2,2-Dimethyl-propionic acid (2R,3aS,5aR,6R,8aS,8bR)-6-[2-(4-methoxy-benzyloxy)-ethyl]-7-oxo-1,2,3,3a,5a,6,7,8,8a,8b-decahydro-as-indacen-2-yl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (2R,3aS,5aR,6R,8aS,8bR)-6-[2-(4-methoxy-benzyloxy)-ethyl]-7-oxo-1,2,3,3a,5a,6,7,8,8a,8b-decahydro-as-indacen-2-yl ester
• CAS No.: 188910-76-1
• Molecular Formula: C₂₇H₃₆O₅
• Molecular Weight: 440.58
• Mol file: 188910-76-1.mol

Synonyms:2,2-Dimethyl-propionic acid (2R,3aS,5aR,6R,8aS,8bR)-6-[2-(4-methoxy-benzyloxy)-ethyl]-7-oxo-1,2,3,3a,5a,6,7,8,8a,8b-decahydro-as-indacen-2-yl ester

Chemical Property of 2,2-Dimethyl-propionic acid (2R,3aS,5aR,6R,8aS,8bR)-6-[2-(4-methoxy-benzyloxy)-ethyl]-7-oxo-1,2,3,3a,5a,6,7,8,8a,8b-decahydro-as-indacen-2-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (2R,3aS,5aR,6R,8aS,8bR)-6-[2-(4-methoxy-benzyloxy)-ethyl]-7-oxo-1,2,3,3a,5a,6,7,8,8a,8b-decahydro-as-indacen-2-yl ester

There total 24 articles about 2,2-Dimethyl-propionic acid (2R,3aS,5aR,6R,8aS,8bR)-6-[2-(4-methoxy-benzyloxy)-ethyl]-7-oxo-1,2,3,3a,5a,6,7,8,8a,8b-decahydro-as-indacen-2-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:

2,2-Dimethyl-propionic acid (2R,3aS,5aR,6R,7R,8aS,8bR)-7-hydroxy-6-[2-(4-methoxy-benzyloxy)-ethyl]-1,2,3,3a,5a,6,7,8,8a,8b-decahydro-as-indacen-2-yl ester (188910-85-2) → 2,2-Dimethyl-propionic acid (2R,3aS,5aR,6R,8aS,8bR)-6-[2-(4-methoxy-benzyloxy)-ethyl]-7-oxo-1,2,3,3a,5a,6,7,8,8a,8b-decahydro-as-indacen-2-yl ester (188910-76-1)

Guidance literature:

With pyridinium chlorochromate absorbed on neutral alumina; In dichloromethane; at 0 ℃;

DOI:10.1021/ja974009l

Reference yield:

(+/-)-7,7-dimethoxynorbornen-2-one (64145-56-8) → 2,2-Dimethyl-propionic acid (2R,3aS,5aR,6R,8aS,8bR)-6-[2-(4-methoxy-benzyloxy)-ethyl]-7-oxo-1,2,3,3a,5a,6,7,8,8a,8b-decahydro-as-indacen-2-yl ester (188910-76-1)

Guidance literature:

Multi-step reaction with 23 steps

2: 1.) t-BuLi, 2.) CeCl₃

3: 77 percent / NaH / tetrahydrofuran / 2 h / Heating

4: DIBAL-H / hexane / 0.17 h / -78 °C

5: TsOH, H₂O / acetone

6: 71 percent / (i-Pr)2NEt / CH₂Cl₂ / 18 h

7: 78 percent / K₂CO₃ / methanol / 2 h / Heating

8: 62 percent / Li, NH₃ liq., t-BuOH / tetrahydrofuran / 4 h / 20 °C

9: 1.) NaH / 1.) THF, 20 min, 2.) THF, a) from 30 to 40 deg C, 1 h, b) reflux, 3 h

10: 93 percent / LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

11: 97 percent / LiAlH₄ / diethyl ether / 0.17 h / 0 °C

12: 1.) NaH / 1.) DMF, THF, -20 deg C, 15 min, 2.) DMF, THF, a) RT, overnight, b) 40 deg C, 2 h

