197144-02-8

Basic information

• Product Name: 2,3,4-tri-O-acetyl-D-xylopyranosyl trichloroacetimidate
• Synonyms: 2,3,4-tri-O-acetyl-D-xylopyranosyl trichloroacetimidate
• CAS NO: 197144-02-8
• Molecular Weight: 420.631
• Mol File: 197144-02-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2,3,4-tri-O-acetyl-D-xylopyranosyl trichloroacetimidate(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4-tri-O-acetyl-D-xylopyranosyl trichloroacetimidate(197144-02-8)
• EPA Substance Registry System: 2,3,4-tri-O-acetyl-D-xylopyranosyl trichloroacetimidate(197144-02-8)

Safety Data

• Hazardous Substances Data: 197144-02-8(Hazardous Substances Data)

Upstream product

• 106820-14-8 2,3,4-Tri-O-acetyl-D-xylopyranose 
• 545-06-2 trichloroacetonitrile 
• 87-72-9 D-Xylose 
• 3068-31-3 1-bromo-2,3,4-tri-O-acetyl-α-D-xylopyranose 
• 197143-93-4 Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester 
• 62446-93-9 1,2,3,4-tetra-O-acetyl-D-xylopyranose 

Downstream Products

• 197144-03-9 Benzoic acid (E)-(R)-1-[(S)-1-azido-2-((2R,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-ethyl]-hexadec-2-enyl ester 
• 6734-33-4 4-methylumbellifer-7-yl β-D-xylopyranoside 
• 1253227-71-2 4'-acetoxy-6-C-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-7-benzyloxy-5-hydroxyflavan 
• 1253227-87-0 4'-acetoxy-6-C-(tri-O-acetyl-α-L-arabinopyranosyl)-8-C-(tri-O-acetyl-β-D-xylopyranosyl)-5,7-dihydroxyflavan 
• 1253227-85-8 4'-acetoxy-6-C-(2,3,4-tri-O-acetyl-α-D-arabinopyranosyl)-8-C-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-5,7-dihydroxyflavan 
• 1253227-81-4 4'-acetoxy-6,8-di-C-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-5,7-dihydroxyflavan 
• 1253227-78-9 4'-acetoxy-6-C-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-8-C-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-5,7-dihydroxyflavan 
• 197144-04-0 Benzoic acid (E)-(R)-1-[(S)-1-octadecanoylamino-2-((2R,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-ethyl]-hexadec-2-enyl ester 
• 889129-11-7 3β-O-[(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->3)-4,6-O-benzylidene-2-O-levulinoyl-β-D-glucopyranosyl]cholesterol 
• 889129-10-6 ethyl (2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->3)-4,6-O-benzylidene-2-O-levulinoyl-1-thio-β-D-glucopyranoside 

Relevant articles and documents

Glycosyl coumarin carbonic anhydrase IX and XII inhibitors strongly attenuate the growth of primary breast tumors

A series of 7-substituted coumarins incorporating various glycosyl moieties were synthesized and investigated for the inhibition of the zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1). These coumarins were very weak or ineffective as inhibitors of the housekeeping, offtarget isoforms CA I and II, but some of them inhibited tumor-associated CA IX and XII in the low nanomolar range. They also significantly inhibited the growth of primary tumors by the highly aggressive 4T1 syngeneic mouse mammary tumor cells at 30 mg/kg, constituting interesting candidates for the development of conceptually novel anticancer drugs. Because CA IX is overexpressed in hypoxic tumors and exhibits very limited expression in normal tissues, such compounds may be useful for treating cancers not responsive to classic chemo- and radiotherapy.

Novel xylosidesurfactant

The invention belongs to the technical field of surfactants for fine chemistry and discloses a novel sugar-based surfactant, namely, alkoxyethyl-beta-D-xylopyranoside in order to solve the problem of limitation to application of traditional alkyl glycoside as the surfactant due to the fact water solubility of traditional alkyl glycoside is gradually reduced with increase of carbon chain length. Compared with traditional alkyl glycoside with the same carbon chain length, the surfactant has better water solubility and surface activity as well as selectable and controllable foaming capacity and emulsifying property. Besides, raw materials for synthesis comprisexylose obtained from waste crop leftovers and naturally-sourced fatty alcohol and have rich sources. The glycoside can be widely applied to application industries such as biochemical engineering, pharmacy, pesticides, food processing, cosmetics, scientific research and the like.

Synthesis of XylβCer, Galβ1-4XylβCer, NeuAcα2-3Galβ1-4XylβCer and the Corresponding Lactone and Lactam Trisaccharides

2-(Trimethylsilyl)ethyl 2-O-benzoyl- and 2,3-di-O-acetyl-β-D-xylopyranosides (12 and 14) were synthesized in high yields and subjected to glycosylation with various glycosyl donors. Galactosylation of 12 gave the xylose analogue of TMSEt lactoside (3), which was transformed into the glycosyl acceptor 19. Sialylation then gave the xylose analogue of GM3 trisaccharide (5). The TMSEt glycosides 10, 25, and 32 were transformed into the corresponding trichloroacetimidates, which were used for glycosylation of an azidosphingosine derivative. The resulting sphingosyl glycosides were transformed into the title ceramides. Treatment of NeuAcα2-3Galβ1-4XylβCer (5) with acetic acid gave the corresponding 1″→2′-lactone 7. Glycosylation of 12 or 14 with a GM4-lactam donor (40) gave the xylose analogue of GM3-lactam (42). There was a 3-fold increase in the formation of GAG chains in the presence of 0.5 μM XylβCer (2) in the medium.