87190-67-8

Basic information

• Product Name: 3,4,6-Tri-O-acetyl-2-deoxy-2-phthaliMido-beta-D-glucopyranosyl 2,2,2-TrichloroacetiMidate
• Synonyms: 3,4,6-Tri-O-acetyl-2-deoxy-2-phthaliMido-beta-D-glucopyranosyl 2,2,2-TrichloroacetiMidate;3,4,6-Tri-O-acetyl-2-deoxy-2-phthaliMido-β-D-glucopyranosyl 2,2,2-TrichloroacetiMidate
• CAS NO: 87190-67-8
• Molecular Formula: C₂₂H₂₁Cl₃N₂O₁₀
• Molecular Weight: 579.76854
• Mol File: 87190-67-8.mol
• Article Data: 4

Chemical Properties

• Melting Point: 146°C(lit.)
• Boiling Point: 596.073°C at 760 mmHg
• Flash Point: 314.294°C
• Appearance: /
• Density: 1.62g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.629
• CAS DataBase Reference: 3,4,6-Tri-O-acetyl-2-deoxy-2-phthaliMido-beta-D-glucopyranosyl 2,2,2-TrichloroacetiMidate(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,6-Tri-O-acetyl-2-deoxy-2-phthaliMido-beta-D-glucopyranosyl 2,2,2-TrichloroacetiMidate(87190-67-8)
• EPA Substance Registry System: 3,4,6-Tri-O-acetyl-2-deoxy-2-phthaliMido-beta-D-glucopyranosyl 2,2,2-TrichloroacetiMidate(87190-67-8)

Safety Data

• Hazardous Substances Data: 87190-67-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C22H21Cl3N2O10/c1-9(28)33-8-14-16(34-10(2)29)17(35-11(3)30)15(20(36-14)37-21(26)22(23,24)25)27-18(31)12-6-4-5-7-13(12)19(27)32/h4-7,14-17,20,26H,8H2,1-3H3/t14-,15-,16+,17+,20-/m0/s1

Upstream product

• 85-44-9 phthalic anhydride 

Downstream Products

• 125085-02-1 methyl 2-O-benzyl-6-deoxy-4-O-methyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-β-D-galactopyranoside 
• 87190-69-0 tert-Butyldimethylsilyl-O-(3,4,6-tri-O-acetyl-2-desoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2-azido-4,6-O-benzyliden-2-desoxy-β-D-galactopyranosid 
• 144382-53-6 2-O-benzyl-N-benzyloxycarbonyl-3-O-(benzyloxycarbonylmethyl)-6 O-(tert-butyldimethylsilyl)-1,5-dideoxy-1,5-imino-4-O-(3',4',6'-tri-O-acetyl-2'-deoxy-2'-phthalimido-β-D-glucopyranosyl)-D-mannitol 
• 108282-44-6 methyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phtalimido-β-D-glucopyranosyl)-(1-3)-O-<(3,4,6-tri-O-acetyl-2-deoxy-2-phtalimido-β-D-glucopyranosyl)-(1-6)>-O-(2-O-benzoyl-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside 
• 108256-96-8 methyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phtalimido-β-D-glucopyranosyl)-(1-3)-O-(2-O-benzoyl-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside 
• 153984-86-2 4-methoxyphenyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1<*>4)-6-O-levulinoyl-2,3-di-O-p-toluoyl-β-D-glucopyranoside 
• 63000-71-5 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucal 
• 195976-19-3 methyl O-(3',4',6'-tri-O-acetyl-2'-deoxy-2'-phthalimido-β-D-glucopyranosyl)-(1'->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside 
• 80859-31-0 benzyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->2)-O-[(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->6)]-3,4-di-O-benzyl-α-D-mannopyranoside 
• 210347-94-7 4-methoxybenzyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-O-(4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-O-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 107855-12-9 benzyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 

Relevant articles and documents

Asymmetric Total Synthesis of Brasilicardins

Brasilicardins, bacterial diterpenoid natural products that display highly potent immunosuppressive activity, are promising immunosuppressant drug candidates. Structurally, they can be described as hybrids of terpenoids, amino acids, and saccharides, and share a characteristic highly strained anti-syn-anti-fused perhydrophenanthrene terpenoid scaffold (ABC-ring system) with two quaternary asymmetric carbon atoms. A unified and stereoselective total synthesis of all four brasilicardins has been designed based on the strategic use of an intramolecular conjugate addition. The ABC-ring system was initially constructed with high stereocontrol by novel intramolecular conjugate additions of Weinreb amides and in situ generated (Z)-vinyl copper species. The late-stage common intermediate was subjected to stereoselective installation of the amino acid component, followed by introduction of the saccharide unit via glycosylation to accomplish the total synthesis of brasilicardins A–D. Our synthesis offers opportunities to synthesize various brasilicardin analogues for biological and pharmacological investigations.

Solid-phase synthesis of thioether-linked glycopeptide mimics for application to glycoprotein semisynthesis.

[reaction: see text]. Glycoproteins are particularly suited to protein semisynthesis since homogeneous samples for biological analyses are not readily available using traditional recombinant techniques. Here we apply glycosyl iodoacetamides, normally used for the modification of bacterially derived proteins, to solid-phase glycopeptide synthesis. This provides access to glycopeptide alpha-thioesters, which may lend themselves to the semisynthesis of homogeneous N-linked glycoprotein mimics and novel glycopeptide libraries.