Technology Process of (2R,3S,1'R)-N-benzoxycarbonyl-2-(1',4'-dihydroxy-2'butenyl)-3-methoxymethyloxypyrrolidine
There total 10 articles about (2R,3S,1'R)-N-benzoxycarbonyl-2-(1',4'-dihydroxy-2'butenyl)-3-methoxymethyloxypyrrolidine which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
phosphorous acid trimethyl ester;
In
methanol;
at 60 ℃;
for 2h;
DOI:10.1139/v00-043
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: 80 percent / acetonitrile / 1 h / 0 °C
2.1: t-BuOK / toluene / 0.5 h / 0 °C
3.1: 45 percent / sucrose; baker's yeast / H2O / 48 h / 40 °C
4.1: 92 percent / diisopropylethylamine / CH2Cl2 / 24 h / 20 °C
5.1: 72 percent / LiBH4 / diethyl ether / 4 h / 0 °C
6.1: 98 percent / oxalyl chloride; DMSO / CH2Cl2 / 1 h / -78 °C
7.1: n-BuLi / tetrahydrofuran; pentane / 0.5 h / 0 °C
7.2: 72 percent / titanium(IV)isopropoxide / tetrahydrofuran; pentane / 0.5 h / 0 °C
8.1: MCPBA / CH2Cl2 / 1 h / 0 °C
9.1: trimethyl phosphite / methanol / 2 h / 60 °C
With
lithium borohydride; n-butyllithium; baker's yeast; oxalyl dichloride; potassium tert-butylate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; Sucrose; phosphorous acid trimethyl ester;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; acetonitrile; pentane;
1.1: Condensation / 2.1: Dickemann cyclization / 3.1: Reduction / 4.1: Etherification / 5.1: Reduction / 6.1: Oxidation / 7.1: Metallation / 7.2: Substitution / 8.1: Oxidation / 9.1: Elimination;
DOI:10.1139/v00-043
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: t-BuOK / toluene / 0.5 h / 0 °C
2.1: 45 percent / sucrose; baker's yeast / H2O / 48 h / 40 °C
3.1: 92 percent / diisopropylethylamine / CH2Cl2 / 24 h / 20 °C
4.1: 72 percent / LiBH4 / diethyl ether / 4 h / 0 °C
5.1: 98 percent / oxalyl chloride; DMSO / CH2Cl2 / 1 h / -78 °C
6.1: n-BuLi / tetrahydrofuran; pentane / 0.5 h / 0 °C
6.2: 72 percent / titanium(IV)isopropoxide / tetrahydrofuran; pentane / 0.5 h / 0 °C
7.1: MCPBA / CH2Cl2 / 1 h / 0 °C
8.1: trimethyl phosphite / methanol / 2 h / 60 °C
With
lithium borohydride; n-butyllithium; baker's yeast; oxalyl dichloride; potassium tert-butylate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; Sucrose; phosphorous acid trimethyl ester;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; pentane;
1.1: Dickemann cyclization / 2.1: Reduction / 3.1: Etherification / 4.1: Reduction / 5.1: Oxidation / 6.1: Metallation / 6.2: Substitution / 7.1: Oxidation / 8.1: Elimination;
DOI:10.1139/v00-043
