Technology Process of Acetic acid (1R,2R,3R,4S,5S,6R)-6-azidocarbonyl-3,4,5-tris-benzyloxy-bicyclo[3.1.0]hex-2-ylmethyl ester
There total 9 articles about Acetic acid (1R,2R,3R,4S,5S,6R)-6-azidocarbonyl-3,4,5-tris-benzyloxy-bicyclo[3.1.0]hex-2-ylmethyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
7-O-acetyl-3,4,5-tri-O-benzyl-2,6-dideoxy-2,6-methylene-D-glycero-D-gulo-3,6a-cycloheptonic acid;
With
chloroformic acid ethyl ester; triethylamine;
In
acetone;
at 0 ℃;
for 1h;
With
sodium azide;
In
water; acetone;
at 0 - 23 ℃;
for 2.5h;
DOI:10.1002/1522-2675(200204)85:4<1118::AID-HLCA1118>3.0.CO;2-S
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: 9.47 g / NaBH4; NiCl2 / methanol / 5 h / 20 °C
2.1: AcOH / CH2Cl2
2.2: 10.07 g / NaBH3CN / CH2Cl2 / 4 h / 0 - 20 °C
3.1: 11.48 g / imidazole / dimethylformamide / 3 h / 20 °C
4.1: 83 percent / MCPBA / CH2Cl2 / 0.25 h / 0 - 20 °C
5.1: 63 percent / 0.25 h / 145 °C
6.1: Cu powder / toluene / 10 h / 110 °C
7.1: 865 mg / KOH / ethanol; H2O / 15 h / 100 °C
8.1: 963 mg / pyridine / 4 h / 20 °C
9.1: Et3N; ethyl chloroformate / acetone / 1 h / 0 °C
9.2: 805 mg / NaN3 / acetone; H2O / 2.5 h / 0 - 23 °C
With
pyridine; 1H-imidazole; potassium hydroxide; sodium tetrahydroborate; chloroformic acid ethyl ester; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; nickel dichloride;
copper;
In
methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;
5.1: Cope elimination;
DOI:10.1002/1522-2675(200204)85:4<1118::AID-HLCA1118>3.0.CO;2-S
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: 11.48 g / imidazole / dimethylformamide / 3 h / 20 °C
2.1: 83 percent / MCPBA / CH2Cl2 / 0.25 h / 0 - 20 °C
3.1: 63 percent / 0.25 h / 145 °C
4.1: Cu powder / toluene / 10 h / 110 °C
5.1: 865 mg / KOH / ethanol; H2O / 15 h / 100 °C
6.1: 963 mg / pyridine / 4 h / 20 °C
7.1: Et3N; ethyl chloroformate / acetone / 1 h / 0 °C
7.2: 805 mg / NaN3 / acetone; H2O / 2.5 h / 0 - 23 °C
With
pyridine; 1H-imidazole; potassium hydroxide; chloroformic acid ethyl ester; triethylamine; 3-chloro-benzenecarboperoxoic acid;
copper;
In
ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;
3.1: Cope elimination;
DOI:10.1002/1522-2675(200204)85:4<1118::AID-HLCA1118>3.0.CO;2-S
