Technology Process of 2-(4-methoxybenzyloxy)ethyl 2-deoxy-4,6-O-isopropylidene-3-O-[(R)-3-[(Z)-tetradec-7-enyloxy]tetradecyl]-2-trifluoroacetamido-α-D-glycopyranoside
There total 11 articles about 2-(4-methoxybenzyloxy)ethyl 2-deoxy-4,6-O-isopropylidene-3-O-[(R)-3-[(Z)-tetradec-7-enyloxy]tetradecyl]-2-trifluoroacetamido-α-D-glycopyranoside which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
2-(4-methoxybenzyloxy)ethyl 2-deoxy-4,6-O-isopropylidene-2-trifluoroacetamido-α-D-glycopyranoside;
With
sodium hydride;
In
N,N-dimethyl-formamide;
at 0 ℃;
for 0.25h;
1-methylsulfonyloxy-3-[(R)-[(Z)-tetradec-7-enyloxy]]tetradecane;
In
N,N-dimethyl-formamide;
at 20 ℃;
for 3h;
DOI:10.1246/bcsj.76.1011
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: 47.7 g / D-10-camphorsulfonic acid / methanol / 24 h / 20 °C
2.1: H2 / Lindlar's catalyst / hexane / 9 h / 20 °C
3.1: 8.7 g / (COCl)2; DMSO; Et3N / CH2Cl2 / 1 h / 0 °C
4.1: 100 percent / D-10-camphorsulfonic acid / benzene / 2 h / 50 °C / 70 Torr
5.1: 81 percent / DIBAL / toluene / 10 h / 50 °C
6.1: 100 percent / N,N-diisopropylethylamine / CH2Cl2 / 4 h / 20 °C
7.1: NaH / dimethylformamide / 0.25 h / 0 °C
7.2: 85 percent / dimethylformamide / 3 h / 20 °C
With
oxalyl dichloride; camphor-10-sulfonic acid; hydrogen; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine;
Lindlar's catalyst;
In
methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1246/bcsj.76.1011
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / 0 °C
1.2: hexamethylphosphoric triamide (HMPA) / tetrahydrofuran; hexane / 22 h / 20 °C
2.1: 47.7 g / D-10-camphorsulfonic acid / methanol / 24 h / 20 °C
3.1: H2 / Lindlar's catalyst / hexane / 9 h / 20 °C
4.1: 8.7 g / (COCl)2; DMSO; Et3N / CH2Cl2 / 1 h / 0 °C
5.1: 100 percent / D-10-camphorsulfonic acid / benzene / 2 h / 50 °C / 70 Torr
6.1: 81 percent / DIBAL / toluene / 10 h / 50 °C
7.1: 100 percent / N,N-diisopropylethylamine / CH2Cl2 / 4 h / 20 °C
8.1: NaH / dimethylformamide / 0.25 h / 0 °C
8.2: 85 percent / dimethylformamide / 3 h / 20 °C
With
n-butyllithium; oxalyl dichloride; camphor-10-sulfonic acid; hydrogen; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine;
Lindlar's catalyst;
In
tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1246/bcsj.76.1011
