136994-78-0Relevant articles and documents
Stereodivergent Syntheses of All Stereoisomers of (?)-Shikimic Acid: Development of a Chiral Pool for the Diverse Polyhydroxy-cyclohexenoid (or -cyclohexanoid) Bioactive Molecules
He, Yun-Gang,Huang, Yong-Kang,Xu, Zhang-Li,Xie, Wen-Jing,Luo, Yong-Qiang,Li, Feng-Lei,Zhu, Xing-Liang,Shi, Xiao-Xin
, p. 4318 - 4332 (2021/07/21)
Novel stereodivergent total syntheses of all the seven stereoisomers of (?)-shikimic acid [(?)-SA 1] have been systematically performed. (+)-ent-SA ent-1 was synthesized from (?)-SA 1 via 9 steps in 31 % overall yield; (?)-3-epi-SA 2 was synthesized from (?)-SA 1 via 5 steps in 66 % overall yield; (+)-3-epi-ent-SA ent-2 was synthesized from (?)-SA 1 via 7 steps in 43 % overall yield; (?)-4-epi-SA 3 was synthesized from (?)-SA 1 via 11 steps in 32 % overall yield; (+)-4-epi-ent-SA ent-3 was synthesized from (?)-SA 1 via 7 steps in 42 % overall yield; (?)-5-epi-SA 4 was synthesized from (?)-SA 1 via 6 steps in 56 % overall yield; and (+)-5-epi-ent-SA ent-4 was synthesized from (?)-SA 1 via 12 steps in 29 % overall yield. The stereochemistry of all the above seven stereoisomers of (?)-SA 1 were further studied by two dimensional (2D) 1H NMR technique.
Process for synthesizing oseltamivir sulfonate from quinic acid
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, (2021/01/04)
The invention discloses a process for synthesizing oseltamivir sulfonate from quinic acid. The process specifically comprises the following steps of: S1, adding quinic acid and ethyl acetate into a round-bottom flask, and adding p-toluenesulfonic acid and 2, 2-dimethoxypropane, carrying out reaction to obtain a brown solid 2; S2, adding the brown solid 2 and dichloromethane into the round-bottom flask, dropwise adding methanesulfonyl chloride and triethylamine into the round-bottom flask while performing stirring, and carrying out reaction to obtain an intermediate 3; S3, adding the obtained intermediate 3 into a three-neck flask, adding ethanol and sodium ethoxide for reaction, and removing the dichloromethane after finishing the reaction to obtain an intermediate 4; and S4, adding the intermediate 4 and dichloromethane into the round-bottom flask, dropwise adding the methanesulfonyl chloride and triethylamine into the round-bottom flask while performing stirring, extracting a reaction solution with dichloromethane and water after finishing the reaction, concentrating an obtained organic phase under reduced pressure, adding methanol for crystallization, and performing filtering toobtain a white crystal 5, namely oseltamivir sulfonate.
Chemo-enzymatic enantioconvergent approach toward ethyl shikimate from ethyl 5-hydroxy-3,4-isopropylidenedioxycyclohex-1-enecarboxylate
Yamashita, Yasunobu,Hanaya, Kengo,Sugai, Takeshi,Mizushima, Tohru,Shoji, Mitsuru
, p. 6527 - 6532 (2013/07/26)
An enantioconvergent route for natural form of ethyl shikimate was achieved from Diels-Alder adduct of furan and acryloyl chloride. The key step was a highly enantioselective (E >500) and efficient acetylation of ethyl (3R*,4S*,5S*)-5-hydroxy-3,4-isopropylidenedioxycyclohex-1- enecarboxylate, which had a diastereomeric relationship with ethyl shikimate, mediated by Burkholderia cepacia lipase (Amano PS-IM). Both of the resolved enantiomers were converted to natural form of ethyl shikimate by inversion at C-5 for the former and at C-3 and C-4 for the latter, respectively.