Technology Process of Methanesulfonic acid (2S,3S)-3-benzyloxy-2-[(R)-1-((R)-1-benzyloxy-2-methanesulfonyloxy-ethyl)-but-3-enyloxy]-hex-5-enyl ester
There total 13 articles about Methanesulfonic acid (2S,3S)-3-benzyloxy-2-[(R)-1-((R)-1-benzyloxy-2-methanesulfonyloxy-ethyl)-but-3-enyloxy]-hex-5-enyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
triethylamine;
In
dichloromethane;
at 0 - 25 ℃;
for 3.5h;
DOI:10.1055/s-2002-33511
- Guidance literature:
-
Multi-step reaction with 12 steps
1: 89 percent / MeONa / methanol / 48 h / 0 °C
2: imidazole / dimethylformamide / 0.5 h / 24 °C
3: CSA / 1.5 h / 24 °C
4: 99 percent / NaI; Bu4NI / tetrahydrofuran / 30 h / 24 °C
5: 100 percent / TBAF / tetrahydrofuran / 2 h / 23 °C
6: (COCl)2; DMSO; Et3N / CH2Cl2 / 0.42 h / -78 - 0 °C
7: LiClO4 / diethyl ether / 23 h / 23 °C
8: 100 percent / NaH; Bu4NI / tetrahydrofuran / 22 h / 25 °C
9: 94 percent / aq. HCl / tetrahydrofuran / 3.5 h / 23 °C
10: aq. NaIO4 / methanol / 1.3 h / 23 °C / pH 7
11: NaBH4 / methanol / 2 h / 0 - 23 °C
12: 100 percent / Et3N / CH2Cl2 / 3.5 h / 0 - 25 °C
With
1H-imidazole; hydrogenchloride; sodium tetrahydroborate; sodium periodate; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium methylate; lithium perchlorate; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; sodium iodide;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
6: Swern oxidation;
DOI:10.1055/s-2002-33511
- Guidance literature:
-
Multi-step reaction with 11 steps
1: imidazole / dimethylformamide / 0.5 h / 24 °C
2: CSA / 1.5 h / 24 °C
3: 99 percent / NaI; Bu4NI / tetrahydrofuran / 30 h / 24 °C
4: 100 percent / TBAF / tetrahydrofuran / 2 h / 23 °C
5: (COCl)2; DMSO; Et3N / CH2Cl2 / 0.42 h / -78 - 0 °C
6: LiClO4 / diethyl ether / 23 h / 23 °C
7: 100 percent / NaH; Bu4NI / tetrahydrofuran / 22 h / 25 °C
8: 94 percent / aq. HCl / tetrahydrofuran / 3.5 h / 23 °C
9: aq. NaIO4 / methanol / 1.3 h / 23 °C / pH 7
10: NaBH4 / methanol / 2 h / 0 - 23 °C
11: 100 percent / Et3N / CH2Cl2 / 3.5 h / 0 - 25 °C
With
1H-imidazole; hydrogenchloride; sodium tetrahydroborate; sodium periodate; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; lithium perchlorate; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; sodium iodide;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
5: Swern oxidation;
DOI:10.1055/s-2002-33511
