Technology Process of Acetic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-hydroxymethyl-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-tetrahydro-pyran-3-yl ester
There total 19 articles about Acetic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-hydroxymethyl-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-tetrahydro-pyran-3-yl ester which
guide to synthetic route it.
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synthetic route:
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1053613-29-8
Acetic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-hydroxymethyl-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-tetrahydro-pyran-3-yl ester
- Guidance literature:
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Multi-step reaction with 13 steps
2: 3-Angstroem molecular sieves, NaHCO3, Dess-Martin periodinane / CH2Cl2 / 1.5 h
3: 0.02percent NiCl2 in CrCl2 / tetrahydrofuran; dimethylformamide / 12 h / Ambient temperature
4: 89 percent / H2 / 10percent Pd-Pb/CaCO3 / methanol / 12 h / 760 Torr / Ambient temperature
5: 88 percent / NaH, imidazole, (n-Bu)4NI / tetrahydrofuran; dimethylformamide / 1.) room temp., 15 min, 2.) 6 h
6: 91 percent / OsO4 / tetrahydrofuran; pyridine; toluene / 48 h / -35 °C
7: 1.) Bu2SnO, 2.) CsF, (n-Bu)4NI / 1.) toluene, reflux, 2 h, 2.) DMF, room temp., 36 h
8: 95 percent / pyridine, 4-(dimethylamino)pyridine / 0.5 h
9: 95 percent / 80percent aq. AcOH / 12 h / Ambient temperature
10: pyridine / 9 h
11: NaH, imidazole / tetrahydrofuran / 0.33 h / 0 °C
12: DDQ / CH2Cl2 / 2 h / 0 °C / pH 7 phosphate buffer
13: p-TsOH*H2O / CH2Cl2 / 0.83 h
With
pyridine; 1H-imidazole; dmap; osmium(VIII) oxide; 3 A molecular sieve; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; cesium fluoride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel dichloride;
Lindlar's catalyst; palladium-lead;
In
tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00080a016
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1053613-29-8
Acetic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-hydroxymethyl-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-tetrahydro-pyran-3-yl ester
- Guidance literature:
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Multi-step reaction with 12 steps
1: 3-Angstroem molecular sieves, NaHCO3, Dess-Martin periodinane / CH2Cl2 / 1.5 h
2: 0.02percent NiCl2 in CrCl2 / tetrahydrofuran; dimethylformamide / 12 h / Ambient temperature
3: 89 percent / H2 / 10percent Pd-Pb/CaCO3 / methanol / 12 h / 760 Torr / Ambient temperature
4: 88 percent / NaH, imidazole, (n-Bu)4NI / tetrahydrofuran; dimethylformamide / 1.) room temp., 15 min, 2.) 6 h
5: 91 percent / OsO4 / tetrahydrofuran; pyridine; toluene / 48 h / -35 °C
6: 1.) Bu2SnO, 2.) CsF, (n-Bu)4NI / 1.) toluene, reflux, 2 h, 2.) DMF, room temp., 36 h
7: 95 percent / pyridine, 4-(dimethylamino)pyridine / 0.5 h
8: 95 percent / 80percent aq. AcOH / 12 h / Ambient temperature
9: pyridine / 9 h
10: NaH, imidazole / tetrahydrofuran / 0.33 h / 0 °C
11: DDQ / CH2Cl2 / 2 h / 0 °C / pH 7 phosphate buffer
12: p-TsOH*H2O / CH2Cl2 / 0.83 h
With
pyridine; 1H-imidazole; dmap; osmium(VIII) oxide; 3 A molecular sieve; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; cesium fluoride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel dichloride;
Lindlar's catalyst; palladium-lead;
In
tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00080a016
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1053613-29-8
Acetic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-hydroxymethyl-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-tetrahydro-pyran-3-yl ester
- Guidance literature:
-
Multi-step reaction with 11 steps
1: 0.02percent NiCl2 in CrCl2 / tetrahydrofuran; dimethylformamide / 12 h / Ambient temperature
2: 89 percent / H2 / 10percent Pd-Pb/CaCO3 / methanol / 12 h / 760 Torr / Ambient temperature
3: 88 percent / NaH, imidazole, (n-Bu)4NI / tetrahydrofuran; dimethylformamide / 1.) room temp., 15 min, 2.) 6 h
4: 91 percent / OsO4 / tetrahydrofuran; pyridine; toluene / 48 h / -35 °C
5: 1.) Bu2SnO, 2.) CsF, (n-Bu)4NI / 1.) toluene, reflux, 2 h, 2.) DMF, room temp., 36 h
6: 95 percent / pyridine, 4-(dimethylamino)pyridine / 0.5 h
7: 95 percent / 80percent aq. AcOH / 12 h / Ambient temperature
8: pyridine / 9 h
9: NaH, imidazole / tetrahydrofuran / 0.33 h / 0 °C
10: DDQ / CH2Cl2 / 2 h / 0 °C / pH 7 phosphate buffer
11: p-TsOH*H2O / CH2Cl2 / 0.83 h
With
pyridine; 1H-imidazole; dmap; osmium(VIII) oxide; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; acetic acid; cesium fluoride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel dichloride;
Lindlar's catalyst; palladium-lead;
In
tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00080a016
