Acetic acid (8R,9S,13R,14S,15S,16S,17S)-16,17-diacetoxy-2,3-bis-benzyloxy-14-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-15-yl ester

Base Information

Chemical Name:Acetic acid (8R,9S,13R,14S,15S,16S,17S)-16,17-diacetoxy-2,3-bis-benzyloxy-14-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-15-yl ester
CAS No.:176219-98-0
Molecular Formula:C₃₈H₄₂O₉
Molecular Weight:642.746
Hs Code.:

Acetic acid (8R,9S,13R,14S,15S,16S,17S)-16,17-diacetoxy-2,3-bis-benzyloxy-14-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-15-yl ester

Synonyms:Acetic acid (8R,9S,13R,14S,15S,16S,17S)-16,17-diacetoxy-2,3-bis-benzyloxy-14-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-15-yl ester

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Chemical Property of Acetic acid (8R,9S,13R,14S,15S,16S,17S)-16,17-diacetoxy-2,3-bis-benzyloxy-14-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-15-yl ester

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Technology Process of Acetic acid (8R,9S,13R,14S,15S,16S,17S)-16,17-diacetoxy-2,3-bis-benzyloxy-14-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-15-yl ester

There total 24 articles about Acetic acid (8R,9S,13R,14S,15S,16S,17S)-16,17-diacetoxy-2,3-bis-benzyloxy-14-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-15-yl ester 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:

: 38781-50-9
2-(17β-acetoxy-2-hydroxy-estra-1,3,5(10)-trien-3-yloxy)-5-nitro-benzophenone

: 176219-98-0
Acetic acid (8R,9S,13R,14S,15S,16S,17S)-16,17-diacetoxy-2,3-bis-benzyloxy-14-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-15-yl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 99.6 percent / Na₂CO₃ / dimethylformamide / 5 h / 100 - 120 °C

2: KOH / ethanol / 2 h / Heating

3: 224 mg / Na₂CO₃ / 20 h / 100 - 120 °C

4: 56.5 percent / Jones reagent / acetone / 0.05 h

5: 93 percent / Et₃N / CH₂Cl₂ / 2 h / -78 °C

6: 71.9 percent / Pd(OAc)2, Cu(OAc)2, oxygen / acetonitrile / 17 h / 50 °C

7: 59 percent / p-TsOH*H₂O / benzene / 0.07 h / Heating

8: 1) PBA, 2) Na₂CO₃ / 1) C₆H₆, CH₂Cl₂, 3 days, 2) t-BuOH, H₂O, reflux, 1 h

9: 82.7 percent / NaBH₄, CeCl₃*7H₂O / methanol; tetrahydrofuran / 1 h

10: 1) OsO₄, N-methylmorpholine N-oxide, H₂O, 2) pyridine, DMAP / 1) acetone, 4 days, 2) 17 h

With pyridine; dmap; palladium diacetate; potassium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; jones reagent; cerium(III) chloride; copper diacetate; water; oxygen; sodium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile; benzene;
DOI:10.1271/bbb.60.405

Reference yield:

: 100-44-7
benzyl chloride

: 176219-98-0
Acetic acid (8R,9S,13R,14S,15S,16S,17S)-16,17-diacetoxy-2,3-bis-benzyloxy-14-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-15-yl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 99.6 percent / Na₂CO₃ / dimethylformamide / 5 h / 100 - 120 °C

2: KOH / ethanol / 2 h / Heating

3: 224 mg / Na₂CO₃ / 20 h / 100 - 120 °C

4: 56.5 percent / Jones reagent / acetone / 0.05 h

5: 93 percent / Et₃N / CH₂Cl₂ / 2 h / -78 °C

6: 71.9 percent / Pd(OAc)2, Cu(OAc)2, oxygen / acetonitrile / 17 h / 50 °C

7: 59 percent / p-TsOH*H₂O / benzene / 0.07 h / Heating

8: 1) PBA, 2) Na₂CO₃ / 1) C₆H₆, CH₂Cl₂, 3 days, 2) t-BuOH, H₂O, reflux, 1 h

9: 82.7 percent / NaBH₄, CeCl₃*7H₂O / methanol; tetrahydrofuran / 1 h

10: 1) OsO₄, N-methylmorpholine N-oxide, H₂O, 2) pyridine, DMAP / 1) acetone, 4 days, 2) 17 h

With pyridine; dmap; palladium diacetate; potassium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; jones reagent; cerium(III) chloride; copper diacetate; water; oxygen; sodium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile; benzene;
DOI:10.1271/bbb.60.405

Reference yield:

: 22145-26-2
(17β)-2-benzyloxy-1,3,5(10)-estratriene-3,17-diol

: 176219-98-0
Acetic acid (8R,9S,13R,14S,15S,16S,17S)-16,17-diacetoxy-2,3-bis-benzyloxy-14-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-15-yl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 224 mg / Na₂CO₃ / 20 h / 100 - 120 °C

2: 56.5 percent / Jones reagent / acetone / 0.05 h

3: 93 percent / Et₃N / CH₂Cl₂ / 2 h / -78 °C

4: 71.9 percent / Pd(OAc)2, Cu(OAc)2, oxygen / acetonitrile / 17 h / 50 °C

5: 59 percent / p-TsOH*H₂O / benzene / 0.07 h / Heating

6: 1) PBA, 2) Na₂CO₃ / 1) C₆H₆, CH₂Cl₂, 3 days, 2) t-BuOH, H₂O, reflux, 1 h

7: 82.7 percent / NaBH₄, CeCl₃*7H₂O / methanol; tetrahydrofuran / 1 h

8: 1) OsO₄, N-methylmorpholine N-oxide, H₂O, 2) pyridine, DMAP / 1) acetone, 4 days, 2) 17 h

With pyridine; dmap; palladium diacetate; sodium tetrahydroborate; osmium(VIII) oxide; jones reagent; cerium(III) chloride; copper diacetate; water; oxygen; sodium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; acetone; acetonitrile; benzene;
DOI:10.1271/bbb.60.405