21-methyldigitoxigenin
• CAS No.: 92588-18-6
• Molecular Formula: C₃₁H₄₂O₄
• Molecular Weight: 478.672
• Mol file: 92588-18-6.mol

Synonyms:

Chemical Property of (21S)-3-O-benzyl-21-methyldigitoxigenin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (21S)-3-O-benzyl-21-methyldigitoxigenin

There total 8 articles about (21S)-3-O-benzyl-21-methyldigitoxigenin 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:

3β-benzyloxy-5β-androst-15-en-17-one (73336-58-0) → (21S)-3-O-benzyl-21-methyldigitoxigenin (92588-18-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) BuLi / 1.) Et₂O, hexane, -70 deg, 1 h; 2.) Et₂O, 1 h

2: 4-dimethylaminopyridine / pyridine / 24 h / Ambient temperature

3: 3 g / H₂O, CaCO₃ / acetone / 15 h / Heating

4: 90 percent / H₂, AcONa / 10percent Pd/CaCO₃ / ethanol; H₂O / Ambient temperature

5: m-chloroperbenzoic acid, AcONa, AcOH, / CHCl₃ / 2 h / Ambient temperature

6: 1.3 g / NaBH₄ / CH₂Cl₂; H₂O / 8 h / Ambient temperature

7: 91 percent / SOCl₂ / CH₂Cl₂; pyridine / -78 deg C to 0 deg C; 0 deg C, 1/2 h

8: 1.) AcOH, H₂O, N-bromoacetamide; 2.) AcONa / 2.) Raney-Ni / 1.) acetone, 5-10 deg C, 1/2 h; 2.) CH₂Cl₂/MeOH, ice bath then rt., 1 h

With dmap; sodium tetrahydroborate; n-butyllithium; thionyl chloride; water; hydrogen; sodium acetate; acetic acid; 3-chloro-benzenecarboperoxoic acid; calcium carbonate; N-bromoacetamide; Lindlar's catalyst; nickel; In pyridine; ethanol; dichloromethane; chloroform; water; acetone;

DOI:10.1002/hlca.19840670427

Reference yield:

2-methyl-3-(3'β-benzyloxy-15'β-hydroxy-5'β-androstan-17'β-yl)furan (92588-13-1) → (21S)-3-O-benzyl-21-methyldigitoxigenin (92588-18-6)

Guidance literature:

Multi-step reaction with 4 steps

1: m-chloroperbenzoic acid, AcONa, AcOH, / CHCl₃ / 2 h / Ambient temperature

2: 1.3 g / NaBH₄ / CH₂Cl₂; H₂O / 8 h / Ambient temperature

3: 91 percent / SOCl₂ / CH₂Cl₂; pyridine / -78 deg C to 0 deg C; 0 deg C, 1/2 h

4: 1.) AcOH, H₂O, N-bromoacetamide; 2.) AcONa / 2.) Raney-Ni / 1.) acetone, 5-10 deg C, 1/2 h; 2.) CH₂Cl₂/MeOH, ice bath then rt., 1 h

With sodium tetrahydroborate; thionyl chloride; water; sodium acetate; acetic acid; 3-chloro-benzenecarboperoxoic acid; N-bromoacetamide; nickel; In pyridine; dichloromethane; chloroform; water;

DOI:10.1002/hlca.19840670427

Reference yield:

2-methyl-3-(3'β-benzyloxy-17'β-hydroxy-5'β-androst-15'-en-17'α-yl)furan (83457-07-2) → (21S)-3-O-benzyl-21-methyldigitoxigenin (92588-18-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 4-dimethylaminopyridine / pyridine / 24 h / Ambient temperature

2: 3 g / H₂O, CaCO₃ / acetone / 15 h / Heating

3: 90 percent / H₂, AcONa / 10percent Pd/CaCO₃ / ethanol; H₂O / Ambient temperature

4: m-chloroperbenzoic acid, AcONa, AcOH, / CHCl₃ / 2 h / Ambient temperature

5: 1.3 g / NaBH₄ / CH₂Cl₂; H₂O / 8 h / Ambient temperature

6: 91 percent / SOCl₂ / CH₂Cl₂; pyridine / -78 deg C to 0 deg C; 0 deg C, 1/2 h

7: 1.) AcOH, H₂O, N-bromoacetamide; 2.) AcONa / 2.) Raney-Ni / 1.) acetone, 5-10 deg C, 1/2 h; 2.) CH₂Cl₂/MeOH, ice bath then rt., 1 h

With dmap; sodium tetrahydroborate; thionyl chloride; water; hydrogen; sodium acetate; acetic acid; 3-chloro-benzenecarboperoxoic acid; calcium carbonate; N-bromoacetamide; Lindlar's catalyst; nickel; In pyridine; ethanol; dichloromethane; chloroform; water; acetone;

DOI:10.1002/hlca.19840670427

upstream raw materials:

3β-benzyloxy-5β-androst-15-en-17-one

2-methyl-3-(3'β-benzyloxy-15'β-hydroxy-5'β-androstan-17'β-yl)furan

2-methyl-3-(3'β-benzyloxy-15'β-hydroxy-5'β-androst-16'-en-17'-yl)furan

2-methyl-3-(3'β-benzyloxy-17'β-hydroxy-5'β-androst-15'-en-17'α-yl)furan