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147157-97-9

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147157-97-9 Usage

General Description

2-Deoxy-2-phthalimido-3,4,6-tri-O-acetyl-alpha-D-glucopyranosyl fluoride is a chemical compound used in organic synthesis and biochemistry research. It is a derivative of glucose, in which the hydroxyl group at the 2-position has been replaced by a phthalimido group and the 3, 4, and 6 hydroxyl groups have been acetylated. 2-DEOXY-2-PHTHALIMIDO-3,4,6-TRI-O-ACETYL-ALPHA-D-GLUCOPYRANOSYL FLUORIDE is commonly used as a glycosyl donor in the synthesis of oligosaccharides and glycoconjugates. It is also utilized as a substrate in enzymatic assays to study the activity of glycosidases and glycosyltransferases. Additionally, this compound has potential applications in medicinal chemistry for the development of glycoside-based drugs.

Check Digit Verification of cas no

The CAS Registry Mumber 147157-97-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,4,7,1,5 and 7 respectively; the second part has 2 digits, 9 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 147157-97:
(8*1)+(7*4)+(6*7)+(5*1)+(4*5)+(3*7)+(2*9)+(1*7)=149
149 % 10 = 9
So 147157-97-9 is a valid CAS Registry Number.
InChI:InChI=1/C20H20FNO9/c1-9(23)28-8-14-16(29-10(2)24)17(30-11(3)25)15(18(21)31-14)22-19(26)12-6-4-5-7-13(12)20(22)27/h4-7,14-18H,8H2,1-3H3/t14-,15-,16-,17-,18+/m1/s1

147157-97-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name [(2R,3S,4R,5R,6R)-3,4-diacetyloxy-5-(1,3-dioxoisoindol-2-yl)-6-fluorooxan-2-yl]methyl acetate

1.2 Other means of identification

Product number -
Other names 2-Deoxy-2-phthalimido-3,4,6-tri-O-acetyl-|A-D-glucopyranosyl fluoride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:147157-97-9 SDS

147157-97-9Relevant articles and documents

Synthesis of glycosyl fluorides from (phenylthio)glycosides using IF5-pyridine-HF

Kunigami, Masataka,Hara, Shoji

, p. 78 - 80 (2015/10/20)

IF5-pyridine-HF, an air- and moisture-stable fluorinating reagent, was applied to the synthesis of glycosyl fluorides from (phenylthio)glycosides. Common protecting groups of alcohol and diol can tolerate the reaction conditions performed, and therefore, the present method is applicable to the synthesis of various glycosyl fluorides.

Preparation of glucosaminyl muramic acid derivatives

-

, (2008/06/13)

The present invention provides a method for the preparation of disaccharides, such as glucosaminyl muramic acids peptides and derivatives. The method includes condensing a protected muramic acid ester with a 1-organothio- or 1-fluoroglucosamine derivative in the presence of a suitable promoter to produce a protected glucosaminyl muramic acid ester. The protected glucosaminyl muramic acid ester may be used to prepare disaccharide peptides, such as N-acetylglucosaminyl-N-acetylmuramyl dipeptides, which have demonstrated immunological activity. Protected muramic acid esters and 1-organothio- or 1-fluoro- glucosamine compounds which may be employed as intermediates in the method are also provided.

A new method of anomeric protection and activation based on the conversion of glycosyl azides into glycosyl fluorides

Broder,Kunz

, p. 221 - 241 (2007/10/02)

Glycosyl azides provide reliable anomeric protection stable to conditions for hydrolytic removal of ester groups, for reductive opening or release of acetalic diol protection, for the introduction of ether-type protection, and for glycosylation processes. The utility of this anomeric protection is further enhanced as glycosyl azides may be converted into glycosyl fluorides, which can be activated for glycosylation reactions. To this end, glycosyl azides have been subjected to 1,3-dipolar cycloaddition with di-tert-butyl acetylenedicarboxylate. On treatment with hydrogen fluoride-pyridine complex the N-glycosyl triazole derivatives directly give glycosyl fluorides. Glycosyl azides provide reliable anomeric protection stable to conditions for hydrolytic removal of ester groups, for reductive opening or release of acetalic idol protection, for the introduction of ether-type protection, and for glycosylation processes. The utility of this anomeric protection is further enhanced as glycosyl azides may be converted into glycosyl fluorides, which can be activated for glycosylation reactions. To this end, glycosyl azides have been subjected to 1,3-dipolar cycloaddition with di-tert-butyl acetylenedicarboxylate. On treatment with hydrogen fluoride-pyridine complex the N-glycosyl triazole derivatives directly give glycosyl fluorides.

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