(7E,9E,13E)-(3S,4R,4aR,6aS,11S,12R,18R,20aR,20bS)-4-Hydroxy-13-(4-methoxy-benzyloxymethyl)-12-methoxymethoxy-3,6,11,18,20a-pentamethyl-1,2,3,4,4a,6a,11,12,15,16,17,18,20a,20b-tetradecahydro-19-oxa-cyclohexadeca[a]naphthalen-20-one

Base Information

Chemical Name:(7E,9E,13E)-(3S,4R,4aR,6aS,11S,12R,18R,20aR,20bS)-4-Hydroxy-13-(4-methoxy-benzyloxymethyl)-12-methoxymethoxy-3,6,11,18,20a-pentamethyl-1,2,3,4,4a,6a,11,12,15,16,17,18,20a,20b-tetradecahydro-19-oxa-cyclohexadeca[a]naphthalen-20-one
CAS No.:885218-93-9
Molecular Formula:C₃₉H₅₆O₇
Molecular Weight:636.869
Hs Code.:

(7E,9E,13E)-(3S,4R,4aR,6aS,11S,12R,18R,20aR,20bS)-4-Hydroxy-13-(4-methoxy-benzyloxymethyl)-12-methoxymethoxy-3,6,11,18,20a-pentamethyl-1,2,3,4,4a,6a,11,12,15,16,17,18,20a,20b-tetradecahydro-19-oxa-cyclohexadeca[a]naphthalen-20-one

Synonyms:(7E,9E,13E)-(3S,4R,4aR,6aS,11S,12R,18R,20aR,20bS)-4-Hydroxy-13-(4-methoxy-benzyloxymethyl)-12-methoxymethoxy-3,6,11,18,20a-pentamethyl-1,2,3,4,4a,6a,11,12,15,16,17,18,20a,20b-tetradecahydro-19-oxa-cyclohexadeca[a]naphthalen-20-one

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Chemical Property of (7E,9E,13E)-(3S,4R,4aR,6aS,11S,12R,18R,20aR,20bS)-4-Hydroxy-13-(4-methoxy-benzyloxymethyl)-12-methoxymethoxy-3,6,11,18,20a-pentamethyl-1,2,3,4,4a,6a,11,12,15,16,17,18,20a,20b-tetradecahydro-19-oxa-cyclohexadeca[a]naphthalen-20-one

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Technology Process of (7E,9E,13E)-(3S,4R,4aR,6aS,11S,12R,18R,20aR,20bS)-4-Hydroxy-13-(4-methoxy-benzyloxymethyl)-12-methoxymethoxy-3,6,11,18,20a-pentamethyl-1,2,3,4,4a,6a,11,12,15,16,17,18,20a,20b-tetradecahydro-19-oxa-cyclohexadeca[a]naphthalen-20-one

There total 25 articles about (7E,9E,13E)-(3S,4R,4aR,6aS,11S,12R,18R,20aR,20bS)-4-Hydroxy-13-(4-methoxy-benzyloxymethyl)-12-methoxymethoxy-3,6,11,18,20a-pentamethyl-1,2,3,4,4a,6a,11,12,15,16,17,18,20a,20b-tetradecahydro-19-oxa-cyclohexadeca[a]naphthalen-20-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: 80.0%

: 885218-92-8
(1R,2S,4aR,5R,6S,8aS)-5-Hydroxy-2-[(1E,3E,7E)-(5S,6R,12R)-12-hydroxy-7-(4-methoxy-benzyloxymethyl)-6-methoxymethoxy-5-methyl-trideca-1,3,7-trienyl]-1,3,6-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid

: 885218-93-9
(7E,9E,13E)-(3S,4R,4aR,6aS,11S,12R,18R,20aR,20bS)-4-Hydroxy-13-(4-methoxy-benzyloxymethyl)-12-methoxymethoxy-3,6,11,18,20a-pentamethyl-1,2,3,4,4a,6a,11,12,15,16,17,18,20a,20b-tetradecahydro-19-oxa-cyclohexadeca[a]naphthalen-20-one

Guidance literature:: With dmap; 2-methyl-6-nitrobenzoic anhydride; In dichloromethane; at 20 ℃; for 12h;
DOI:10.1016/j.tetlet.2006.01.140

Reference yield:

: (4S,5S)-4-Hydroxy-5-(4-methoxy-benzyloxymethyl)-dihydro-furan-2-one

: 885218-93-9
(7E,9E,13E)-(3S,4R,4aR,6aS,11S,12R,18R,20aR,20bS)-4-Hydroxy-13-(4-methoxy-benzyloxymethyl)-12-methoxymethoxy-3,6,11,18,20a-pentamethyl-1,2,3,4,4a,6a,11,12,15,16,17,18,20a,20b-tetradecahydro-19-oxa-cyclohexadeca[a]naphthalen-20-one

