87508-17-6

Basic information

• Product Name: PHENYL 4,6-O-BENZYLIDENE-1-THIO-BETA-D-GLUCOPYRANOSIDE
• Synonyms: PHENYL 4,6-O-BENZYLIDENE-1-THIO-BETA-D-GLUCOPYRANOSIDE;Phenyl 4,6-O-Benzylidene-1-thio-β-D-glucopyranoside;Phenyl 4,6-O-Benzylidene-1-thio-&beta
• CAS NO: 87508-17-6
• Molecular Formula: C₁₉H₂₀O₅S
• Molecular Weight: 360.42
• Product Categories: Glycosyl Donors;Biochemistry;Glucose;Sugars;Thioglycosides
• Mol File: 87508-17-6.mol
• Article Data: 41

Chemical Properties

• Melting Point: 185 °C
• Boiling Point: 581.153 °C at 760 mmHg
• Flash Point: 305.271 °C
• Appearance: /
• Density: 1.397 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: -45.5 ° (C=1, CHCl3)
• Storage Temp.: Freezer
• Solubility: slightly sol. in Chloroform
• CAS DataBase Reference: PHENYL 4,6-O-BENZYLIDENE-1-THIO-BETA-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: PHENYL 4,6-O-BENZYLIDENE-1-THIO-BETA-D-GLUCOPYRANOSIDE(87508-17-6)
• EPA Substance Registry System: PHENYL 4,6-O-BENZYLIDENE-1-THIO-BETA-D-GLUCOPYRANOSIDE(87508-17-6)

Safety Data

• Hazardous Substances Data: 87508-17-6(Hazardous Substances Data)

Usage

Uses

This is a protected glucopyranoside useful as a building block for synthesis of complex carbohydrates. The compound has β-phenylthio and 4,6-benzylidene protecting groups.

InChI:InChI=1/C19H20O5S/c20-15-16(21)19(25-13-9-5-2-6-10-13)23-14-11-22-18(24-17(14)15)12-7-3-1-4-8-12/h1-10,14-21H,11H2/t14-,15-,16-,17-,18?,19+/m1/s1

Upstream product

• 16758-34-2 1-thiophenyl-β-D-galactopyranoside 
• 100-52-7 benzaldehyde 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 1203546-87-5 phenyl 2-O-acetyl-3-O-(azulen-1-yl-oxo-acetyl)-4,6-O-benzylidene-β-D-thiogalactopyranoside 
• 108-98-5 thiophenol 
• 4163-60-4 β-D-galactose peracetate 
• 2280-44-6 D-Glucose 
• 1203546-81-9 phenyl 3-O-(azulen-1-yl-oxo-acetyl)-4,6-O-benzylidene-β-D-thioglucopyranoside 
• 13992-16-0 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α,β-D-glucopyranoside 
• 13992-15-9 phenyl-1-thio-α-D-glucopyranoside 
• 604-68-2 α-D-glucopyranose peracetylate 
• 13992-16-0 Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester 
• 13992-16-0 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 128848-51-1 phenyl 3-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside 

Downstream Products

• 128848-54-4 phenyl 4,6-O-benzylidene-2,3-di-O-trimethylsilyl-1-thio-β-D-galactopyranoside 
• 128848-45-3 phenyl 4,6-O-benzylidene-2,3-di-O-trimethylsilyl-1-thio-β-D-glucopyranoside 
• 87470-70-0 S-phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thia-α-D-glucopyranoside 
• 124477-09-4 Dithiocarbonic acid O-((2S,4aR,6S,7R,8S,8aS)-8-benzyloxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl) ester S-methyl ester 
• 190367-07-8 phenyl 4,6-O-benzylidene-2,3-di-O-benzoyl-1-thio-β-D-glucopyranoside 
• 201056-61-3 phenyl 2-O-acetyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 260779-95-1 phenyl 2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 161391-28-2 phenyl 4,6-O-benzylidene-2,3-di-O-methyl-1-thio-β-D-glucopyranose 
• 322472-69-5 phenyl 4,6-O-benzylidene-2-O-methyl-1-thio-β-D-glucopyranose 
• 87470-72-2 phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside 
• 124477-08-3 phenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside 
• 208644-75-1 phenyl 2,3-di-O-benzoyl-4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside 
• 213997-89-8 phenyl 3-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside 
• 804566-04-9 phenyl 2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside 

Relevant articles and documents

N -Glycosylation with sulfoxide donors for the synthesis of peptidonucleosides

The synthesis of glycopyranosyl nucleosides modified in the sugar moiety has been less frequently explored, notably because of the lack of a reliable method to glycosylate pyrimidine bases. Herein we report a solution in the context of the synthesis of peptidonucleosides. They were obtained after glycosylation of different pyrimidine nucleobases with glucopyranosyl donors carrying an azide group at the C4 position. A methodological study involving different anomeric leaving groups (acetate, phenylsulfoxide and ortho-hexynylbenzoate) showed that a sulfoxide donor in combination with trimethylsilyl triflate as the promoter led to the best yields.

Studies towards the total synthesis of repeating unit of O-sulfated polysaccharide from marine bacterium Cobetia pacifica KMM 3878

Herein we report assembly of the appropriately protected trisaccharide repeating unit of Cobetia pacifica KMM 3878 O-sulfated polysaccharide. Our synthesis involves 3,4-O-pyruvilated galactose as the key building block which acts as a donor as well as acceptor in the construction of trisaccharide. We obtained the R isomer as a major stereoisomer in the pyruvilation reaction. The glycosylations proceeded with high stereo and regioselectivity.

Conformationally Switchable Glycosyl Donors

Glycosyl donors functionalized with 2,2′-bipyridine moieties on the 3-OH and 6-OH or the 2-OH and 4-OH undergo a conformational change when forming 1:1 complexes with Zn2+ ions. The pyranoside ring of the zinc complexes adopted axial-rich skew boat conformations. The reactivities of the two glycosyl donors were investigated by performing a series of glycosylations in the presence or absence of Zn2+ ions. These glycosylations suggested a decrease in reactivity when binding Zn2+. The conformational effect of binding Zn2+ was therefore studied using a third glycosyl donor, unable to undergo conformational changes when binding Zn2+. From competition experiments, it was observed that the binding-induced conformational change increased the reactivity slightly compared to the glycosyl donor unable to undergo a conformational change.