Technology Process of Benzoic acid (2S,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-2-((S)-1,2-dihydroxy-ethyl)-6-furan-2-yl-6-methoxy-tetrahydro-pyran-3-yl ester
There total 11 articles about Benzoic acid (2S,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-2-((S)-1,2-dihydroxy-ethyl)-6-furan-2-yl-6-methoxy-tetrahydro-pyran-3-yl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 8 steps
1: 3.6 g / diethyl ether / 1 h / 0 °C
2: triethylamine / diethyl ether / 1.) 0 gradC, 5 min; 2.) roomtemp., 30 min
3: 1.) Dibal; 2.) DMF; 3.) BF3*OEt2; 4.) trifluoroacetic acid
4: ceric chloride heptahydrate, NaBH4 / CH2Cl2; ethanol / 1 h / -78 °C
5: 90 percent / CSA / methanol; benzene / 3 h / 25 °C
6: 93 percent / 2,6-lutidine / CH2Cl2 / 1 h / -78 °C
7: 96 percent / H2O2, pyridine / tetrahydrofuran / 4 h / Ambient temperature
8: 1.) osmium tetraoxide, NMO; 2.) Florisil, NaHSO3 / 1.) THF-water, 2 h; 2.) THF-water, roomtemp., 1 h
With
pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; florisil; osmium(VIII) oxide; N-methyl-2-indolinone; ceric chloride heptahydrate; boron trifluoride diethyl etherate; dihydrogen peroxide; diisobutylaluminium hydride; sodium hydrogensulfite; triethylamine; N,N-dimethyl-formamide; trifluoroacetic acid;
camphor-10-sulfonic acid;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; benzene;
DOI:10.1021/ja00220a035
- Guidance literature:
-
Multi-step reaction with 7 steps
1: triethylamine / diethyl ether / 1.) 0 gradC, 5 min; 2.) roomtemp., 30 min
2: 1.) Dibal; 2.) DMF; 3.) BF3*OEt2; 4.) trifluoroacetic acid
3: ceric chloride heptahydrate, NaBH4 / CH2Cl2; ethanol / 1 h / -78 °C
4: 90 percent / CSA / methanol; benzene / 3 h / 25 °C
5: 93 percent / 2,6-lutidine / CH2Cl2 / 1 h / -78 °C
6: 96 percent / H2O2, pyridine / tetrahydrofuran / 4 h / Ambient temperature
7: 1.) osmium tetraoxide, NMO; 2.) Florisil, NaHSO3 / 1.) THF-water, 2 h; 2.) THF-water, roomtemp., 1 h
With
pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; florisil; osmium(VIII) oxide; N-methyl-2-indolinone; ceric chloride heptahydrate; boron trifluoride diethyl etherate; dihydrogen peroxide; diisobutylaluminium hydride; sodium hydrogensulfite; triethylamine; N,N-dimethyl-formamide; trifluoroacetic acid;
camphor-10-sulfonic acid;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; benzene;
DOI:10.1021/ja00220a035
- Guidance literature:
-
Multi-step reaction with 6 steps
1: 1.) Dibal; 2.) DMF; 3.) BF3*OEt2; 4.) trifluoroacetic acid
2: ceric chloride heptahydrate, NaBH4 / CH2Cl2; ethanol / 1 h / -78 °C
3: 90 percent / CSA / methanol; benzene / 3 h / 25 °C
4: 93 percent / 2,6-lutidine / CH2Cl2 / 1 h / -78 °C
5: 96 percent / H2O2, pyridine / tetrahydrofuran / 4 h / Ambient temperature
6: 1.) osmium tetraoxide, NMO; 2.) Florisil, NaHSO3 / 1.) THF-water, 2 h; 2.) THF-water, roomtemp., 1 h
With
pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; florisil; osmium(VIII) oxide; N-methyl-2-indolinone; ceric chloride heptahydrate; boron trifluoride diethyl etherate; dihydrogen peroxide; diisobutylaluminium hydride; sodium hydrogensulfite; N,N-dimethyl-formamide; trifluoroacetic acid;
camphor-10-sulfonic acid;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; benzene;
DOI:10.1021/ja00220a035