Guidance literature:: Multi-step reaction with 14 steps

1.1: LDA / tetrahydrofuran / 6 h / -78 - 20 °C

2.1: i-Pr₂NEt / acetonitrile / 4 h / 50 °C

2.2: 85 percent / LAH / tetrahydrofuran / 0.5 h / 0 °C

3.1: Et₃N / 1,2-dichloro-ethane / 12 h / 50 °C

3.2: 90 percent / IBX / toluene; dimethylsulfoxide / 0.5 h / 50 °C

4.1: 65 percent / t-BuLi / tetrahydrofuran / 1 h / -78 - 20 °C

5.1: 75 percent / BF₃OEt₂ / CH₂Cl₂ / 1 h / 0 °C

6.1: PdCl₂ / dimethylformamide; H₂O / 12 h / 0 °C

7.1: IBX / toluene; dimethylsulfoxide / 3 h / 50 °C

8.1: PPh₃ / CH₂Cl₂ / 0.17 h / 0 °C

9.1: (S)-CBS; catecholborane / tetrahydrofuran; CH₂Cl₂ / 8 h / -78 °C

10.1: n-BuLi / tetrahydrofuran / 0.17 h / 0 °C

11.1: 61 percent / catecholborane / tetrahydrofuran / 72 h / Heating

12.1: 35 percent / AsPh₃; TlOEt / Pd₂(dba)3 / tetrahydrofuran; H₂O / 0.17 h / 20 °C

13.1: 95 percent / TBAF / tetrahydrofuran / 3 h / 0 - 20 °C

14.1: 80 percent / MNBA; DMAP / CH₂Cl₂ / 12 h / 20 °C

With dmap; n-butyllithium; (S)-diphenylprolinol; triphenyl-arsane; boron trifluoride diethyl etherate; 2-methyl-6-nitrobenzoic anhydride; tetrabutyl ammonium fluoride; tert.-butyl lithium; thallium (I) ethoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium diisopropyl amide; benzo[1,3,2]dioxaborole; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; palladium dichloride; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile; 6.1: Wacker oxidation / 12.1: Suzuki-Miyaura coupling / 14.1: Shiina macrolactonization;
DOI:10.1016/j.tetlet.2006.01.140

Reference yield:

: (3R,4S,5S)-4-Hydroxy-5-(4-methoxy-benzyloxymethyl)-3-methyl-dihydro-furan-2-one

: 885218-93-9
(7E,9E,13E)-(3S,4R,4aR,6aS,11S,12R,18R,20aR,20bS)-4-Hydroxy-13-(4-methoxy-benzyloxymethyl)-12-methoxymethoxy-3,6,11,18,20a-pentamethyl-1,2,3,4,4a,6a,11,12,15,16,17,18,20a,20b-tetradecahydro-19-oxa-cyclohexadeca[a]naphthalen-20-one

Guidance literature:: Multi-step reaction with 13 steps

1.1: i-Pr₂NEt / acetonitrile / 4 h / 50 °C

1.2: 85 percent / LAH / tetrahydrofuran / 0.5 h / 0 °C

2.1: Et₃N / 1,2-dichloro-ethane / 12 h / 50 °C

2.2: 90 percent / IBX / toluene; dimethylsulfoxide / 0.5 h / 50 °C

3.1: 65 percent / t-BuLi / tetrahydrofuran / 1 h / -78 - 20 °C

4.1: 75 percent / BF₃OEt₂ / CH₂Cl₂ / 1 h / 0 °C

5.1: PdCl₂ / dimethylformamide; H₂O / 12 h / 0 °C

6.1: IBX / toluene; dimethylsulfoxide / 3 h / 50 °C

7.1: PPh₃ / CH₂Cl₂ / 0.17 h / 0 °C

8.1: (S)-CBS; catecholborane / tetrahydrofuran; CH₂Cl₂ / 8 h / -78 °C

9.1: n-BuLi / tetrahydrofuran / 0.17 h / 0 °C

10.1: 61 percent / catecholborane / tetrahydrofuran / 72 h / Heating

11.1: 35 percent / AsPh₃; TlOEt / Pd₂(dba)3 / tetrahydrofuran; H₂O / 0.17 h / 20 °C

12.1: 95 percent / TBAF / tetrahydrofuran / 3 h / 0 - 20 °C

13.1: 80 percent / MNBA; DMAP / CH₂Cl₂ / 12 h / 20 °C

With dmap; n-butyllithium; (S)-diphenylprolinol; triphenyl-arsane; boron trifluoride diethyl etherate; 2-methyl-6-nitrobenzoic anhydride; tetrabutyl ammonium fluoride; tert.-butyl lithium; thallium (I) ethoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; benzo[1,3,2]dioxaborole; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; palladium dichloride; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile; 5.1: Wacker oxidation / 11.1: Suzuki-Miyaura coupling / 13.1: Shiina macrolactonization;
DOI:10.1016/j.tetlet.2006.01.140