Technology Process of (S)-11-((2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetradecanoic acid methyl ester
There total 18 articles about (S)-11-((2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetradecanoic acid methyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 14 steps
1.1: pyridine / CH2Cl2
2.1: tert-BuOK / tetrahydrofuran
3.1: CuI / tetrahydrofuran / 0 °C
4.1: pyridine
5.1: n-Bu4NF / tetrahydrofuran
6.1: CBr4; Ph3P / dimethylformamide
7.1: Bu3SnH; AIBN / toluene / 80 °C
8.1: NaOMe / methanol / 70 °C
9.1: Na; liq. NH3 / -80 °C
10.1: TEMPO; TBACl; NCS / CH2Cl2; H2O / pH 8.6
10.2: NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; various solvent(s); H2O
11.1: diethyl ether
12.1: NIS; TfOH; 4 Angstroem MS / CH2Cl2 / -20 °C
13.1: NaOMe / methanol
14.1: NaBH4 / dimethylformamide / 70 °C
With
pyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium tetrahydroborate; N-chloro-succinimide; N-iodo-succinimide; copper(l) iodide; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; trifluorormethanesulfonic acid; 4 Angstroem MS; potassium tert-butylate; tetrabutyl ammonium fluoride; tetrabutyl-ammonium chloride; ammonia; tri-n-butyl-tin hydride; sodium methylate; sodium; triphenylphosphine;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene;
1.1: Etherification / 2.1: Cyclization / 3.1: Grignard reaction / 4.1: Esterification / 5.1: Elimination / 6.1: Bromination / 7.1: Reduction / 8.1: Hydrolysis / 9.1: Birch reduction / 10.1: Oxidation / 10.2: Oxidation / 11.1: Esterification / 12.1: glycosylation / 13.1: Deacetylation / 14.1: Hydrogenolysis;
DOI:10.1016/S0040-4039(00)00427-5
- Guidance literature:
-
Multi-step reaction with 3 steps
1: NIS; TfOH; 4 Angstroem MS / CH2Cl2 / -20 °C
2: NaOMe / methanol
3: NaBH4 / dimethylformamide / 70 °C
With
sodium tetrahydroborate; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 Angstroem MS; sodium methylate;
In
methanol; dichloromethane; N,N-dimethyl-formamide;
1: glycosylation / 2: Deacetylation / 3: Hydrogenolysis;
DOI:10.1016/S0040-4039(00)00427-5
