Technology Process of (2S,5aS,7R,8S,11aR)-8-Benzyloxy-2-[(3aS,4aS,6R,7R,8S,8aS,10aR)-8-benzyloxy-7-(4-methoxy-benzyloxy)-2,2-dimethyl-octahydro-1,3,5,9-tetraoxa-benzo[f]azulen-6-ylmethyl]-7-benzyloxymethyl-octahydro-1,6-dioxa-cycloheptacycloocten-3-one
There total 19 articles about (2S,5aS,7R,8S,11aR)-8-Benzyloxy-2-[(3aS,4aS,6R,7R,8S,8aS,10aR)-8-benzyloxy-7-(4-methoxy-benzyloxy)-2,2-dimethyl-octahydro-1,3,5,9-tetraoxa-benzo[f]azulen-6-ylmethyl]-7-benzyloxymethyl-octahydro-1,6-dioxa-cycloheptacycloocten-3-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:
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725253-61-2
(2S,5aS,7R,8S,11aR)-8-Benzyloxy-2-[(3aS,4aS,6R,7R,8S,8aS,10aR)-8-benzyloxy-7-(4-methoxy-benzyloxy)-2,2-dimethyl-octahydro-1,3,5,9-tetraoxa-benzo[f]azulen-6-ylmethyl]-7-benzyloxymethyl-decahydro-1,6-dioxa-cycloheptacycloocten-3-ol
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725253-49-6
(2S,5aS,7R,8S,11aR)-8-Benzyloxy-2-[(3aS,4aS,6R,7R,8S,8aS,10aR)-8-benzyloxy-7-(4-methoxy-benzyloxy)-2,2-dimethyl-octahydro-1,3,5,9-tetraoxa-benzo[f]azulen-6-ylmethyl]-7-benzyloxymethyl-octahydro-1,6-dioxa-cycloheptacycloocten-3-one
- Guidance literature:
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With
N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve;
In
dichloromethane;
at 20 ℃;
DOI:10.1016/j.tetlet.2004.04.083
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252046-22-3
(2R,3R,4S,4aS,9aS)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-2,3,4,4a,9,9a-hexahydro-6H-pyrano[3,2-b]oxepin
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725253-49-6
(2S,5aS,7R,8S,11aR)-8-Benzyloxy-2-[(3aS,4aS,6R,7R,8S,8aS,10aR)-8-benzyloxy-7-(4-methoxy-benzyloxy)-2,2-dimethyl-octahydro-1,3,5,9-tetraoxa-benzo[f]azulen-6-ylmethyl]-7-benzyloxymethyl-octahydro-1,6-dioxa-cycloheptacycloocten-3-one
- Guidance literature:
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Multi-step reaction with 11 steps
1.1: AD-mix β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O; various solvent(s) / 0 °C
2.1: CSA / CH2Cl2 / 20 °C
3.1: H2 / Pd/C / ethyl acetate; methanol / 20 °C
4.1: CSA / CH2Cl2 / 20 °C
5.1: 92 percent / KOt-Bu; n-Bu4NI / tetrahydrofuran / 20 °C
6.1: 100 percent / DIBAL-H / CH2Cl2 / -78 - 0 °C
7.1: 92 percent / I2; PPh3; imidazole / tetrahydrofuran / 20 °C
8.1: 99 percent / NaH / dimethylformamide / 0 - 20 °C
9.1: 9-BBN / tetrahydrofuran / 20 °C
9.2: aq. Cs2CO3 / PdCl2(dppf)*CH2Cl2 / tetrahydrofuran; dimethylformamide / 50 °C
10.1: thexylborane / tetrahydrofuran / 0 °C
10.2: 78 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 20 °C
11.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 20 °C
With
1H-imidazole; 9-borabicyclo[3.3.1]nonane dimer; N-methyl-2-indolinone; tetrapropylammonium perruthennate; methanesulfonamide; 4 A molecular sieve; thexylborane; camphor-10-sulfonic acid; potassium tert-butylate; hydrogen; iodine; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; 1,4-bis(9-O-dihydroquinidine)phthalazine; triphenylphosphine;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol;
9.1: Suzuki-Miyaura coupling / 9.2: Suzuki-Miyaura coupling;
DOI:10.1016/j.tetlet.2004.04.083
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725253-39-4
(3aS,4aS,6R,7R,8R,8aS,10aR)-7,8-Bis-benzyloxy-6-benzyloxymethyl-2,2-dimethyl-octahydro-1,3,5,9-tetraoxa-benzo[f]azulene
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725253-49-6
(2S,5aS,7R,8S,11aR)-8-Benzyloxy-2-[(3aS,4aS,6R,7R,8S,8aS,10aR)-8-benzyloxy-7-(4-methoxy-benzyloxy)-2,2-dimethyl-octahydro-1,3,5,9-tetraoxa-benzo[f]azulen-6-ylmethyl]-7-benzyloxymethyl-octahydro-1,6-dioxa-cycloheptacycloocten-3-one
- Guidance literature:
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Multi-step reaction with 9 steps
1.1: H2 / Pd/C / ethyl acetate; methanol / 20 °C
2.1: CSA / CH2Cl2 / 20 °C
3.1: 92 percent / KOt-Bu; n-Bu4NI / tetrahydrofuran / 20 °C
4.1: 100 percent / DIBAL-H / CH2Cl2 / -78 - 0 °C
5.1: 92 percent / I2; PPh3; imidazole / tetrahydrofuran / 20 °C
6.1: 99 percent / NaH / dimethylformamide / 0 - 20 °C
7.1: 9-BBN / tetrahydrofuran / 20 °C
7.2: aq. Cs2CO3 / PdCl2(dppf)*CH2Cl2 / tetrahydrofuran; dimethylformamide / 50 °C
8.1: thexylborane / tetrahydrofuran / 0 °C
8.2: 78 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 20 °C
9.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 20 °C
With
1H-imidazole; 9-borabicyclo[3.3.1]nonane dimer; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; thexylborane; camphor-10-sulfonic acid; potassium tert-butylate; hydrogen; iodine; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; triphenylphosphine;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
7.1: Suzuki-Miyaura coupling / 7.2: Suzuki-Miyaura coupling;
DOI:10.1016/j.tetlet.2004.04.083