Technology Process of (3S,4S,5R)-4,5-Bis-benzyloxy-1-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-(4-methoxy-benzyloxy)-pentan-2-one
There total 15 articles about (3S,4S,5R)-4,5-Bis-benzyloxy-1-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-(4-methoxy-benzyloxy)-pentan-2-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 7 steps
1: 95 percent / Et3N / diethyl ether / 0 °C
2: 94 percent / NaI, NaHCO3 / acetone
3: 95 percent / dimethylformamide / 110 °C
4: 1) n-BuLi / 1) THF, 0 deg C
5: 75 percent / N,N'-bis(mesitylmethyl)-(R,R')-1,2-diphenyl-1,2-diaminoethane / OsO4 / CH2Cl2 / -80 °C
6: 1) NaH / 1) THF, 0 deg C
7: 1) (COCl)2, DMSO, 2) Et3N
With
n-butyllithium; oxalyl dichloride; 1,2-diphenyl-N,N'-bis[(2,4,6-trimethylphenyl)methyl]-1,2-diaminoethane; sodium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; sodium iodide;
osmium(VIII) oxide;
In
diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo00028a017
- Guidance literature:
-
Multi-step reaction with 4 steps
1: 1) n-BuLi / 1) THF, 0 deg C
2: 75 percent / N,N'-bis(mesitylmethyl)-(R,R')-1,2-diphenyl-1,2-diaminoethane / OsO4 / CH2Cl2 / -80 °C
3: 1) NaH / 1) THF, 0 deg C
4: 1) (COCl)2, DMSO, 2) Et3N
With
n-butyllithium; oxalyl dichloride; 1,2-diphenyl-N,N'-bis[(2,4,6-trimethylphenyl)methyl]-1,2-diaminoethane; sodium hydride; dimethyl sulfoxide; triethylamine;
osmium(VIII) oxide;
In
dichloromethane;
DOI:10.1021/jo00028a017
- Guidance literature:
-
Multi-step reaction with 5 steps
1: 1) (COCl)2, DMSO, 2) Et3N
2: 1) n-BuLi / 1) THF, 0 deg C
3: 75 percent / N,N'-bis(mesitylmethyl)-(R,R')-1,2-diphenyl-1,2-diaminoethane / OsO4 / CH2Cl2 / -80 °C
4: 1) NaH / 1) THF, 0 deg C
5: 1) (COCl)2, DMSO, 2) Et3N
With
n-butyllithium; oxalyl dichloride; 1,2-diphenyl-N,N'-bis[(2,4,6-trimethylphenyl)methyl]-1,2-diaminoethane; sodium hydride; dimethyl sulfoxide; triethylamine;
osmium(VIII) oxide;
In
dichloromethane;
DOI:10.1021/jo00028a017