Technology Process of (3R,4R,5R)-4,5-Diacetoxy-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-cyclohex-1-enecarboxylic acid methyl ester
There total 7 articles about (3R,4R,5R)-4,5-Diacetoxy-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-cyclohex-1-enecarboxylic acid methyl ester which
guide to synthetic route it.
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synthetic route:
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(1R,2R,3R,4R,5R)-4,5-Diacetoxy-2-chlorocarbonyl-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexanecarboxylic acid methyl ester
- Guidance literature:
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(1R,2R,3R,4R,5R)-4,5-Diacetoxy-2-chlorocarbonyl-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexanecarboxylic acid methyl ester;
With
Bromotrichloromethane; 2-mercaptopyridine-1-oxide sodium salt;
2,2'-azobis(isobutyronitrile);
at 100 ℃;
for 3.5h;
With
2,6-dichloro-benzonitrile;
In
dichloromethane;
for 24h;
Heating;
DOI:10.1016/S0040-4039(00)00225-2
- Guidance literature:
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Multi-step reaction with 7 steps
1.1: dimethylsulfoxide / 18 h / 20 °C
1.2: 64 percent / OsO4; NMO / acetone; H2O / 0.5 h / -10 °C
2.1: 84 percent / HClO4 / 2 h
3.1: 83 percent / Et3N; DMAP / CH2Cl2 / 2 h
4.1: diethyl ether; CH2Cl2
5.1: H2 / Pd-C / CH2Cl2 / 4 h
6.1: (COCl)2; DMF / CH2Cl2 / 1 h
7.1: 2-mercaptopyridine N-oxide Na salt; BrCCl3 / AIBN / 3.5 h / 100 °C
7.2: 53 percent / DBN / CH2Cl2 / 24 h / Heating
With
dmap; perchloric acid; oxalyl dichloride; Bromotrichloromethane; hydrogen; 2-mercaptopyridine-1-oxide sodium salt; triethylamine; N,N-dimethyl-formamide;
palladium on activated charcoal; 2,2'-azobis(isobutyronitrile);
In
diethyl ether; dichloromethane; dimethyl sulfoxide;
1.1: Diels-Alder reaction / 1.2: Upjohn dihydroxilation / 2.1: Acetylation / 3.1: alcoholysis / 4.1: Esterification / 5.1: Catalytic hydrogenation / 6.1: Chlorination / 7.1: Hunsdiecker-Barton reaction / 7.2: Dehydrobromination;
DOI:10.1016/S0040-4039(00)00225-2
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273728-83-9
Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((3aR,4R,5R,6R,7aR)-5,6-dihydroxy-1,3-dioxo-octahydro-isobenzofuran-4-yloxy)-tetrahydro-pyran-3-yl ester
- Guidance literature:
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Multi-step reaction with 6 steps
1.1: 84 percent / HClO4 / 2 h
2.1: 83 percent / Et3N; DMAP / CH2Cl2 / 2 h
3.1: diethyl ether; CH2Cl2
4.1: H2 / Pd-C / CH2Cl2 / 4 h
5.1: (COCl)2; DMF / CH2Cl2 / 1 h
6.1: 2-mercaptopyridine N-oxide Na salt; BrCCl3 / AIBN / 3.5 h / 100 °C
6.2: 53 percent / DBN / CH2Cl2 / 24 h / Heating
With
dmap; perchloric acid; oxalyl dichloride; Bromotrichloromethane; hydrogen; 2-mercaptopyridine-1-oxide sodium salt; triethylamine; N,N-dimethyl-formamide;
palladium on activated charcoal; 2,2'-azobis(isobutyronitrile);
In
diethyl ether; dichloromethane;
1.1: Acetylation / 2.1: alcoholysis / 3.1: Esterification / 4.1: Catalytic hydrogenation / 5.1: Chlorination / 6.1: Hunsdiecker-Barton reaction / 6.2: Dehydrobromination;
DOI:10.1016/S0040-4039(00)00225-2