1301176-84-0Relevant academic research and scientific papers
Gold(III)-Catalyzed Glycosylation using Phenylpropiolate Glycosides: Phenylpropiolic Acid, An Easily Separable and Reusable Leaving Group
Shaw, Mukta,Thakur, Rima,Kumar, Amit
, p. 589 - 605 (2019/01/14)
An efficient and operationally simple gold(III)-catalyzed glycosylation protocol was developed using newly synthesized benchtop stable phenylpropiolate glycosyl (PPG) donors. Gold(III)-catalyzed activation of PPGs proceeds well with various carbohydrate a
A flexible 1,2-cis α-glycosylation strategy based on in situ adduct transformation
Hu, Jhe-Cyuan,Feng, Ai-Fen Wendy,Chang, Bo-Yao,Lin, Chun-Hung,Mong, Kwok-Kong Tony
, p. 5345 - 5356 (2017/07/10)
A flexible 1,2-cis α-selective glycosylation strategy for a wide range of glycosyl donors and acceptors has been developed, which is based on an in situ adduct transformation protocol. Based on this strategy, both NFM-derived and iodide covalent adducts c
Co2(CO)6-propargyl cation mediates glycosylation reaction by using thioglycoside
Xia, Meng-jie,Yao, Wang,Meng, Xiang-bao,Lou, Qing-hua,Li, Zhong-jun
supporting information, p. 2389 - 2392 (2017/05/29)
We discovered that the cobalt-propargyl cation can mediate the glycosylation reaction by activating the thioglycoside donor. The glyco-oxacarbenium cation was formed by transferring the thio-aglycone to the cobalt-propargyl cation that was generated from the cobalt-propargylated acceptor in situ via the activating with Lewis acid. The reactivity of the donor (Armed or dis-armed) and the amount of the Lewis acid control the releasing rate of the cobalt-propargyl group.
Halobenzoyl groups in glycosylation: Effect on stereoselectivity and reactivity of glycosyl donors
Visansirikul,Yasomanee,Demchenko
, p. 1107 - 1118 (2016/02/09)
Described herein is the synthesis and evaluation of a series of glycosyl donors equipped with halobenzoyl substituents at O(4) and O(6) to study their properties in glycosylations. Among possible effects that may include carbonyl participation or H-bond m
Glycosidation of thioglycosides in the presence of bromine: Mechanism, reactivity, and stereoselectivity
Kaeothip, Sophon,Yasomanee, Jagodige P.,Demchenko, Alexei V.
, p. 291 - 299 (2012/03/08)
Elaborating on previous studies by Lemieux for highly reactive "armed" bromides, we discovered that β-bromide of the superdisarmed (2-O-benzyl-3,4,6-tri-O-benzoyl) series can be directly obtained from the thioglycoside precursor. When this bromide is glycosidated, α-glycosides form exclusively; however, the yields of such transformations may be low due to the competing anomerization into α-bromide that is totally unreactive under the established reaction conditions.
Armed-disarmed effect of remote protecting groups on the glycosylation reaction of 2,3-dideoxyglycosyl donors
Tomono, Satoshi,Kusumi, Shunichi,Takahashi, Daisuke,Toshima, Kazunobu
supporting information; experimental part, p. 2399 - 2403 (2011/05/16)
The armed-disarmed effect of remote protecting groups at the C-4 and/or C-6 position(s) on the glycosylation reactions of 2,3-dideoxyglycosyl donors was investigated. It was found that under various glycosylation conditions, 4- or 6-O-Bn 2,3-dideoxyglycos
