116183-75-6Relevant academic research and scientific papers
Carbon glycoside glycosylated tetravalent platinum compound as well as synthesis method and application thereof
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Paragraph 0064; 0075-0077, (2021/07/08)
The invention provides a carbon glycoside glycosylated tetravalent platinum compound, a synthesis method and application thereof. R1 and R2 are independently C1-C4 lower alkanes, R3 is glucose, galactose, mannose and ribose, different sugars are used as raw materials, and a series of carbon glycoside glycosylated tetravalent platinum compounds are synthesized through protection and deprotection reaction and metallization reaction of the sugars. The synthesis method is simple, the used raw materials are cheap and easy to obtain, the glycosylated tetravalent platinum compound has the capacity of targeting glucose transporter protein and has potential application value in the field of cancer treatment, introduction of a C-glucosidic bond enables the series of compounds to have the capacity of resisting hydrolysis of beta-glucosidase, and the compound is expected to be applied to the field of oral antitumor drugs.
Building a macrocyclic toolbox from C-linked carbohydrates identifies antiangiogenesis agents from zebrafish assay
Jogula, Srinivas,Dasari, Bhanudas,Khatravath, Mahender,Chandrasekar, Gayathri,Kitambi, Satish Srinivas,Arya, Prabhat
supporting information, p. 5036 - 5040 (2013/11/06)
We report the synthesis of four different types of macrocyclic-derived glycohybrids from carbohydrates that have an amino acid moiety in the large-ring skeleton. These macrocyclic glycohybrids were obtained from α-C-1H- and β-C-1H-linked carbohydrates. In one series, we utilized ring-closing metathesis as the "stitching technology" to obtain two different macrocycles, i.e., trans equatorial-axial C-1H and C-5H and cis axial-axial C-1H and C-5H. The click approach was the key reaction in our second series to obtain two other macrocyclic compounds, i.e., trans equatorial-axial C-1H and C-5H and cis axial-axial C-1H and C-5H. The evaluation of this toolbox resulted in the identification of two unique compounds as antiangiogenesis agents in an embryonic zebrafish assay. Interestingly, in both cases, the macrocyclic compounds that have a cis relationship (i.e., axial-axial orientation) between C-1H and C-5H showed activity and their other diastereomers (i.e., equatorial-axial C-1H and C-5 H) with a trans relationship did not show any effect. The synthesis of four different types of macrocyclic glycohybrids that contain an amino acid moiety in the large-ring skeleton is reported. Ring-closing metathesis and click chemistry approaches were utilized to obtain two different series of macrocycles. The evaluation of this toolbox resulted in the identification of two unique compounds as antiangiogenesis agents in an embryonic zebrafish assay. Copyright
Alkylidenation of sugar lactones and further transformation to C-glycosides
Xie, Juan,Molina, Adeline,Czernecki, Stanislas
, p. 481 - 498 (2007/10/03)
The Wittig reaction of (carbethoxymethylene)triphenylphosphorane with perbenzylated sugar δ-lactones and their 2-acetamido-2-deoxy derivatives is described. It is shown that this olefination occurred readily with the galacto and gluco derivatives, leading stereoselectively to Z-C-glycosylidenes in good yields. However, the same reaction with the perbenzylated 2-deoxy-D-arabino-hexono-1,5-lactone and the mannonolactones worked poorly. Reduction over Pd/C followed by acetylation of the obtained C-glycosylidenes led stereoselectively to peracetylated β-C-glycosides and amino β-C-glycosides. The olefin function could also be reduced selectively by Raney nickel or NiCl2/NaBH4, affording the perbenzylated C-glycosides and amino β-C-glycosides. Other transformation of the enol ether function is also reported.
The Wittig-Horner Reaction on 2,3,4,6-Tetra-O-benzyl-D-mannopyranose and 2,3,4,6-Tetra-O-benzyl-D-glucopyranose
Allevi, Pietro,Ciuffreda, Pierangela,Colombo, Diego,Monti, Diego,Speranza, Giovanna,Manitto, Paolo
, p. 1281 - 1283 (2007/10/02)
The synthetic utility of the Wittig-Horner reaction in the synthesis of C-glycosides is illustrated by the preparation of the α- and β-glycosyl acetates of the 2,3,4,6-tetra-O-benzyl-D-mannopyranose and of the 2,3,4,6-tetra-O-benzylglucopyranose.A partial epimerization of the C-2 carbon of the starting protected carbohydrate is observed.
A CONVENIENT SYNTHESIS OF BOTH THE ANOMERS OF ETHYL (2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSYL)ACETATE
Monti, Diego,Gramatica, Paola,Speranza, Giovanna,Manitto, Paolo
, p. 5047 - 5048 (2007/10/02)
The α- and β-anomers of ethyl (2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)acetate, useful intermediates for the synthesis of alkyl C-glucosides, can be obtained in good yields by reaction of tetra-O-benzylglucose with triethyl phosphonoacetate according to t
