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β-C-(hydroxymethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside is a complex organic compound that belongs to the class of carbohydrates, specifically a glycoside. It is a derivative of β-D-glucopyranoside, where the hydroxyl group at the C1 position is replaced by a hydroxymethyl group. The molecule is further modified by the presence of four benzyl groups attached to the hydroxyl groups at the C2, C3, C4, and C6 positions, which protect the hydroxyl groups and increase the compound's stability. This chemical is often used in organic synthesis, particularly in the preparation of complex oligosaccharides and glycoconjugates, due to its ability to serve as a building block for more intricate carbohydrate structures. The benzyl groups can be removed under specific conditions when the desired glycosidic linkages are formed, allowing for the synthesis of a wide range of biologically active compounds.

89064-71-1

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89064-71-1 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 89064-71-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,9,0,6 and 4 respectively; the second part has 2 digits, 7 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 89064-71:
(7*8)+(6*9)+(5*0)+(4*6)+(3*4)+(2*7)+(1*1)=161
161 % 10 = 1
So 89064-71-1 is a valid CAS Registry Number.

89064-71-1Relevant academic research and scientific papers

Highly stereoselective synthesis of aryl/heteroaryl-: C -nucleosides via the merger of photoredox and nickel catalysis

Ma, Yingying,Liu, Shihui,Xi, Yifan,Li, Hongrui,Yang, Kai,Cheng, Zhihao,Wang, Wei,Zhang, Yongqiang

supporting information, p. 14657 - 14660 (2019/12/11)

A photoredox/nickel dual-catalyzed decarboxylative cross-coupling reaction of anomeric ribosyl/deoxyribosyl acids with aryl/heteroaryl bromides has been developed. The reaction proceeds smoothly under visible-light irradiation and features the using of cost-effective and easily handled catalysts and starting materials, which allows the highly stereoselective synthesis of diverse aryl/heteroaryl-C-nucleosides in moderate to high yields.

Stereo- And regioselective hydroboration of 1-exo-methylene pyranoses: Discovery of aryltriazolylmethyl C-galactopyranosides as selective galectin-1 inhibitors

Dahlqvist, Alexander,Furevi, Axel,Warlin, Niklas,Leffler, Hakon,Nilsson, Ulf J.

, p. 1046 - 1060 (2019/06/08)

Galectins are carbohydrate recognition proteins that bind carbohydrates containing galactose and are involved in cell signaling and cellular interactions, involving them in several diseases. We present the synthesis of (aryltriazolyl)methyl galactopyranos

Synthesis of β-C-Glycopyranosyl Aldehydes and 2,6-Anhydro-heptitols

Khatri, Vinod,Kumar, Amit,Singh, Balram,Malhotra, Shashwat,Prasad, Ashok K.

, p. 11169 - 11174 (2015/11/18)

A convenient route has been developed for the diastereoselective synthesis of β-C-glycopyranosyl aldehydes from d-glucose, d-mannose, and d-galactose. The key step in the synthesis of C-glycosyl aldehydes is the aryl driven reductive dehydration on 1-phen

Novel synthesis of oligosaccharides linked with carbamate and urea bonds utilizing modified Curtius rearrangement

Sawada, Daisuke,Sasayama, Shinya,Takahashi, Hideyo,Ikegami, Shiro

, p. 8780 - 8788 (2008/12/23)

We describe a novel synthesis of various carbamate- and urea-linked disaccharides stereospecifically using sugar carboxylic acids and sugar alcohols or sugar amines by the modified Curtius rearrangement. In this reaction, the reactivity of each hydroxyl g

Synthesis of Fluorinated Homo-C-Nucleoside Analogues from New Carbohydrate-Derived Acylsilanes

Chanteau, Frédéric,Plantier-Royon, Richard,Portella, Charles

, p. 512 - 516 (2007/10/03)

Abstract: The stereocontrolled synthesis of new carbohydrate-derived acylsilanes with the silylcarbonyl moiety linked to the anomeric carbon via a methylene group is described. Reaction of these acylsilanes with perfluoroorganometallic reagents followed by treatment with hydrazines or amidines led to new polyfluorinated homo-C-nucleoside analogues, in a one-pot or two-step transformation, respectively.

A Ramberg-Baecklund approach to the synthesis of C-glycosides, C-linked disaccharides, and C-glycosyl amino acids

Paterson, Duncan E.,Griffin, Frank K.,Alcaraz, Marie-Lyne,Taylor, Richard J. K.

, p. 1323 - 1336 (2007/10/03)

Synthetic applications of exo-glycals, derived from S-glycoside dioxides using the Meyers variant of the Ramberg-Baecklund rearrangement, are described. These include a formal synthesis of a β-glycosidase inhibitor 12 and an efficient route to spirocyclic glucose derivatives 17 and 18. The synthesis of C-linked disaccharides 24, 31, and 38 and the C-glycosyl amino acid 49 using the Ramberg-Baecklund rearrangement is also reported. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

An access to glycoconjugate libraries through multicomponent reactions

Lockhoff, Oswald

, p. 3436 - 3439 (2007/10/03)

Four-component reactions: The Ugi reaction of four suitably functionalized carbohydrate derivatives (as a per-O-benzylated amine, an aldehyde, a carboxylic acid, and an isocyanide) allow the effective assembly of diverse compound libraries. The complex gl

Deoxy-nitrosugars. Stereoelectronic Control in the Reductive Denitration of Tertiary Nitro Ethers. A Synthesis of 'C-Glycosides'

Baumberger, Franz,Vasella, Andrea

, p. 2210 - 2222 (2007/10/02)

The separate, radical denitration with Bu3SnH of the pyranose derivatives 3, 4, 9, and 10 gave in good yields exclusively the 'C-glycosides' 5 and 11, respectively (Scheme 1).Similar reduction of the cylohexyl derivatives 15, 16, 19 and 20 gave 4:1 mixtures of 17, 18, 21 and 22, respectively, always with predominant formation of an axial C,H-bond.In the furanose series a divergent behaviour was observed for the D-mannose-derived nitro ethers 25 and 27 and the D-ribose-derived nitro ethers 30 and 31, respectively, in that the former two gave isomerically homogeneous reduction products (26 and 28, respectively; Scheme 3) and the latter a 1:1 mixture of the diastereoisomers 32 and 33 (Scheme 4).The stereochemical results were explained on the basis of the stereoelectronic effect of the ring O-atom, the preferred conformation of the intermediate, pyramidal alkoxyalkyl radicals and steric effects in the trioxabicyclooctane ring system.

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