Synthesis of the C1 – C16 fragment of bryostatin for incorporation into 20,20-fluorinated analogues
The stereoselective synthesis of a carboxylic acid ester corresponding to the C1–C16 fragment of bryostatin, with 4-methoxybenzyl (PMB) protection for the 7-hydroxyl group, is reported. The key steps included a Horner-Wadsworth-Emmons reaction between (5R
Mears, Paul R.,Thomas, Eric J.
(2020/12/07)
Activated dimethyl sulfoxide dehydration of amide and its application to one-pot preparation of benzyl-type perfluoroimidates
Various types of primary amides were treated under an activated dimethyl sulfoxide (DMSO) species, (COCl)2-DMSO and Et3N, as a dehydrating agent to obtain nitriles in excellent yield. This dehydration system was extended to a one-pot preparation of perfluoroimidates via volatile perfluoronitriles from perfluoroamides. Fifteen benzyl-type perfluoroimidates can be prepared in 70-90% yield as more stable imidates than the trichloro analogue. MPM- and DMPM-perfluoroimidates can be used to protect alcohols in place of the trichloroacetimidate with excellent chemical properties and in comparable yields.
Nakajima, Noriyuki,Saito, Miho,Ubukata, Makoto
p. 3561 - 3577
(2007/10/03)
Preparation and reaction of 4-methoxybenzyl (MPM) and 3,4- dimethoxybenzyl (DMPM) perfluoroimidates
We have succeeded in one-pot preparation of perfluoroimidates at -78 °C by employing the dehydration of perfluoroamide under the 'activated' dimethyl sulfoxide (DMSO) species followed by in situ nitrile trapping with alcohols. MPM and DMPM perfluoroimidates can be used to protect alcohols in place of the trichloroacetimidate with excellent chemical properties and in comparable yields.
Nakajima, Noriyuki,Saito, Miho,Ubukata, Makoto
p. 5565 - 5568
(2007/10/03)
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