Technology Process of (2R)-2-[(5S)-6-[(2S,3S,4S,6R)-6-[(3S,5S,7R,10S,12R,15R)-3-[(5R,6S)-5-ethyl-5-hydroxy-6-methyloxan-2-yl]-15-hydroxy-3,10,12-trimethyl-4,6,8-trioxadispiro[4.1.57.35]pentadec-13-en-9-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-5-methyloxan-2-yl]butanoic acid
There total 132 articles about (2R)-2-[(5S)-6-[(2S,3S,4S,6R)-6-[(3S,5S,7R,10S,12R,15R)-3-[(5R,6S)-5-ethyl-5-hydroxy-6-methyloxan-2-yl]-15-hydroxy-3,10,12-trimethyl-4,6,8-trioxadispiro[4.1.57.35]pentadec-13-en-9-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-5-methyloxan-2-yl]butanoic acid which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
3 A molecular sieve; trifluoroacetic acid;
In
dichloromethane;
for 0.333333h;
Ambient temperature;
DOI:10.1248/cpb.37.1717
- Guidance literature:
-
Multi-step reaction with 11 steps
3: 99 percent / DMSO, (COCl)2, Et3N / CH2Cl2
4: 96 percent / PPh3 / benzene / 80 °C
5: 84 percent / n-BuLi / tetrahydrofuran / -78 °C
6: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) oxidation
7: 1.) camphorsulfonic acid, 2.) n-Bu4NF / 1.) room temperature, 2.) dioxane-THF, 65 deg C
8: 88 percent / H2 / Lindlar / methanol
9: 1.) DMSO,(COCl)2, Et3N, 2.) CSA / 1.) CH2Cl2, 2.) CH2Cl2, room temperature
10: (C6H11)2NMgBr / methanol / -55 °C
11: DDQ / CH2Cl2 / 1.5 h / Ambient temperature; buffer (pH 6.86)
With
n-butyllithium; oxalyl dichloride; bis(cyclohexyl)aminomagnesium bromide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
Lindlar's catalyst;
In
tetrahydrofuran; methanol; dichloromethane; benzene;
DOI:10.1016/S0040-4039(00)80703-0