Technology Process of Methanesulfonic acid (1R,2R,9S,9aS)-5,8-bis-benzyloxy-9-benzyloxymethyl-2-(dimethoxy-phosphorylamino)-7-methoxy-6-methyl-2,3,9,9a-tetrahydro-1H-pyrrolo[1,2-a]indol-1-yl ester
There total 20 articles about Methanesulfonic acid (1R,2R,9S,9aS)-5,8-bis-benzyloxy-9-benzyloxymethyl-2-(dimethoxy-phosphorylamino)-7-methoxy-6-methyl-2,3,9,9a-tetrahydro-1H-pyrrolo[1,2-a]indol-1-yl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 10 steps
1: 55 percent / n-BuLi / tetrahydrofuran / -75 - 0 °C
2: 69 percent / cerium(IV) ammonium nitrate / H2O; acetonitrile / 0.05 h / 0 °C
3: 88 percent / NaN3 / H2O; methanol / 1 h
4: 49 percent / Cu(acac)2 / benzene / 2 h / 80 °C
5: 1.) zinc powder, AcOH, 2.) K2CO3 / 1.) CH2Cl2, 2.) DMF, reflux 12 h
6: 76 percent / N-methylmorpholine oxide / OsO4 / H2O; 2-methyl-propan-2-ol / 12 h
7: Et3N / CH2Cl2 / 2 h / 0 °C
8: 56 percent / n-Bu4NN3 / benzene / 3 h / Heating
9: Et3N / CH2Cl2 / 2 h / 0 °C
10: tetrahydrofuran / 4 h / Heating
With
copper acetylacetonate; n-butyllithium; sodium azide; ammonium cerium(IV) nitrate; tetrabutylammoniun azide; potassium carbonate; acetic acid; 4-methylmorpholine N-oxide; triethylamine; zinc;
osmium(VIII) oxide;
In
tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; tert-butyl alcohol; benzene;
- Guidance literature:
-
Multi-step reaction with 18 steps
1: 80 percent / Br2
2: 1.) m-chloroperbenzoic acid, 2.) KOH / 2.) MeOH
3: NaH / dimethylformamide
4: n-BuLi, perchloryl fluoride / diethyl ether
5: HCl / acetone
6: 83 percent / K2CO3 / acetone
7: 62 percent / AlCl3*OEt2 / CH2Cl2 / 1 h / -25 °C
8: NaH
9: 55 percent / n-BuLi / tetrahydrofuran / -75 - 0 °C
10: 69 percent / cerium(IV) ammonium nitrate / H2O; acetonitrile / 0.05 h / 0 °C
11: 88 percent / NaN3 / H2O; methanol / 1 h
12: 49 percent / Cu(acac)2 / benzene / 2 h / 80 °C
13: 1.) zinc powder, AcOH, 2.) K2CO3 / 1.) CH2Cl2, 2.) DMF, reflux 12 h
14: 76 percent / N-methylmorpholine oxide / OsO4 / H2O; 2-methyl-propan-2-ol / 12 h
15: Et3N / CH2Cl2 / 2 h / 0 °C
16: 56 percent / n-Bu4NN3 / benzene / 3 h / Heating
17: Et3N / CH2Cl2 / 2 h / 0 °C
18: tetrahydrofuran / 4 h / Heating
With
hydrogenchloride; copper acetylacetonate; potassium hydroxide; n-butyllithium; sodium azide; ammonium cerium(IV) nitrate; perchloryl fluoride; AlCl3 etherate; bromine; tetrabutylammoniun azide; sodium hydride; potassium carbonate; acetic acid; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc;
osmium(VIII) oxide;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol; benzene;
- Guidance literature:
-
Multi-step reaction with 19 steps
1: 82 percent / TiCl4
2: 80 percent / Br2
3: 1.) m-chloroperbenzoic acid, 2.) KOH / 2.) MeOH
4: NaH / dimethylformamide
5: n-BuLi, perchloryl fluoride / diethyl ether
6: HCl / acetone
7: 83 percent / K2CO3 / acetone
8: 62 percent / AlCl3*OEt2 / CH2Cl2 / 1 h / -25 °C
9: NaH
10: 55 percent / n-BuLi / tetrahydrofuran / -75 - 0 °C
11: 69 percent / cerium(IV) ammonium nitrate / H2O; acetonitrile / 0.05 h / 0 °C
12: 88 percent / NaN3 / H2O; methanol / 1 h
13: 49 percent / Cu(acac)2 / benzene / 2 h / 80 °C
14: 1.) zinc powder, AcOH, 2.) K2CO3 / 1.) CH2Cl2, 2.) DMF, reflux 12 h
15: 76 percent / N-methylmorpholine oxide / OsO4 / H2O; 2-methyl-propan-2-ol / 12 h
16: Et3N / CH2Cl2 / 2 h / 0 °C
17: 56 percent / n-Bu4NN3 / benzene / 3 h / Heating
18: Et3N / CH2Cl2 / 2 h / 0 °C
19: tetrahydrofuran / 4 h / Heating
With
hydrogenchloride; copper acetylacetonate; potassium hydroxide; n-butyllithium; sodium azide; ammonium cerium(IV) nitrate; perchloryl fluoride; AlCl3 etherate; bromine; tetrabutylammoniun azide; titanium tetrachloride; sodium hydride; potassium carbonate; acetic acid; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc;
osmium(VIII) oxide;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol; benzene;
