Technology Process of N-[(2R,3R,4R,5S,6R)-2-Allyloxy-4-benzyloxy-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-6-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl]-acetamide
There total 8 articles about N-[(2R,3R,4R,5S,6R)-2-Allyloxy-4-benzyloxy-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-6-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl]-acetamide which
guide to synthetic route it.
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synthetic route:
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131204-14-3
N-[(2R,3R,4R,5S,6R)-2-Allyloxy-4-benzyloxy-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-6-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl]-acetamide
- Guidance literature:
-
With
sodium methylate;
In
methanol;
for 24h;
Ambient temperature;
DOI:10.1016/0008-6215(90)80134-O
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131204-14-3
N-[(2R,3R,4R,5S,6R)-2-Allyloxy-4-benzyloxy-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-6-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl]-acetamide
- Guidance literature:
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Multi-step reaction with 8 steps
1: 92.2 percent / p-toluenesulfonic acid / dimethylformamide / 24 h / Ambient temperature
2: 98.5 percent / barium oxide, barium hydroxide octahydrate / dimethylformamide / 12 h / Ambient temperature
3: 97.2 percent / pyridinium p-toluenesulfonate / methanol / 0.17 h / Heating
4: 1) dibutyltin oxide, 2) tetrabutylammonium iodide / 1) benzene, 3 h, reflux, 2) 45-50 deg C, 6 h
5: 64.7 percent / 4 Angstroem molecular sieves / mercury(II) cyanide / nitromethane; toluene / 4 h / Ambient temperature
6: 83.8 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2; H2O / 3 h / Ambient temperature
7: 38.7 percent / 4 Angstroem molecular sieves, trimethylsilyl trifluoromethanesulfonate / CH2Cl2 / 24 h
8: 93 percent / sodium methoxide / methanol / 24 h / Ambient temperature
With
barium hydroxide octahydrate; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium methylate; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; toluene-4-sulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; barium(II) oxide;
mercury(II) cyanide;
In
methanol; nitromethane; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1016/0008-6215(90)80134-O
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131204-14-3
N-[(2R,3R,4R,5S,6R)-2-Allyloxy-4-benzyloxy-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-6-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl]-acetamide
- Guidance literature:
-
Multi-step reaction with 6 steps
1: 97.2 percent / pyridinium p-toluenesulfonate / methanol / 0.17 h / Heating
2: 1) dibutyltin oxide, 2) tetrabutylammonium iodide / 1) benzene, 3 h, reflux, 2) 45-50 deg C, 6 h
3: 64.7 percent / 4 Angstroem molecular sieves / mercury(II) cyanide / nitromethane; toluene / 4 h / Ambient temperature
4: 83.8 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2; H2O / 3 h / Ambient temperature
5: 38.7 percent / 4 Angstroem molecular sieves, trimethylsilyl trifluoromethanesulfonate / CH2Cl2 / 24 h
6: 93 percent / sodium methoxide / methanol / 24 h / Ambient temperature
With
trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium methylate; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
mercury(II) cyanide;
In
methanol; nitromethane; dichloromethane; water; toluene;
DOI:10.1016/0008-6215(90)80134-O