196703-95-4Relevant academic research and scientific papers
A Synthetic Bioinspired Carbohydrate Polymer with Mucoadhesive Properties
Balijepalli, Anant S.,Sabatelle, Robert C.,Chen, Mingfu,Suki, Bela,Grinstaff, Mark W.
, p. 704 - 710 (2020)
Mucoadhesive polymers are of significant interest to the pharmaceutical, medical device, and cosmetic industries. Polysaccharides possessing charged functional groups, such as chitosan, are known for mucoadhesive properties but suffer from poor chemical d
A substrate-based approach to skeletal diversity from dicobalt hexacarbonyl (C1)-alkynyl glycals by exploiting its combined ferrier-nicholas reactivity
Lobo, Fernando,Gomez, Ana M.,Miranda, Silvia,Lopez, J. Cristobal
, p. 10492 - 10502 (2014/08/18)
Novel substrates that combine dicobalt hexacarbonyl propargyl (Nicholas) and pyranose-derived allylic (Ferrier) cations have been generated by treatment of hexacarbonyldicobalt (C-1)-alkynyl glycals with BF3 .Et2O. The study of these cations has resulted in the discovery of novel reaction pathways that have shown to be associated to the nature of O-6 substituent in the starting alkynyl glycals. Accordingly, compounds resulting from ring expansion (oxepanes), ring contraction (tetrahydrofurans), or branched pyranoses, by incorporation of nucleophiles, can be obtained from 6-O-benzyl, 6-hydroxy, or 6-O-silyl derivatives, respectively. The use of a 6-O-allyl alkynyl glycal led to a suitable funtionalized oxepane able to experience an intramolecular Pauson-Khand cyclization leading to a single tricyclic derivative.
Improved and large-scale synthesis of different protected d-glucuronals
Mikula, Hannes,Matscheko, Dominik,Schwarz, Markus,Hametner, Christian,Fr?hlich, Johannes
, p. 19 - 23 (2013/04/23)
Although different protected d-glucuronals are used as precursors for the preparation of many compounds, standard procedures and large-scale syntheses are still not described in the literature. In the course of the development of different protected d-glucuronyl donors we developed several versatile methods that can be used for fast and reproducible preparation of large amounts of the key intermediates. d-Glucuronolactone was converted to methyl 3,4-di-O-acetyl-d-glucuronal applying a novel one-pot protocol, which allowed for large-scale synthesis. Introduction of silyl and benzyl groups was achieved using optimized procedures. Furthermore 3,4,6-tri-O-acetyl-d-glucal was used as starting material for an improved preparation of benzyl protected d-glucuronal, which significantly accelerates and simplifies similar methods described in the literature.
2-(Dimethyl (2-naphthylmethyl)silyl) ethoxy carbonate (NSEC) as a new mode of hydroxyl group protection
Bufali, Simone,Hoelemann, Alexandra,Seeberger, Peter H.
, p. 441 - 462 (2007/10/03)
2-[Dimethyl(2-naphthylmethyl)silyl]ethoxy carbonate (NSEC) is a novel protecting group to mask hydroxyl groups. NSECCl is available in three steps from chlorodimethylvinylsilane and 2-(bromomethyl)naphthalene. Introduction and removal of the NSEC group ar
Automated Synthesis of Oligosaccharides
Palmacci, Emma R.,Plante, Obadiah J.,Hewitt, Michael C.,Seeberger, Peter H.
, p. 3975 - 3990 (2007/10/03)
The chemical synthesis of oligosaccharides with an automated solid-phase synthesizer is described. An octenediol linker served to attach the growing oligosaccharide chain to the solid support, and the desired structures were cleaved from the support via o
Linker influence on the stereochemical outcome of glycosylations utilizing solid support-bound glycosyl phosphates
Hunt, Diana K.,Seeberger, Peter H.
, p. 2751 - 2754 (2007/10/03)
(Matrix presented) Glycosyl phosphates can be readily accessed on a solid support via a three-step procedure from support-bound glycals. These resin-bound glycosyl phosphates were successfully used as glycosylating agents for coupling with a series of nuc
The particular sensitivity of silyl ethers of D-glucal toward two Vilsmeier - Haack reagents POCl3·DMF and (CF3SO2)2O·DMF. Their unique and selective conversion to the corresponding C(6)-O-formates
Lellouche,Koeller
, p. 693 - 696 (2007/10/03)
The two electrophilic Vilsmeier - Haack reagents POCl3·DMF 2 or (CF3SO2)2O·DMF 3 mediate the one-step and selective conversion of O-triethylsilyl (O-TES), O-tert-butyldimethylsilyl (O-TBDMS), O-tert-butyldiphenylsilyl (O-TBDPS), and O-triisopropylsilyl (O-TIPS) ethers of D-glucal to the corresponding C(6)-O-formates.
Concise synthesis of 3-O-(2-O-α-D-glucopyranosyl-6-O-acyl-α-D-glucopyranosyl)-1,2-di-O-acyl-sn-g lycerols
Imai, Hiroto,Oishi, Tohru,Kikuchi, Tsukasa,Hirama, Masahiro
, p. 8451 - 8459 (2007/10/03)
A versatile synthetic route to 3-O(2-O-α-D-glucopyranosyl-6-O-acyl-α-D-glucopyranosyl)-1,2-di-O-acyl-sn-gl ycerols, which should provide various acyl derivatives, has been developed. (C) 2000 Elsevier Science Ltd.
