211621-55-5Relevant academic research and scientific papers
Nitro-polyols via pyridine promoted C=C cleavage of 2-nitroglycals. Application to the synthesis of (-)-hyacinthacine A1
Tang, Shengbiao,Xiong, De-Cai,Jiang, Shende,Ye, Xin-Shan
, p. 568 - 571 (2016)
A mild and convenient transformation for the synthesis of nitro-polyols is described. The nitro-polyol derivatives were prepared either from 2-nitroglycals via a pyridine-promoted scission of the carbon-carbon double bond or from glycals via a sequential
2-nitroglycal and efficient synthesis method thereof
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Paragraph 0047-0050, (2021/08/06)
The invention discloses an efficient synthesis method of 2-nitroglycal, and belongs to the technical field of synthesis of sugar. The structure of the 2-nitroglycal is shown in the specification. Secondly, the invention also provides a preparation method of the 2-nitro saccharide alkene, and the preparation method provided by the invention can be used for efficiently preparing the 2-nitroglycal through one-step synthesis.
Synthesis of 2-nitroglycals from glycals using the tetrabutylammonium nitrate-trifluoroacetic anhydride-triethylamine reagent system and base-catalyzed ferrier rearrangement of acetylated 2-nitroglycals
Dharuman, Suresh,Gupta, Preeti,Kancharla, Pavan K.,Vankar, Yashwant D.
, p. 8442 - 8450 (2013/09/24)
A reagent system comprising tetrabutylammonium nitrate-trifluoroacetic anhydride-triethylamine has been developed for the synthesis of 2-nitroglycals from various protected glycals. The base-catalyzed Ferrier rearrangement on tri-O-acetylated 2-nitroglycals has been reported for the first time. Reactivity of these nitroacetates and associated selectivity has been examined, and some of the products have been converted into 2,3-diamino-2,3-dideoxyglycosides and methyl N-acetyl-d-lividosaminide.
N-heterocyclic carbene catalyzed C-glycosylation: A concise approach from stetter reaction
Vedachalam, Seenuvasan,Tan, Shi Min,Teo, Hui Ping,Cai, Shuting,Liu, Xue-Wei
supporting information; experimental part, p. 174 - 177 (2012/02/16)
Described herein is the first example of an organocatalytic approach for acylanion addition to the anomeric carbon of 2-nitroglucal using an N-heterocyclic carbene catalyst. Control over the reaction conditions gives β-selective and nitro-eliminated C-glycosides, providing opportunities to produce new classes of C-glycoside.
Acetyl chloride - Silver nitrate - Acetonitrile: A reagent system for the synthesis of 2-nitroglycals and 2-nitro-1-acetamido sugars from glycals
Kancharla, Pavan K.,Reddy, Y. Suman,Dharuman, Suresh,Vankar, Yashwant D.
experimental part, p. 5832 - 5837 (2011/09/20)
A new reagent system comprising acetyl chloride, silver nitrate, and acetonitrile has been developed for the synthesis of 2-nitroglycals from the corresponding glycals. Under certain conditions, the formation of 2-nitro-1-acetamido sugars has also been observed. In addition, a few other non-carbohydrate-derived olefins also gave the corrresponding conjugated nitroolefins.
A novel and efficient route towards α-GalNAc-Ser and α-GalNAc-Thr building blocks for glycopeptide synthesis
Winterfeld, Gottfried A.,Ito, Yukishige,Ogawa, Tomoya,Schmidt, Richard R.
, p. 1167 - 1171 (2007/10/03)
Michael addition of serine and threonine derivatives 4a-4c to 3,4,6-tri- O-benzyl-2-nitro-D-galactal (1) afforded the corresponding 2-deoxy-2-nitro- α-D-galactopyranosides 5a-5c in good yield and stereoselectivity. 2-deoxy-2- nitroglycosides 5a and 5b were reduced to the 2-acetamido compounds by platinized Raney nickel T4. Manipulation of the protecting groups afforded known N-Fmoc-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D- galactopyranosyl)-L-serine (8a) and -threonine (8b), valuable building blocks for O-glycopeptide synthesis.
Convenient glycoside synthesis of amino sugars: Michael-type addition to 2-nitro-D-galactal
Das, Jagattaran,Schmidt, Richard R.
, p. 1609 - 1613 (2007/10/03)
Formation of 3,4,6-tri-O-benzyl-2-nitro-D-galactal (3) was readily accomplished starting from tri-O-benzyl-D-galactal (1) by acetyl nitrate addition to 2 and base-promoted acetic acid elimination. Addition of alcohols to 3 under conditions of base catalysis afforded 2-deoxy-2-nitrogalactopyranosides 4a-e in high yields; high α-selectivity was obtained with strong bases, whereas weaker bases furnished mainly the corresponding β-galactopyranosides. Chemoselective nitro group reduction in these glycosides was successfully carried out in the case of disaccharide 4cα using Raney nickel as catalyst, thereby affording after N-acetylation the corresponding 2-acetylamino-2-deoxy derivative 5cα.