13: 1.) LiBH₄, BF₃*THF, 2.) 3N aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, from -30 to -20 deg C, 4.5 h, 2.) THF, RT, 1 h

14: 96 percent / imidazole, DMAP / CH₂Cl₂ / 0 °C

15: 51 percent / B-bromocatecholborane / CH₂Cl₂ / 0.25 h / -78 °C

16: 86 percent / PCC on alumina / CH₂Cl₂ / 2 h

17: NaH / tetrahydrofuran / -78 °C

18: DIBAL-H / CH₂Cl₂; hexane / 0.17 h / -78 °C

19: Martin's sulfurane / CH₂Cl₂ / 1 h

20: aq. AcOH / tetrahydrofuran

21: 97 percent / DMAP, pyridine / 0 °C

22: 97 percent / TBAF / tetrahydrofuran / 4 h / 40 °C

23: 9 mg / PCC on alumina / CH₂Cl₂ / 0 °C

With pyridine; 1H-imidazole; dmap; sodium hydroxide; pyridinium chlorochromate absorbed on neutral alumina; lithium aluminium tetrahydride; lithium borohydride; cerium(III) chloride; Martins sulfurane; boron trifluoride-tetrahydrofuran complex; bromocatecholborane; tetrabutyl ammonium fluoride; ammonia; water; dihydrogen peroxide; tert.-butyl lithium; lithium; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; N-ethyl-N,N-diisopropylamine; tert-butyl alcohol; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetone;

DOI:10.1021/ja974009l

Reference yield:

p-methoxybenzyl chloride (824-94-2) → 2,2-Dimethyl-propionic acid (2R,3aS,5aR,6R,8aS,8bR)-6-[2-(4-methoxy-benzyloxy)-ethyl]-7-oxo-1,2,3,3a,5a,6,7,8,8a,8b-decahydro-as-indacen-2-yl ester (188910-76-1)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) NaH / 1.) DMF, THF, -20 deg C, 15 min, 2.) DMF, THF, a) RT, overnight, b) 40 deg C, 2 h

2: 1.) LiBH₄, BF₃*THF, 2.) 3N aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, from -30 to -20 deg C, 4.5 h, 2.) THF, RT, 1 h

3: 96 percent / imidazole, DMAP / CH₂Cl₂ / 0 °C

4: 51 percent / B-bromocatecholborane / CH₂Cl₂ / 0.25 h / -78 °C

5: 86 percent / PCC on alumina / CH₂Cl₂ / 2 h

6: NaH / tetrahydrofuran / -78 °C

7: DIBAL-H / CH₂Cl₂; hexane / 0.17 h / -78 °C

8: Martin's sulfurane / CH₂Cl₂ / 1 h

9: aq. AcOH / tetrahydrofuran

10: 97 percent / DMAP, pyridine / 0 °C

11: 97 percent / TBAF / tetrahydrofuran / 4 h / 40 °C

12: 9 mg / PCC on alumina / CH₂Cl₂ / 0 °C

With pyridine; 1H-imidazole; dmap; sodium hydroxide; pyridinium chlorochromate absorbed on neutral alumina; lithium borohydride; Martins sulfurane; boron trifluoride-tetrahydrofuran complex; bromocatecholborane; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium hydride; diisobutylaluminium hydride; acetic acid; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/ja974009l

upstream raw materials:

2,2-Dimethyl-propionic acid (2R,3aS,5aR,6R,7R,8aS,8bR)-7-hydroxy-6-[2-(4-methoxy-benzyloxy)-ethyl]-1,2,3,3a,5a,6,7,8,8a,8b-decahydro-as-indacen-2-yl ester

(+/-)-7,7-dimethoxynorbornen-2-one

p-methoxybenzyl chloride

(3aR,5S,5aS,7S,8aR,8bS)-7-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-4,5,5a,6,7,8,8a,8b-octahydro-3aH-as-indacen-3-one

Downstream raw materials:

2,2-Dimethyl-propionic acid (2R,3aS,5aR,6S,8aS,8bR)-6-[2-(4-methoxy-benzyloxy)-ethyl]-7-oxo-1,2,3,3a,5a,6,7,8,8a,8b-decahydro-as-indacen-2-yl ester