187022-49-7

Basic information

• Product Name: Phenyl 3,4,6-Tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxyformamido)-beta-D-glucopyranoside
• Synonyms: Phenyl 3,4,6-Tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxyformamido)-beta-D-glucopyranoside;Phenyl 3,4,6-Tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxyforMaMido)-β-D-glucopyranoside;Phenyl 3,4,6-Tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxyformamido)-βPhenyl 3,4,6-Tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside;(2R,3S,4R,5R,6S)-2-(Acetoxymethyl)-6-(phenylthio)-5-(((2,2,2-trichloroethoxy)carbonyl)amino)tetrahydro-2H-pyran-3,4-diyl diacetate;Phenyl 3,4,6-Tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxyformamido)-b-D-glucopyranoside, 98%
• CAS NO: 187022-49-7
• Molecular Formula: C₂₁H₂₄Cl₃NO₉S
• Molecular Weight: 572.84056
• Mol File: 187022-49-7.mol
• Article Data: 8

Chemical Properties

• Melting Point: 143°C(lit.)
• Boiling Point: 633.127°C at 760 mmHg
• Flash Point: 336.703°C
• Appearance: /
• Density: 1.457g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.572
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Phenyl 3,4,6-Tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxyformamido)-beta-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Phenyl 3,4,6-Tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxyformamido)-beta-D-glucopyranoside(187022-49-7)
• EPA Substance Registry System: Phenyl 3,4,6-Tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxyformamido)-beta-D-glucopyranoside(187022-49-7)

Safety Data

• Hazardous Substances Data: 187022-49-7(Hazardous Substances Data)

Usage

General Description

Phenyl 3,4,6-Tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxyformamido)-beta-D-glucopyranoside is a complex chemical compound with multiple functional groups. It is an acetylated derivative of 2-deoxyglucose with a thioether linkage and a trichloroethoxyformamido group. Phenyl 3,4,6-Tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxyformamido)-beta-D-glucopyranoside is commonly used in biochemistry and organic chemistry research as a synthetic intermediate for the modification of carbohydrates. Its unique structure makes it a valuable tool for studying glycosylation and other cellular processes. Additionally, it has potential applications in pharmaceutical research for the development of novel drugs and therapies.

InChI:InChI=1/C21H24Cl3NO9S/c1-11(26)30-9-15-17(32-12(2)27)18(33-13(3)28)16(25-20(29)31-10-21(22,23)24)19(34-15)35-14-7-5-4-6-8-14/h4-8,15-19H,9-10H2,1-3H3,(H,25,29)/t15-,16-,17+,18+,19-/m0/s1

Upstream product

• 108-98-5 thiophenol 
• 187022-27-1 4-methoxyphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside 
• 172490-46-9 2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 676227-82-0 ((2S,4aR,6S,7R,8R,8aS)-7-Azido-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-tert-butyl-dimethyl-silane 
• 819798-40-8 phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside 
• 148416-94-8 phenyl-3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thio-β-D-galactopyranoside 
• 819798-39-5 phenyl-2-azido-2-deoxy-1-thio-β-D-galactopyranoside 
• 675876-42-3 (2S,3R,4R,5R,6R)-3-Azido-5-benzyloxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-4-ol 
• 136945-14-7 O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl] trichloroacetimidate 
• 108-24-7 acetic anhydride 
• 17341-93-4 2,2,2-Trichloroethyl chloroformate 
• 122210-01-9 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose 
• 122210-05-3 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranose 

Downstream Products

• 1138123-66-6 phenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside S-oxide 
• 133940-44-0 benzyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside 
• 130259-50-6 cyclohexyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside 
• 206751-91-9 benzyl 2-acetamido-2-deoxy-3,6-di-O-pivaloyl-β-D-glucopyranoside 
• 1055335-23-3 benzyl 2-deoxy-2-(2,2,2-trichloroethoxy)carbonylamino-β-D-glucopyranoside 

Relevant articles and documents

Synthesis of LewisX-O-Core-1 threonine: A building block for O-linked LewisX glycopeptides

LewisX (LeX) is a branched trisaccharide Galβ1→4(Fucα1→3)GlcNAc that is expressed on many cell surface glycoproteins and plays critical roles in innate and adaptive immune responses. However, efficient synthesis of glycopeptides bearing LeX remains a major limitation for structure-function studies of the LeX determinant. Here we report a total synthesis of a LeX pentasaccharide 1 using a regioselective 1-benzenesulfinyl piperidine/triflic anhydride promoted [3 + 2] glycosylation. The presence of an Fmoc-threonine amino acid facilitates incorporation of the pentasaccharide in solid phase peptide synthesis, providing a route to diverse O-linked LeX glycopeptides. The described approach is broadly applicable to the synthesis of a variety of complex glycopeptides containing O-linked LeX or sialyl LewisX (sLeX).

Protecting group-free glycoligation by the desulfurative rearrangement of allylic disulfides as a means of assembly of oligosaccharide mimetics

2-(2-Pyridyldithio-3-butenyl) glycosides react with carbohydrate-based thiols in a two-step process involving sulfenyl transfer followed by desulfurative 2,3-allylic rearrangement, promoted by either triphenylphosphine or silver nitrate, to give novel saccharide mimetics. In an alternative embodiment of the same chemistry anomeric thiols are coupled with carbohydrates derivatized in the form of 2-(2-pyridyldithio-3-butenyl) ethers. This new method of glycoligation does not require protection of hydroxyl groups and is compatible with the presence of acetamides, azides, trichloroethoxycarbamates, and thioglycosides. Variations on the general theme enable the preparation of mimetics of reducing and nonreducing oligosaccharides as well as of nonglycosidically linked systems.

Efficient synthesis of core 2 class glycosyl amino acids by one-pot glycosylation approach

We describe the one-pot synthesis of core 2 class branched oligosaccharides initiated by chemo-selective glycosylation of silyl ether. Glycosylation of 6-O-silyl-4-benzyl-2-azido-thiogalactoside with glycosyl fluoride provided selectively 6-glycosylated thioglycoside without both O-glycosylation at the 3 position and S-glycosylation. Subsequent coupling of galactosyl fluoride and amino acids afforded the protected branched oligosaccharides in good yields.