Stereoselective Organocatalyzed Glycosylation of Glycosyl Trichloroacetimidate Donors: Thiouracil as Bronsted Acid Catalyst

被引：1
|
作者：
Tiwari, Ashwani [1 ,2 ]
Khanam, Ariza [1 ]
Lal, Mohan [1 ,2 ]
Mandal, Pintu Kumar [1 ,2 ]
机构：
[1] CSIR Cent Drug Res Inst, Med & Proc Chem Div, BS-10-1,Sect 10,Jankipuram Extens,Sitapur Rd,POB 1, Lucknow 226031, India
[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2024年 / 366卷 / 15期
关键词：
Organocatalyst; 2-Thiouracil; Glycosylation; O-Glycosides; alpha-Stereoselective; ACTIVATION; THIOUREAS; ACT;
D O I：
10.1002/adsc.202400067
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
Herein, we report thiouracil-catalyzed alpha-selective O-glycosylations employing easily accessible glycosyl trichloroacetimidate donors without using any co-catalyst or additive. A variety of alcohol nucleophiles including saccharides, and amino acids with different protecting groups containing glycosyl trichloroacetimidate donors were successfully alpha-glycosylated using an operationally simple protocol. Moreover, mechanistic investigations suggest that thiouracil functions as Br & oslash;nsted acid/base catalyst in this glycosylation process.
引用
收藏
页码：3262 / 3268
页数：7
相关论文
共 41 条
  • [21] Stereoselective cis glycosylation of 2-O-allyl protected glycosyl donors by intramolecular aglycon delivery (IAD)
    Seward, CMP
    Cumpstey, I
    Aloui, M
    Ennis, SC
    Redgrave, AJ
    Fairbanks, AJ
    CHEMICAL COMMUNICATIONS, 2000, (15) : 1409 - 1410
  • [22] Dehydrative glycosylation in water using a bronsted acid-surfactant-combined catalyst
    Aoyama, N
    Kobayashi, S
    CHEMISTRY LETTERS, 2006, 35 (02) : 238 - 239
  • [23] Stereoselective Aromatic O-Glycosylation of Glycosyl Chloride with Arylboronic Acid under an Air Atmosphere
    Lai, Jinsheng
    Wu, Shuqin
    Zhou, Zhuoyi
    Liu, Hui
    Tu, Yuanhong
    Zhang, Qingju
    Wang, Liming
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (15): : 10721 - 10734
  • [24] S-Benzoxazolyl (SBox) glycosides as novel, versatile glycosyl donors for stereoselective 1,2-cis glycosylation
    Demchenko, AV
    Malysheva, NN
    De Meo, C
    ORGANIC LETTERS, 2003, 5 (04) : 455 - 458
  • [25] Stereoselective glycosylation with conformation-constrained 2-Nitroglycals as donors and bifunctional thiourea as catalyst
    Wan, Yongyong
    Wu, Xiaopei
    Xue, Yunxia
    Lin, Xi-E
    Wang, Liming
    Sun, Jian-Song
    Zhang, Qingju
    JOURNAL OF CARBOHYDRATE CHEMISTRY, 2021, 40 (7-9) : 535 - 557
  • [26] Novel glycosylation reactions using glycosyl thioimidates of N-acetylneuraminic acid as sialyl donors
    Ikeda, K
    Aizawa, M
    Sato, K
    Sato, M
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (10) : 2618 - 2620
  • [27] Organocatalytic stereoselective cationic polymerization of vinyl ethers by employing a confined bronsted acid as the catalyst
    Yang, Zan
    Zhang, Xun
    Jiang, Yu
    Ma, Qiang
    Liao, Saihu
    SCIENCE CHINA-CHEMISTRY, 2022, 65 (02) : 304 - 308
  • [28] Iodine-triphenylphosphine triggers an easy one-pot alpha stereoselective dehydrative glycosylation on hemiacetalic benzylated glycosyl donors
    Imperio, Daniela
    Brentazzoli, Marco
    Valloni, Filippo
    Minassi, Alberto
    Panza, Luigi
    CARBOHYDRATE RESEARCH, 2023, 533
  • [29] Regioselective and 1,2-cis--Stereoselective Glycosylation Utilizing Glycosyl-Acceptor-Derived Boronic Ester Catalyst
    Nakagawa, Akira
    Tanaka, Masamichi
    Hanamura, Shun
    Takahashi, Daisuke
    Toshima, Kazunobu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (37) : 10935 - 10939
  • [30] Stereoselective O-glycosylation reactions using glycosyl donors with diphenylphosphinate and propane-1,3-diyl phosphate leaving groups
    Vankayalapati, H
    Singh, G
    Tranoy, I
    TETRAHEDRON-ASYMMETRY, 2001, 12 (09) : 1373 - 1381
12345