(4aS,5S,6R,8R,8aS)-8-Benzyloxy-5-(2-benzyloxy-ethyl)-3,4a,6-trimethyl-4a,5,6,7,8,8a-hexahydro-1H-naphthalen-2-one

Base Information

Chemical Name:(4aS,5S,6R,8R,8aS)-8-Benzyloxy-5-(2-benzyloxy-ethyl)-3,4a,6-trimethyl-4a,5,6,7,8,8a-hexahydro-1H-naphthalen-2-one
CAS No.:135041-56-4
Molecular Formula:C₂₉H₃₆O₃
Molecular Weight:432.603
Hs Code.:

Synonyms:(4aS,5S,6R,8R,8aS)-8-Benzyloxy-5-(2-benzyloxy-ethyl)-3,4a,6-trimethyl-4a,5,6,7,8,8a-hexahydro-1H-naphthalen-2-one

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Chemical Property of (4aS,5S,6R,8R,8aS)-8-Benzyloxy-5-(2-benzyloxy-ethyl)-3,4a,6-trimethyl-4a,5,6,7,8,8a-hexahydro-1H-naphthalen-2-one

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Technology Process of (4aS,5S,6R,8R,8aS)-8-Benzyloxy-5-(2-benzyloxy-ethyl)-3,4a,6-trimethyl-4a,5,6,7,8,8a-hexahydro-1H-naphthalen-2-one

There total 15 articles about (4aS,5S,6R,8R,8aS)-8-Benzyloxy-5-(2-benzyloxy-ethyl)-3,4a,6-trimethyl-4a,5,6,7,8,8a-hexahydro-1H-naphthalen-2-one 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: 53.0%

: 135041-57-5,135041-63-3
(4aS,5S,6R,8R,8aS)-8-Benzyloxy-5-(2-benzyloxy-ethyl)-1-bromo-3,4a,6-trimethyl-4a,5,6,7,8,8a-hexahydro-1H-naphthalen-2-one

: 135041-56-4
(4aS,5S,6R,8R,8aS)-8-Benzyloxy-5-(2-benzyloxy-ethyl)-3,4a,6-trimethyl-4a,5,6,7,8,8a-hexahydro-1H-naphthalen-2-one

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 24h; Heating;
DOI:10.1021/ja00015a064

Reference yield:

: 527-61-7
2,6-dimethyl-1,4-benzoquinone

: 135041-56-4
(4aS,5S,6R,8R,8aS)-8-Benzyloxy-5-(2-benzyloxy-ethyl)-3,4a,6-trimethyl-4a,5,6,7,8,8a-hexahydro-1H-naphthalen-2-one

Guidance literature:: Multi-step reaction with 12 steps

1: 1.) BF₃*Et₂O, 2.) Zn, HOAc / 1.) 96 h, 2.) reflux, 18 h

2: 1.) L-Selectride, 2.) NaOH, H₂O₂ / 1.) THF, -78 deg C, 2.) THF, 0 deg C

3: 83 percent / NaH, Bu₄NI / tetrahydrofuran / 72 h

4: 1.) sec-BuLi / 1.) THF, from -60 deg C to -20 deg C, 1 h, 2.) THF, -40 deg C, 30 min

5: ethanol

6: 1.) KOtBu / 1.) THF, 0 deg C, 1 h, 2.) THF, RT, 18 h

7: disiamylborane / tetrahydrofuran / 72 h / 40 °C

8: H₂O₂, NaOH / 0 °C

9: 98 percent / NaH, Bu₄NI / tetrahydrofuran / 48 h

10: 1.) BH₃*THF, 2.) NaOH, H₂O₂ / 1.) 0 deg C, 6 h

11: 90 percent / (COCl)2, DMSO / CH₂Cl₂

12: 1.) pyridinium bromide perbromide, 2.) LiBr, Li₂CO₃ / 1.) THF, -78 deg C, 30 min, 2.) DMF, 120 deg C, 16 h

With sodium hydroxide; borane-THF; oxalyl dichloride; boron trifluoride diethyl etherate; potassium tert-butylate; dihydrogen peroxide; sec.-butyllithium; pyridinium hydrobromide perbromide; bis-(1,2-dimethylpropyl)borane; tetra-(n-butyl)ammonium iodide; lithium carbonate; L-Selectride; sodium hydride; acetic acid; dimethyl sulfoxide; lithium bromide; zinc; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1021/ja00015a064

Reference yield:

: 100-39-0
benzyl bromide

: 135041-56-4
(4aS,5S,6R,8R,8aS)-8-Benzyloxy-5-(2-benzyloxy-ethyl)-3,4a,6-trimethyl-4a,5,6,7,8,8a-hexahydro-1H-naphthalen-2-one

Guidance literature:: Multi-step reaction with 10 steps

1: 83 percent / NaH, Bu₄NI / tetrahydrofuran / 72 h

2: 1.) sec-BuLi / 1.) THF, from -60 deg C to -20 deg C, 1 h, 2.) THF, -40 deg C, 30 min

3: ethanol

4: 1.) KOtBu / 1.) THF, 0 deg C, 1 h, 2.) THF, RT, 18 h

5: disiamylborane / tetrahydrofuran / 72 h / 40 °C

6: H₂O₂, NaOH / 0 °C

7: 98 percent / NaH, Bu₄NI / tetrahydrofuran / 48 h

8: 1.) BH₃*THF, 2.) NaOH, H₂O₂ / 1.) 0 deg C, 6 h

9: 90 percent / (COCl)2, DMSO / CH₂Cl₂

10: 1.) pyridinium bromide perbromide, 2.) LiBr, Li₂CO₃ / 1.) THF, -78 deg C, 30 min, 2.) DMF, 120 deg C, 16 h

With sodium hydroxide; borane-THF; oxalyl dichloride; potassium tert-butylate; dihydrogen peroxide; sec.-butyllithium; pyridinium hydrobromide perbromide; bis-(1,2-dimethylpropyl)borane; tetra-(n-butyl)ammonium iodide; lithium carbonate; sodium hydride; dimethyl sulfoxide; lithium bromide; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1021/ja00015a064