84380-10-9Relevant articles and documents
Facile synthesis of sugar lactols via bromine-mediated oxidation of thioglycosides
Meng, Shuai,Bhetuwal, Bishwa Raj,Acharya, Padam P.,Zhu, Jianglong
, p. 109 - 126 (2019/03/26)
Synthesis of a variety of sugar lactols (hemiacetals) has been accomplished in moderate to excellent yields by using bromine-mediated oxidation of thioglycosides. It was found that acetonitrile is the optimal solvent for this oxidation reaction. This approach involving bromine as oxidant is superior to that using N-bromosuccinimide (NBS) which produces byproduct succinimide often difficult to separate from the lactol products.
Tetranuclear zinc cluster: A dual purpose catalyst for per-: O -acetylation and de- O -acetylation of carbohydrates
Lin, Ting-Wei,Adak, Avijit K.,Lin, Hong-Jyune,Das, Anindya,Hsiao, Wei-Chen,Kuan, Ting-Chun,Lin, Chun-Cheng
, p. 58749 - 58754 (2016/07/07)
The trifluoroacetic acid adduct of tetranuclear zinc cluster Zn4(OCOCF3)6O catalysis in per-O-acetylation and de-O-acetylation of carbohydrates at 70 °C can be tuned by adjusting the reaction medium. Per-O-acetylation of hexopyranoses with a near stoichiometric amount of acetic anhydride in toluene resulted in the exclusive formation of pyranosyl products as an anomeric mixture, whereas de-O-acetylation of acetates occurred in methanol in high yields. In the latter, methanol acts as both nucleophile and solvent, and the reaction conditions were compatible to acid- and base-sensitive groups and amino acid derivatives.
An efficient synthesis of C3 C-alkylated Neu5Ac2en derivatives
Rudrawar, Santosh,Pascolutti, Mauro,Bhatt, Beenu,Thomson, Robin J.,Von Itzstein, Mark
supporting information, p. 1198 - 1201 (2013/03/14)
C3-modified Neu5Ac2en derivatives can be used to study the flexible 150-loop region of influenza virus sialidases and also provide a new template for the development of next-generation sialidase inhibitors. This Letter describes an efficient synthetic route towards the large scale synthesis of C3 C-alkylated Neu5Ac2en derivatives. The key intermediate, a 3-eq-allyl-Neu5Ac derivative, is formed by stereoselective addition of the allyl group in an equatorial configuration at C3, regardless of the stereochemistry of the bromohydrin precursor.
NOVEL GLYCOSYL PHOSPHITES
-
Page/Page column 15, (2012/09/11)
The present invention relates to providing compounds of general formula (1) wherein A is glycosyl residue of a mono-, di- or oligosaccharide in protected form and R is selected from optionally substituted aryl or optionally substituted heteroaryl, methods
Chemical Synthesis and Enzymatic Testing of CMP-Sialic Acid Derivatives
Wolf, Saskia,Warnecke, Svenja,Ehrit, Joerg,Freiberger, Friedrich,Gerardy-Schahn, Rita,Meier, Chris
, p. 2605 - 2615 (2013/01/16)
The cycloSal approach has been used in the past for the synthesis of a range of phosphorylated bioconjugates. In those reports, cycloSal nucleotides were allowed to react with different phosphate nucleophiles. With glycopyranosyl phosphates as nucleophile
PRODUCTION OF 6'-O-SIALYLLACTOSE AND INTERMEDIATES
-
Page/Page column 46, (2011/09/19)
The present invention relates to a method for preparation of the trisaccharide 6'-0-sialyllactose (formula (I)) or salts thereof as well as intermediates in the synthesis and for the use of 6'-0-sialyllactose salts in pharmaceutical or nutritional composi
Toward fully synthetic homogeneous β -human Follicle-Stimulating hormone (β -hFSH) with a biantennary N-linked dodecasaccharide. synthesis of β -hFSH with chitobiose units at the natural linkage sites
Nagorny, Pavel,Fasching, Bernhard,Li, Xuechen,Chen, Gong,Aussedat, Baptiste,Danishefsky, Samuel J.
supporting information; experimental part, p. 5792 - 5799 (2009/09/24)
A highly convergent synthesis of the sialic acid-rich biantennary N-linked glycan found in human glycoprotein hormones and its use in the synthesis of a fragment derived from the β -domain of human Follicle-Stimulating Hormone (hFSH) are described. The synthesis highlights the use of the Sinay radical glycosidation protocol for the simultaneous installation of both biantennary side-chains of the dodecasaccharide as well as the use of glycal chemistry to construct the tetrasaccharide core in an efficient manner. The synthetic glycan was used to prepare the glycosylated 20-27aa domain of the β -subunit of hFSH under a Lansbury aspartylation protocol. The proposed strategy for incorporating the prepared N-linked dodecasaccharide-containing 20-27aa domain into β -hFSH subunit was validated in the context of a model system, providing protected β -hFSH subunit functionalized with chitobiose at positions 7 and24.
Versatile acetylation of carbohydrate substrates with bench-top sulfonic acids and application to one-pot syntheses of peracetylated thioglycosides
Chao, Chin-Sheng,Chen, Min-Chun,Lin, Shih-Che,Mong, Kwok-Kong T.
, p. 957 - 964 (2008/09/17)
Inexpensive and readily available sulfonic acids, p-toluenesulfonic acid, and sulfuric acid are versatile and efficient catalysts for the peracetylation of a broad spectrum of carbohydrate substrates in good yield and in a practical time frame. Three appealing features in sulfonic acid-catalyzed acetylation of free sugars were explored including (1) suppression of furanosyl acetate formation for d-galactose and l-fucose; (2) high yielding chemoselective acetylation of sialic acid under appropriate conditions; and (3) peracetylation of amino sugars with different amino protecting functions. Simple one-pot two step acetylation-thioglycosidation methods for the expeditious synthesis of p-tolyl per-O-acetyl thioglycosides were also delineated.
Highly efficient α-sialylation by virtue of fixed dipole effects of N-phthalyl group: Application to continuous flow synthesis of α(2-3)-and α(2-6)-Neu5Ac-Gal motifs by microreactor
Tanaka, Shin-Ichi,Goi, Takashi,Tanaka, Katsunori,Fukase, Koichi
, p. 369 - 394 (2008/04/12)
Highly α-selective sialylation of sialic acid N- phenyltrifluoroacetimidate with various galactose and lactose acceptors has been achieved by introducing the C-5 N-phthalyl group on the donor. The "fixed dipole effect" of the N-phthalyl group was proposed to explain the high reactivity and α-selectivity. The microfluidic system was applied to the present α-sialylation, which is amenable to large-scale synthesis. The N-phthalyl group was removed by treatment with methylhydrazine acetate, for which protocol can be readily applied to the synthesis of a variety of sialic acid-containing oligosaccharides. (Chemical Equation Presented). Copyright Taylor & Francis Group, LLC.
Large-scale synthesis of per-O-acetylated saccharides and their sequential transformation to glycosyl bromides and thioglycosides
Lin, Chan-Ching,Huang, Li-Cheng,Liang, Pi-Hui,Liu, Ching-Yang,Lin, Chun-Cheng
, p. 303 - 313 (2007/10/03)
This work describes a large-scale synthesis of per- O -acetylated mono- and disaccharides using a stoichiometric amount of acetic anhydride in the presence of LiClO 4 under solvent-free conditions. The peracetylated saccharides underwent subsequent anomeric bromination and thioglycosidation in one-pot to yield synthetically valuable building blocks. Copyright Taylor & Francis Group, LLC.
