22551-65-1 Usage
Chemical class
Disaccharide
It is a compound formed by the condensation of two monosaccharide units.
Parent compound
Glucopyranoside
It is a derivative of glucopyranoside, which is a six-carbon sugar (monosaccharide) with a pyranose ring structure.
Stereochemistry
a-D-glucopyranoside
The compound has an alpha (a) configuration, meaning the glycosidic bond is formed on the upper side of the ring when drawn in the Haworth projection.
Acetylation
Tetra-O-acetyl
Four hydroxyl (-OH) groups in the molecule are substituted with acetyl groups (-OCOCH3), which increases its reactivity and stability.
Additional acetylation
2,3,4,6-tetra-O-acetyl-b-D-glucopyranosyl
The second monosaccharide unit in the disaccharide is also a glucopyranoside, but with four acetyl groups attached at the 2, 3, 4, and 6 positions.
Functional groups
Acetyl groups
The presence of multiple acetyl groups provides the compound with unique reactivity and properties, making it useful in organic synthesis.
Application
Synthesis of complex carbohydrates
It serves as an important intermediate in the synthesis of complex carbohydrates, which are essential components of many biological molecules.
Field of use
Organic chemistry and biochemistry
The compound is commonly used in these fields due to its unique properties and reactivity.
Structural importance
Studying sugar and carbohydrate behavior
Its precise chemical structure and properties make it a valuable tool for understanding the behavior of sugars and carbohydrates in various biological and chemical processes.
Solubility
Soluble in organic solvents
The compound is likely to be soluble in organic solvents such as chloroform, methanol, or acetone, which is useful for its manipulation and analysis in the laboratory.
Check Digit Verification of cas no
The CAS Registry Mumber 22551-65-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,2,5,5 and 1 respectively; the second part has 2 digits, 6 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 22551-65:
(7*2)+(6*2)+(5*5)+(4*5)+(3*1)+(2*6)+(1*5)=91
91 % 10 = 1
So 22551-65-1 is a valid CAS Registry Number.
InChI:InChI=1/C28H38O19/c1-11(29)37-9-19-21(39-13(3)31)23(41-15(5)33)25(42-16(6)34)28(46-19)47-24-22(40-14(4)32)20(10-38-12(2)30)45-27(44-18(8)36)26(24)43-17(7)35/h19-28H,9-10H2,1-8H3/t19-,20-,21-,22-,23+,24+,25-,26-,27-,28+/m1/s1
22551-65-1Relevant articles and documents
The Glc2Man2-fragment of the N-glycan precursor - A novel ligand for the glycan-binding protein malectin?
Mueller, Lisa N.,Muhle-Goll, Claudia,Biskup, Moritz B.
supporting information; experimental part, p. 3294 - 3299 (2010/08/21)
The Glcα(1→3)Glcα(1→3)Manα(1→2)Man tetrasaccharide (Glc2Man2-fragment), a substructure of the natural N-glycan precursor, was synthesized. The interaction of this fragment with the protein malectin, a carbohydrate binding protein localized in the endoplasmatic reticulum, was investigated by 1H15N HSQC experiments and isothermal calorimetry. The chemical shift perturbations of nuclei in the protein's backbone caused by the binding of the Glc 2Man2-fragment to malectin suggest a binding mode like the known ligand nigerose. The Royal Society of Chemistry 2010.
Peracetylated laminaribiose: Preparation by specific degradation of curdlan and its chemical conversion into N-acetylhyalobiuronic acid
Wang,Sakairi,Kuzuhara
, p. 133 - 148 (2007/10/02)
β-Laminaribiose octaacetate (2b) was prepared in greater than 50% yield from the microbial polysaccharide curdlan by specific degradation with a yeast cell-wall lytic enzyme preparation, Kitalase, and subsequent acetylation. Acetolysis of curdlan also gav
THE EFFECT OF HIGH PRESSURE ON THE STEREOSPECIFICITY OF THE GLYCOSYLATION REACTION
Kochetkov, Nikolay K.,Zhulin, Victor M.,Klimov, Evgeny M.,Malysheva, Nelly N.,Makarova, Zinaida G.,Ott, Andrej Ya
, p. 241 - 254 (2007/10/02)
At a pressure of 1,4 GPa and room temperature, the glycosylation of trityl ethers by 1,2-O-cyanoethylidene derivatives of sugars, and the polycondensation of the proper monomers in dichloromethane, proceed with absolute stereospecificity, giving rise to a
