Technology Process of Methanesulfonic acid (2S,3S)-3-[(1R,2R,3S,5R,6S,7S)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-7-((2S,3S)-3-methanesulfonyloxymethyl-oxiranyl)-2,6-bis-(4-methoxy-benzyloxy)-1-methyl-octyl]-oxiranylmethyl ester
There total 11 articles about Methanesulfonic acid (2S,3S)-3-[(1R,2R,3S,5R,6S,7S)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-7-((2S,3S)-3-methanesulfonyloxymethyl-oxiranyl)-2,6-bis-(4-methoxy-benzyloxy)-1-methyl-octyl]-oxiranylmethyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
triethylamine;
In
dichloromethane;
at 20 ℃;
for 1h;
DOI:10.1021/ol0473400
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: KHMDS; 18-C-6 / tetrahydrofuran / 0.25 h / -78 °C
1.2: 6.3 g / tetrahydrofuran / -78 - 20 °C
2.1: 100 percent / DIBAL / CH2Cl2; hexane / 1 h / -78 °C
3.1: BH3*THF / tetrahydrofuran / 0.75 h
3.2: 70 percent / NaBO3*H2O / tetrahydrofuran; H2O / 1 h / 20 °C
4.1: PPTS / CH2Cl2 / 20 °C
5.1: 2.03 g / DIBAL / toluene / -78 - 0 °C
6.1: 97 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / 0.5 h / -78 - 20 °C
7.1: NaH / tetrahydrofuran / -78 °C
7.2: 96 percent / tetrahydrofuran / -78 - 20 °C
8.1: 97 percent / DIBAL / CH2Cl2; hexane / 1 h / -78 °C
9.1: 68 percent / Ti(OiPr)4; L-(+)-DET; tert-butyl hydroperoxide / CH2Cl2; decane / -20 °C
10.1: 94 percent / Et3N / CH2Cl2 / 1 h / 20 °C
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; borane-THF; oxalyl dichloride; 18-crown-6 ether; diethyl (2R,3R)-tartrate; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; decane; hexane; dichloromethane; toluene;
6.1: Swern oxidation / 7.2: Horner-Wadsworth-Emmons reaction / 9.1: Sharpless asymmetric epoxidation;
DOI:10.1021/ol0473400
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: BH3*THF / tetrahydrofuran / 0.75 h
1.2: 70 percent / NaBO3*H2O / tetrahydrofuran; H2O / 1 h / 20 °C
2.1: PPTS / CH2Cl2 / 20 °C
3.1: 2.03 g / DIBAL / toluene / -78 - 0 °C
4.1: 97 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / 0.5 h / -78 - 20 °C
5.1: NaH / tetrahydrofuran / -78 °C
5.2: 96 percent / tetrahydrofuran / -78 - 20 °C
6.1: 97 percent / DIBAL / CH2Cl2; hexane / 1 h / -78 °C
7.1: 68 percent / Ti(OiPr)4; L-(+)-DET; tert-butyl hydroperoxide / CH2Cl2; decane / -20 °C
8.1: 94 percent / Et3N / CH2Cl2 / 1 h / 20 °C
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; borane-THF; oxalyl dichloride; diethyl (2R,3R)-tartrate; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; decane; hexane; dichloromethane; toluene;
4.1: Swern oxidation / 5.2: Horner-Wadsworth-Emmons reaction / 7.1: Sharpless asymmetric epoxidation;
DOI:10.1021/ol0473400
![{(2S,3S)-3-[(1R,2R,3S,5R,6S,7S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-((2S,3S)-3-hydroxymethyl-oxiranyl)-2,6-bis-(4-methoxy-benzyloxy)-1-methyl-octyl]-oxiranyl}-methanol](/Databaselist/images/loading.webp)
