Technology Process of methyl (2R,3S,4S,5R)-5-[(3,4-dimethoxybenzyl)oxy]-3-methoxy-4-methyl-2-[(tert-butyldimethylsilyl)oxy]heptanoate
There total 11 articles about methyl (2R,3S,4S,5R)-5-[(3,4-dimethoxybenzyl)oxy]-3-methoxy-4-methyl-2-[(tert-butyldimethylsilyl)oxy]heptanoate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: 99 percent / H2; Amberlyst 15 / (R)-Binap-Ru(II)Cl2 / methanol / 100 °C / 3102.97 Torr
2.1: LDA / tetrahydrofuran / -78 °C
2.2: HMPA
3.1: LAH / diethyl ether / 0 °C
4.1: TsOH / benzene / Heating
5.1: DIBAL-H / CH2Cl2 / -78 °C
6.1: (COCl)2; DMSO; Et3N / CH2Cl2 / -78 °C
7.1: 75 percent / BF3*OEt2 / CH2Cl2 / -78 °C
8.1: 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 23 °C
9.1: OsO4; NMO / tetrahydrofuran; acetone; H2O
9.2: Pb(OAc)4 / ethyl acetate
10.1: sodium chlorite / CH2Cl2 / 0 °C / pH 7
With
sodium chlorite; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; 2,6-di-tert-butyl-4-methylpyridine; Amberlyst 15; oxalyl dichloride; boron trifluoride diethyl etherate; hydrogen; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide;
RuCl2[(R)-BINAP];
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone; benzene;
2.2: Frater-Seebach alkylation / 6.1: Swern oxidation;
DOI:10.1021/ol0272343
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: LAH / diethyl ether / 0 °C
2.1: TsOH / benzene / Heating
3.1: DIBAL-H / CH2Cl2 / -78 °C
4.1: (COCl)2; DMSO; Et3N / CH2Cl2 / -78 °C
5.1: 75 percent / BF3*OEt2 / CH2Cl2 / -78 °C
6.1: 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 23 °C
7.1: OsO4; NMO / tetrahydrofuran; acetone; H2O
7.2: Pb(OAc)4 / ethyl acetate
8.1: sodium chlorite / CH2Cl2 / 0 °C / pH 7
With
sodium chlorite; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; 2,6-di-tert-butyl-4-methylpyridine; oxalyl dichloride; boron trifluoride diethyl etherate; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; acetone; benzene;
4.1: Swern oxidation;
DOI:10.1021/ol0272343
