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1-碘甘油醛：一种用于通过羰基化交叉偶联反应合成d-糖酰胺和酯的多功能中间体。

1-Iodoglycal: A Versatile Intermediate for the Synthesis of d-Glyco Amides and Esters Employing Carbonylative Cross-Coupling Reaction.

作者信息

Hornink Milene M, Toledo Monica F Z J, Pimenta Daniel C, Paschoalin Caio, Silva Pamela M, Figlino Giuseppe E, Aguiar Eurípedes, Cervi Gustavo, Ribeiro Francisco W M, Carita Correra Thiago, Ferry Angélique, Stefani Hélio A

机构信息

Departamento de Farmácia, Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, São Paulo 05508-900, SP, Brasil.

Instituto Butantan, São Paulo 05503-900, SP, Brasil.

出版信息

ACS Omega. 2024 Jul 11;9(29):31732-31744. doi: 10.1021/acsomega.4c02645. eCollection 2024 Jul 23.

DOI:10.1021/acsomega.4c02645
PMID:39072121
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11270555/
Abstract

In this study, we present the development of two catalytic processes: a Pd-PEPPSI-catalyzed aminocarbonylation and a Pd(OAc)-Xantphos-catalyzed alkoxycarbonylation of d-glycals, utilizing carbonylative cross-coupling reactions. We explored successfully various types of aromatic amines, as well as alkyl amines and amino acids, to synthesize new d-glycal amides. However, we observed limitations in the reactivity of alkyl and heteroaromatic amines. The processes enabled the synthesis of 20 novel C1-branched glycoamides and 7 new d-gluco esters.

摘要

在本研究中，我们展示了两种催化过程的进展：一种是钯-吡啶双齿膦配体催化剂催化的氨羰基化反应，另一种是醋酸钯-联二萘二苯基膦催化剂催化的d-甘醇的烷氧基羰基化反应，均利用羰基化交叉偶联反应。我们成功探索了各种类型的芳香胺、脂肪胺和氨基酸，以合成新的d-甘醇酰胺。然而，我们观察到脂肪胺和杂芳胺的反应活性存在局限性。这些过程实现了20种新型C1-支链糖酰胺和7种新的d-葡萄糖酯的合成。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5c13/11270555/c99a85d7863c/ao4c02645_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5c13/11270555/bf8301dcc299/ao4c02645_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5c13/11270555/54925012ed35/ao4c02645_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5c13/11270555/8dccf5806d28/ao4c02645_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5c13/11270555/61107d5cf03e/ao4c02645_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5c13/11270555/c99a85d7863c/ao4c02645_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5c13/11270555/bf8301dcc299/ao4c02645_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5c13/11270555/54925012ed35/ao4c02645_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5c13/11270555/8dccf5806d28/ao4c02645_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5c13/11270555/61107d5cf03e/ao4c02645_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5c13/11270555/c99a85d7863c/ao4c02645_0005.jpg

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