Acetic acid (3S,3aR,3bS,7aR,8S,8aR)-3-benzyloxy-3a-hydroxy-2,2,7a-trimethyl-5-oxo-1,2,3,3a,3b,4,5,7a,8,8a-decahydro-cyclopenta[a]inden-8-yl ester

Base Information

Chemical Name:Acetic acid (3S,3aR,3bS,7aR,8S,8aR)-3-benzyloxy-3a-hydroxy-2,2,7a-trimethyl-5-oxo-1,2,3,3a,3b,4,5,7a,8,8a-decahydro-cyclopenta[a]inden-8-yl ester
CAS No.:177315-40-1
Molecular Formula:C₂₄H₃₀O₅
Molecular Weight:398.499
Hs Code.:

Synonyms:Acetic acid (3S,3aR,3bS,7aR,8S,8aR)-3-benzyloxy-3a-hydroxy-2,2,7a-trimethyl-5-oxo-1,2,3,3a,3b,4,5,7a,8,8a-decahydro-cyclopenta[a]inden-8-yl ester

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Chemical Property of Acetic acid (3S,3aR,3bS,7aR,8S,8aR)-3-benzyloxy-3a-hydroxy-2,2,7a-trimethyl-5-oxo-1,2,3,3a,3b,4,5,7a,8,8a-decahydro-cyclopenta[a]inden-8-yl ester

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Technology Process of Acetic acid (3S,3aR,3bS,7aR,8S,8aR)-3-benzyloxy-3a-hydroxy-2,2,7a-trimethyl-5-oxo-1,2,3,3a,3b,4,5,7a,8,8a-decahydro-cyclopenta[a]inden-8-yl ester

There total 10 articles about Acetic acid (3S,3aR,3bS,7aR,8S,8aR)-3-benzyloxy-3a-hydroxy-2,2,7a-trimethyl-5-oxo-1,2,3,3a,3b,4,5,7a,8,8a-decahydro-cyclopenta[a]inden-8-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: 67.0%

: 177315-35-4
Acetic acid (S)-((1R,3S)-3-benzyloxy-4,4-dimethyl-2-oxo-cyclopentyl)-(1-methyl-4-oxo-cyclohexa-2,5-dienyl)-methyl ester

: 177315-40-1
Acetic acid (3S,3aR,3bS,7aR,8S,8aR)-3-benzyloxy-3a-hydroxy-2,2,7a-trimethyl-5-oxo-1,2,3,3a,3b,4,5,7a,8,8a-decahydro-cyclopenta[a]inden-8-yl ester

Guidance literature:: With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide; In tetrahydrofuran; methanol; at -85 ℃; for 3.5h;
DOI:10.1016/0040-4020(96)00270-0

Reference yield:

: 100-39-0
benzyl bromide

: 177315-40-1
Acetic acid (3S,3aR,3bS,7aR,8S,8aR)-3-benzyloxy-3a-hydroxy-2,2,7a-trimethyl-5-oxo-1,2,3,3a,3b,4,5,7a,8,8a-decahydro-cyclopenta[a]inden-8-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) NaH / 1.) DMF, RT, 15 min, 2.) DMF, 15 min

2: 90 percent / CaCO₃, aq. HgCl₂ / acetone; H₂O / 2 h / Heating

3: 1.) diisopropyl amine, n-BuLi / 1.) THF, -40 deg C, 1 h, 2.) THF, -78 deg C, 5 min

4: 95 percent / pyridine, DMAP / 1 h / Ambient temperature

5: 79 percent / PDC, t-BuOOH / CH₂Cl₂ / 48 h / -20 °C

6: 67 percent / SmI₂, HMPA / methanol; tetrahydrofuran / 3.5 h / -85 °C

With pyridine; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; dipyridinium dichromate; n-butyllithium; samarium diiodide; sodium hydride; diisopropylamine; calcium carbonate; mercury dichloride; In tetrahydrofuran; methanol; dichloromethane; water; acetone;
DOI:10.1016/0040-4020(96)00270-0

Reference yield:

: 92640-81-8
2,2-Dimethyl-6,10-dithiaspiro<4,5>decan-1-ol

: 177315-40-1
Acetic acid (3S,3aR,3bS,7aR,8S,8aR)-3-benzyloxy-3a-hydroxy-2,2,7a-trimethyl-5-oxo-1,2,3,3a,3b,4,5,7a,8,8a-decahydro-cyclopenta[a]inden-8-yl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 100 percent / pyridine, DMAP

3: 98 percent / aq. K₂CO₃ / methanol / 2 h / 0 °C

4: 1.) NaH / 1.) DMF, RT, 15 min, 2.) DMF, 15 min

5: 90 percent / CaCO₃, aq. HgCl₂ / acetone; H₂O / 2 h / Heating

6: 1.) diisopropyl amine, n-BuLi / 1.) THF, -40 deg C, 1 h, 2.) THF, -78 deg C, 5 min

7: 95 percent / pyridine, DMAP / 1 h / Ambient temperature

8: 79 percent / PDC, t-BuOOH / CH₂Cl₂ / 48 h / -20 °C

9: 67 percent / SmI₂, HMPA / methanol; tetrahydrofuran / 3.5 h / -85 °C

With pyridine; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; dipyridinium dichromate; n-butyllithium; samarium diiodide; sodium hydride; potassium carbonate; diisopropylamine; calcium carbonate; mercury dichloride; In tetrahydrofuran; methanol; dichloromethane; water; acetone;
DOI:10.1016/0040-4020(96)00270-0