ChemInform Abstract: Benzyl N‐Phenyl‐2,2,2‐trifluoroacetimidate: A New and Stable Reagent for O‐Benzylation.

Okada, Yasunori; Ohtsu, M.; Bando, Masafumi; Yamada, Hidetoshi

doi:10.1002/chin.200801045

Cited by 2 publications

(2 citation statements)

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“…Benzyl N-phenyl-2,2,2-trifluoroacetimidate, which served as a new O-benzylation reagent, was reported by Yamada and coworkers (Scheme 29). 48 The O-benzylation reagent was readily prepared by the NaH-promoted coupling reaction of benzyl alcohol with trifluoroacetimidoyl chlorides. The present tri-fluoroacetimidate was very stable and soluble in various solvents, which could react with sterically hindered alcohols and base-sensitive hydroxyl esters apart from common alcohols to deliver benzyl ethers in the presence of catalytic TMSOTf.…”

Section: C-o(s) Bond Formationmentioning

confidence: 99%

Trifluoroacetimidoyl halides: a potent synthetic origin

Chen

2020

Org. Chem. Front.

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Section: C-o(s) Bond Formationmentioning

confidence: 99%

Trifluoroacetimidoyl halides: a potent synthetic origin

Chen

2020

Org. Chem. Front.

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“…Most pleasingly, the yield of 28 was significantly improved up to 67% when this reaction proceeded in 1,4‐dioxane with benzyl 2,2,2‐trifluoro‐ N ‐phenylacetimidate (BnOPTFAI) and a catalytic amount of TfOH. [ 57 ] Finally, removal of allyl group at rhamnosyl…”

Section: Background and Originality Contentmentioning

confidence: 99%

Chemical Synthesis of an Octasaccharide Derivative Related to Group B StreptococcusCell‐Wall Polysaccharide

et al. 2022

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Comprehensive Summary Group B Streptococcus (GBS) is the major pathogen that causes invasive infectious diseases in neonates and infants. The development of preventive and therapeutic strategies against GBS infection has been becoming the most pressing subject worldwide. Group B carbohydrate (GBC), the group B‐specific polysaccharide that distinguishes GBS with other streptococci species, has been identified as an attractive antigen for diagnosis and vaccine development because of its highly conservative tetra‐antennary structure. In this paper, a highly convergent [3 + 5] glycosylation strategy for efficient synthesis of an octasaccharide derivative related to GBC oligosaccharide unit II has been developed. In this synthesis, each glycosylation reaction was efficiently constructed with glycosyl imidates, especially trifluoroacetimidate, as donors, and each glycosidic bond was stereoselectively controlled via the neighboring group participation effect of acyl group on the 2‐O‐position of imidate donors or the solvent effect of Et2O. Furthermore, the aminoethylphosphate group was smoothly installed on the 6‐O‐position of d‐glucitol residue using the phosphoramidite method. After global deprotection, the target octasaccharide was successfully obtained from d‐glucitol in 29 steps with an overall yield of 1.37%. The free amino group installed on the aminoethylphosphate spacer of the target molecule enables its modification with functionalized biomolecules for further biological studies.

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ChemInform Abstract: Benzyl N‐Phenyl‐2,2,2‐trifluoroacetimidate: A New and Stable Reagent for O‐Benzylation.

Cited by 2 publications

References 1 publication

Trifluoroacetimidoyl halides: a potent synthetic origin

Trifluoroacetimidoyl halides: a potent synthetic origin

Chemical Synthesis of an Octasaccharide Derivative Related to Group B StreptococcusCell‐Wall Polysaccharide

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