4-(3'β-benzyloxy-15'β-hydroxy-5'β-androstan-17'β-yl)-3-oxo-3,6-dihydro-2H-pyran-6-yl acetate

Base Information

Chemical Name:4-(3'β-benzyloxy-15'β-hydroxy-5'β-androstan-17'β-yl)-3-oxo-3,6-dihydro-2H-pyran-6-yl acetate
CAS No.:86708-94-3
Molecular Formula:C₃₃H₄₄O₆
Molecular Weight:536.709
Hs Code.:

Synonyms:4-(3'β-benzyloxy-15'β-hydroxy-5'β-androstan-17'β-yl)-3-oxo-3,6-dihydro-2H-pyran-6-yl acetate

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Chemical Property of 4-(3'β-benzyloxy-15'β-hydroxy-5'β-androstan-17'β-yl)-3-oxo-3,6-dihydro-2H-pyran-6-yl acetate

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Technology Process of 4-(3'β-benzyloxy-15'β-hydroxy-5'β-androstan-17'β-yl)-3-oxo-3,6-dihydro-2H-pyran-6-yl acetate

There total 8 articles about 4-(3'β-benzyloxy-15'β-hydroxy-5'β-androstan-17'β-yl)-3-oxo-3,6-dihydro-2H-pyran-6-yl acetate 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: 90.0%

: 108-24-7
acetic anhydride

: 83457-13-0
4-(3'β-benzyloxy-15'β-hydroxy-5'β-androstan-17'β-yl)-6-hydroxy-3,6-dihydro-2H-pyran-3-one

: 86708-94-3
4-(3'β-benzyloxy-15'β-hydroxy-5'β-androstan-17'β-yl)-3-oxo-3,6-dihydro-2H-pyran-6-yl acetate

Guidance literature:: With sodium acetate; In benzene; for 1h; Heating;
DOI:10.1002/hlca.19820650712

Reference yield:

: 73336-58-0
3β-benzyloxy-5β-androst-15-en-17-one

: 86708-94-3
4-(3'β-benzyloxy-15'β-hydroxy-5'β-androstan-17'β-yl)-3-oxo-3,6-dihydro-2H-pyran-6-yl acetate

Guidance literature:: Multi-step reaction with 8 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

With hydrogenchloride; sodium tetrahydroborate; n-butyllithium; hydrogen; sodium acetate; 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:

: 83457-09-4
3-(3'β-benzyloxy-17'β-hydroxy-5'β-androst-15'-en-17'α-yl)furan-2-carbaldehyde ethylene acetal

: 86708-94-3
4-(3'β-benzyloxy-15'β-hydroxy-5'β-androstan-17'β-yl)-3-oxo-3,6-dihydro-2H-pyran-6-yl acetate

Guidance literature:: Multi-step reaction with 7 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

With hydrogenchloride; sodium tetrahydroborate; hydrogen; sodium acetate; 3-chloro-benzenecarboperoxoic acid; calcium carbonate; dmap; Lindlar's catalyst; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; water; acetone; benzene;
DOI:10.1002/hlca.19820650712