4-(3'β-benzyloxy-5'β-androst-14'-en-17'β-yl)-2-oxo-5,6-dihydro-2H-pyran-5-yl methanesulfonate

Base Information

• Chemical Name: 4-(3'β-benzyloxy-5'β-androst-14'-en-17'β-yl)-2-oxo-5,6-dihydro-2H-pyran-5-yl methanesulfonate
• CAS No.: 86746-66-9
• Molecular Formula: C₃₂H₄₂O₆S
• Molecular Weight: 554.748

Synonyms:4-(3'β-benzyloxy-5'β-androst-14'-en-17'β-yl)-2-oxo-5,6-dihydro-2H-pyran-5-yl methanesulfonate

Chemical Property of 4-(3'β-benzyloxy-5'β-androst-14'-en-17'β-yl)-2-oxo-5,6-dihydro-2H-pyran-5-yl methanesulfonate

Chemical Property:

Purity/Quality:

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MSDS Files:

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Technology Process of 4-(3'β-benzyloxy-5'β-androst-14'-en-17'β-yl)-2-oxo-5,6-dihydro-2H-pyran-5-yl methanesulfonate

There total 13 articles about 4-(3'β-benzyloxy-5'β-androst-14'-en-17'β-yl)-2-oxo-5,6-dihydro-2H-pyran-5-yl methanesulfonate 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: 80.0%

methanesulfonyl chloride (124-63-0) + 4-(3'β-benzyloxy-5'β-androst-14'-en-17'β-yl)-5-hydroxy-5,6-dihydro-2H-pyran-2-one (83457-15-2) → 4-(3'β-benzyloxy-5'β-androst-14'-en-17'β-yl)-2-oxo-5,6-dihydro-2H-pyran-5-yl methanesulfonate (86746-66-9)

Guidance literature:

With triethylamine; In dichloromethane; for 0.5h; in an ice-bath;

DOI:10.1002/hlca.19820650712

Reference yield:

3β-benzyloxy-5β-androst-15-en-17-one (73336-58-0) → 4-(3'β-benzyloxy-5'β-androst-14'-en-17'β-yl)-2-oxo-5,6-dihydro-2H-pyran-5-yl methanesulfonate (86746-66-9)

Guidance literature:

Multi-step reaction with 13 steps

1: 95 percent / 1.) butyllithium / diethyl ether; benzene / 0.5 h / -70 °C

2: 4-dimethylaminopyridine / pyridine / 72 h / Ambient temperature

3: CaCO₃ / acetone; H₂O / 96 h / Heating

4: 92 percent / H₂ / 10percent Pd/CaCO₃ / ethanol / Ambient temperature

5: 1N HCl / tetrahydrofuran / 1 h

6: 95 percent / NaBH₄ / tetrahydrofuran; methanol / Ambient temperature

7: 90 percent / m-chloroperbenzoic acid, NaOAc / CH₂Cl₂ / 2 h / in an ice-bath

8: 90 percent / NaOAc / benzene / 1 h / Heating

9: 88 percent / SOCl₂ / pyridine / 1 h / in an ice-bath

10: 90 percent / 1N KOH / tetrahydrofuran; methanol / 1 h / Ambient temperature

11: CrO₃/dipyridine / CH₂Cl₂ / 0.17 h / Ambient temperature

12: Zn(BH₄)2 / diethyl ether; CH₂Cl₂ / 1 h

13: 80 percent / triethylamine / CH₂Cl₂ / 0.5 h / in an ice-bath

With chromium(VI) oxide; hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; n-butyllithium; thionyl chloride; zinc(II) tetrahydroborate; dipyridine; hydrogen; sodium acetate; triethylamine; 3-chloro-benzenecarboperoxoic acid; calcium carbonate; dmap; Lindlar's catalyst; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; water; acetone; benzene;

DOI:10.1002/hlca.19820650712

Reference yield:

3-(3'β-benzyloxy-17'β-hydroxy-5'β-androst-15'-en-17'α-yl)furan-2-carbaldehyde ethylene acetal (83457-09-4) → 4-(3'β-benzyloxy-5'β-androst-14'-en-17'β-yl)-2-oxo-5,6-dihydro-2H-pyran-5-yl methanesulfonate (86746-66-9)

Guidance literature:

Multi-step reaction with 12 steps

1: 4-dimethylaminopyridine / pyridine / 72 h / Ambient temperature

2: CaCO₃ / acetone; H₂O / 96 h / Heating

3: 92 percent / H₂ / 10percent Pd/CaCO₃ / ethanol / Ambient temperature

4: 1N HCl / tetrahydrofuran / 1 h

5: 95 percent / NaBH₄ / tetrahydrofuran; methanol / Ambient temperature

6: 90 percent / m-chloroperbenzoic acid, NaOAc / CH₂Cl₂ / 2 h / in an ice-bath

7: 90 percent / NaOAc / benzene / 1 h / Heating

8: 88 percent / SOCl₂ / pyridine / 1 h / in an ice-bath

9: 90 percent / 1N KOH / tetrahydrofuran; methanol / 1 h / Ambient temperature

10: CrO₃/dipyridine / CH₂Cl₂ / 0.17 h / Ambient temperature

11: Zn(BH₄)2 / diethyl ether; CH₂Cl₂ / 1 h

12: 80 percent / triethylamine / CH₂Cl₂ / 0.5 h / in an ice-bath

With chromium(VI) oxide; hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; thionyl chloride; zinc(II) tetrahydroborate; dipyridine; hydrogen; sodium acetate; triethylamine; 3-chloro-benzenecarboperoxoic acid; calcium carbonate; dmap; Lindlar's catalyst; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; water; acetone; benzene;

DOI:10.1002/hlca.19820650712

upstream raw materials:

methanesulfonyl chloride

4-(3'β-benzyloxy-5'β-androst-14'-en-17'β-yl)-5-hydroxy-5,6-dihydro-2H-pyran-2-one

3β-benzyloxy-5β-androst-15-en-17-one

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

Downstream raw materials:

4-(3'β-benzyloxy-5'β-androst-14'-en-17'β-yl)-2H-pyran-2-one

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