35303-86-7Relevant academic research and scientific papers
Streamlined access to carbohydrate building blocks: Methyl 2,4,6-tri-O-benzyl-α-D-glucopyranoside
Demchenko, Alexei V.,Kashiwagi, Gustavo A.,Shrestha, Ganesh,Stine, Keith J.
, (2021/12/02)
Presented herein is an improved synthesis of a common 3-OH glycosyl acceptor. This compound is a building block that is routinely synthesized by many research groups to be used in glycosylation refinement studies. The only known direct synthesis by Koto lacks regioselectivity and relies on chromatography separation using hazardous solvents. Our improved synthetic approach relies on Koto's selective benzylation protocol, but it is followed by acylation-purification-deacylation sequence. Although this approach involves additional manipulations, it provides consistent results and is superior to other indirect strategies. Also obtained, albeit in minor quantities, is 4-OH acceptor, another common building block.
A Chiral Copper Catalyzed Site-Selective O-Alkylation of Carbohydrates
Ren, Bo,Wang, Jiaxi,Zhang, Mengyao,Chen, Yue,Zhao, Wei
supporting information, p. 665 - 670 (2021/12/02)
Highly regioselective alkylation of sugar hydroxyl groups has always been an important challenge in carbohydrate chemistry, especially for the selective alkylation of trans diols, there is no direct and efficient catalytic method so far. A chiral copper c
Introducing Oxo-Phenylacetyl (OPAc) as a Protecting Group for Carbohydrates
Kumar, Atul,Gannedi, Veeranjaneyulu,Rather, Suhail A.,Vishwakarma, Ram A.,Ahmed, Qazi Naveed
, p. 4131 - 4138 (2019/04/30)
A series of oxo-phenylacetyl (OPAc)-protected saccharides, with divergent base sensitivity profiles against benzoyl (Bz) and acetyl (Ac) were synthesized, and KHSO5/AcCl in methanol was identified as an easy, mild, selective, and efficient deprotecting reagent for their removal in the perspective of carbohydrate synthesis. Timely monitoring of AcCl reagent was supportive in both sequential and simultaneous deprotecting of OPAc, Bz, and Ac. The salient feature of our method is the orthogonal stability against different groups, its ease to generate different valuable acceptors using designed monosaccharides, and use of OPAc as a glycosyl donar.
An easy and versatile approach for the regioselective De-O-benzylation of protected sugars based on the I2/Et3SiH combined system
Pastore, Antonello,Valerio, Silvia,Adinolfi, Matteo,Iadonisi, Alfonso
experimental part, p. 5881 - 5889 (2011/06/24)
The use of cheap and easy to handle reagents, such as I2 and Et3SiH, at low temperature allows the regioselective removal of benzyl protecting groups from highly O-benzylated carbohydrates. The observed regioselectivity is dependent
μ-Waves avoid large excesses of diisobutylaluminium-hydride (DIBAL-H) in the debenzylation of perbenzylated α-cyclodextrin
Zaborova, Elena,Blériot, Yves,Sollogoub, Matthieu
scheme or table, p. 1254 - 1256 (2010/04/29)
Regioselective double deprotection of cyclodextrins using diisobutylaluminium-hydride (DIBAL-H) has become an important tool in functional cyclodextrin synthesis. When conventionally heated a very large excess of reagent is necessary for the reaction to happen, when μ-waves irradiation is employed the quantity of DIBAL-H can be lowered down to 5 equiv. Reaction with a smaller quantity of DIBAL-H never achieved complete double debenzylation. These results also sustain the mechanistic hypothesis according to which a minimum of two aluminium atoms are necessary for each debenzylation to occur.
Synthesis of ether-linked sugar by nucleophilic opening of carbohydrate oxiranes
Nishiyama, Kazusa,Nakayama, Takahiro,Natsugari, Hideaki,Takahashi, Hideyo
experimental part, p. 3761 - 3768 (2009/06/06)
A new synthesis of ether-linked sugar utilizing the nucleophilic ring-opening reaction of carbohydrate α- or β-oxirane was developed. The reaction of 2,3-anhydro-α-D-mannopyranosides resulted in the expected high regioselectivity. In contrast, 2,3-anhydro-α-D-allopyranosides showed an unusual regioselectivity shift. The differentiating properties of carbohydrate α- or β-oxirane were investigated by comparing various conditions of the reaction. Georg Thieme Verlag Stuttgart.
Regioselective de-O-benzylation of monosaccharides
Falck,Barma,Venkataraman, Sylesh K.,Baati, Rachid,Mioskowski, Charles
, p. 963 - 966 (2007/10/03)
Poly-O-benzylated sugars are regioselectively debenzylated using CrCl2/LiI in moist EtOAc. A predictive, three-point coordination model is proposed.
p-Methoxybenzyl ether cleavage by polymer-supported sulfonamides.
Hinklin, Ronald J,Kiessling, Laura L
, p. 1131 - 1133 (2007/10/03)
[reaction: see text] p-Methoxybenzyl ethers have been found to transfer from alcohols to sulfonamides in the presence of catalytic trifluoromethanesulfonic acid. This process for protecting group removal can be performed in solution with yields >94%. Through the use of sulfonamide-functionalized ("safety-catch") resins, p-methoxybenzyl ethers can be cleaved in excellent yields with minimal purification.
Design and synthesis of a trisubstrate analogue for α(1 →3)fucosyltransferase: A potential inhibitor
Heskamp,Veeneman,Van Der Marel,Van Boeckel,Van Boom
, p. 8397 - 8406 (2007/10/02)
Phenyl 1-azido-3,4,5-tri-O-benzyl-I-deoxy-2-seleno-α-1-fuco-heptulopyranoside (5), readily accessible from perbenzylated 1-fucono-1,5-lactone, is a key intermediate in the preparation of trisubstrate analogue 2. NIS mediated condensation of fucosyl donor 5 with methyl 2,4,6-tri-O-benzyl-α-d-glucopyranoside (7) and ensuing reduction of the azido function furnished ketodisaccharide 10b, which was elongated at the 1-amino group of the fucose residue with a malonic acid spacer. The thus obtained compound was deprotected and subsequently coupled with 5′-amino-5′-deoxy-guanosine to afford the target compound 2.
A STEREOSELECTIVE α-GLUCOSYLATION BY USE OF A MIXTURE OF 4-NITROBENZENESULFONYL CHLORIDE, SILVER TRIFLUOROMETHANESULFONATE, N,N-DIMETHYLACETAMIDE, AND TRIETHYLAMINE
Koto, Shinkiti,Morishima, Naohiko,Owa, Miho,Zen, Shonosuke
, p. 73 - 84 (2007/10/02)
Stereoselective α-glucosylation of partially protected carbohydrates with 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose in dichloromethane, in the presence of a quaternary mixture of 4-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, N,N-dimethylacetamide, and triethylamine gave O-α-D-glucopyranosyl-(1->4)- and -(1->6)-2-acetamido-2-deoxy-D-glucopyranose (N-acetylmaltosamine and N-acetylisomaltosamine).A step-by-step synthesis of O-α-D-glucopyranosyl-(1->4)-O-6)>-D-glucopyranose is described.
