Technology Process of (1S,2R,3S,4R,5S,6R)-2-((2S,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,4,5,6-tetrakis-benzyloxy-cyclohexanol
There total 10 articles about (1S,2R,3S,4R,5S,6R)-2-((2S,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,4,5,6-tetrakis-benzyloxy-cyclohexanol which
guide to synthetic route it.
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synthetic route:
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637329-58-9
(1S,2R,3S,4R,5S,6R)-2-((2S,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,4,5,6-tetrakis-benzyloxy-cyclohexanol
- Guidance literature:
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With
sodium acetate; palladium dichloride;
In
acetic acid;
at 20 ℃;
for 6h;
DOI:10.1055/s-2003-40339
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-
637329-58-9
(1S,2R,3S,4R,5S,6R)-2-((2S,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,4,5,6-tetrakis-benzyloxy-cyclohexanol
- Guidance literature:
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Multi-step reaction with 10 steps
1: 56 percent / H2SO4 / dimethylsulfoxide / 55 °C
2: 100 percent / NaH / dimethylformamide / -20 °C
3: 80 percent / CH3COOH
4: 100 percent / pyridine / CH2Cl2 / -78 °C
5: 100 percent / DMAP; pyridine / 20 °C
6: 68 percent / H2O / dimethylformamide / 90 °C
7: 71 percent / dppb / Pd2(dba)3 / tetrahydrofuran / 70 °C
8: NaOMe / methanol; tetrahydrofuran
9: 42 percent / TMSOTf; 4 Angstroem molecular sieves / CH2Cl2 / 0.67 h / -25 - 20 °C
10: 62 percent / aq. AcONa; PdCl2 / acetic acid / 6 h / 20 °C
With
pyridine; dmap; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sulfuric acid; water; sodium methylate; sodium acetate; sodium hydride; acetic acid; 1,4-di(diphenylphosphino)-butane; palladium dichloride;
tris(dibenzylideneacetone)dipalladium (0);
In
tetrahydrofuran; methanol; dichloromethane; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1055/s-2003-40339
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-
637329-58-9
(1S,2R,3S,4R,5S,6R)-2-((2S,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,4,5,6-tetrakis-benzyloxy-cyclohexanol
- Guidance literature:
-
Multi-step reaction with 7 steps
1: 100 percent / pyridine / CH2Cl2 / -78 °C
2: 100 percent / DMAP; pyridine / 20 °C
3: 68 percent / H2O / dimethylformamide / 90 °C
4: 71 percent / dppb / Pd2(dba)3 / tetrahydrofuran / 70 °C
5: NaOMe / methanol; tetrahydrofuran
6: 42 percent / TMSOTf; 4 Angstroem molecular sieves / CH2Cl2 / 0.67 h / -25 - 20 °C
7: 62 percent / aq. AcONa; PdCl2 / acetic acid / 6 h / 20 °C
With
pyridine; dmap; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; water; sodium methylate; sodium acetate; 1,4-di(diphenylphosphino)-butane; palladium dichloride;
tris(dibenzylideneacetone)dipalladium (0);
In
tetrahydrofuran; methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide;
DOI:10.1055/s-2003-40339