79528-48-6

Basic information

• Product Name: METHYL 3,4,6-TRI-O-ACETYL-2-DEOXY-2-PHTHALIMIDO-1-THIO-BETA-D-GLUCOPYRANOSIDE
• Synonyms: METHYL 3,4,6-TRI-O-ACETYL-2-DEOXY-2-PHTHALIMIDO-1-THIO-BETA-D-GLUCOPYRANOSIDE;METHYL-2-DEOXY-2-PHTHALIMIDO-1-THIO-3,4,6-TRI-O-ACETYL-BETA-D-GLUCOPYRANOSIDE;.beta.-D-Glucopyranoside, methyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-, 3,4,6-triacetate;Methyl 3,4,6-Tri-O-acetyl-2-deoxy-2-phthaliMido-1-thio-β-D-glucopyranoside;Methyl 3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-&beta
• CAS NO: 79528-48-6
• Molecular Formula: C₂₁H₂₃NO₉S
• Molecular Weight: 465.47
• Product Categories: Biochemistry;Glucose;N-Substituted Maleimides, Succinimides & Phthalimides;N-Substituted Phthalimides;Sugars;Thioglycosides
• Mol File: 79528-48-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 150 °C
• Boiling Point: 584.545°C at 760 mmHg
• Flash Point: 307.322°C
• Appearance: /
• Density: 1.413g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 49.5 ° (C=1, CHCl3)
• Storage Temp.: Freezer
• CAS DataBase Reference: METHYL 3,4,6-TRI-O-ACETYL-2-DEOXY-2-PHTHALIMIDO-1-THIO-BETA-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 3,4,6-TRI-O-ACETYL-2-DEOXY-2-PHTHALIMIDO-1-THIO-BETA-D-GLUCOPYRANOSIDE(79528-48-6)
• EPA Substance Registry System: METHYL 3,4,6-TRI-O-ACETYL-2-DEOXY-2-PHTHALIMIDO-1-THIO-BETA-D-GLUCOPYRANOSIDE(79528-48-6)

Safety Data

• Hazardous Substances Data: 79528-48-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C21H23NO9S/c1-10(23)28-9-15-17(29-11(2)24)18(30-12(3)25)16(21(31-15)32-4)22-19(26)13-7-5-6-8-14(13)20(22)27/h5-8,15-18,21H,9H2,1-4H3/t15-,16-,17-,18-,21+/m1/s1

Upstream product

• 10022-13-6 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose 
• 74-93-1 methylthiol 
• 3908-55-2 Trimethyl(methylthio)silane 
• 17314-32-8 tributyl(methylthio)stannane 

Downstream Products

• 110089-11-7 Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-methylsulfanyl-tetrahydro-pyran-4-yl ester 
• 110089-09-3 Methyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 110089-10-6 2-((2S,3R,4R,5S,6R)-6-Benzyloxymethyl-4,5-dihydroxy-2-methylsulfanyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione 
• 118281-97-3 methyl 4-O-<2-acetamido-2-deoxy-4,6-O-(4-methoxybenzylidene)-3-O-<2,4,6-tri-O-benzyl-3-O-(α-L-rhamnopyranosyl)-α-D-galactopyranosyl>-β-D-glucopyranosyl>-2,3-O-isopropylidene-α-L-rhamonpyranoside 
• 118281-95-1 methyl 4-O-<2-acetamido-3-O-(3-O-acetyl-2,4,6-tri-O-benzyl-α-D-galactopyranosyl)-2-deoxy-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl>-2,3-O-isopropylidene-α-L-rhamonpyranoside 
• 118281-96-2 methyl 4-O-<2-acetamido-2-deoxy-4,6-O-(4-methoxybenzylidene)-3-O-(2,4,6-tri-O-benzyl-α-D-galactopyranosyl)-β-D-glucopyranosyl>-2,3-O-isopropylidene-α-L-rhamonpyranoside 
• 118281-89-3 methyl 4-O-<2-acetamido-2-deoxy-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl>-2,3-O-isopropylidene-α-L-rhamonopyranoside 
• 70831-94-6 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranosyl bromide 
• 116730-43-9 benzyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 107855-13-0 benzyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-O-(2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 120424-68-2 C₇₉H₈₅NO₂₁ 
• 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

Iodine and its interhalogen compounds: Versatile reagents in carbohydrate chemistry v. synthesis of 1,2-trans-linked 1-thioglycosides from the per-o-acetylated glycoses

Treatment of per-O-acetylated mono- and di-saccharides with (alkyl/arylthio)trimethylsilane and iodine at ambient temperature results in the formation of the corresponding 1,2-trans-1-thioglycosides in very high yield. In the case of higher boiling thiols such as ethanethiol, the reaction can be effectively carried out in the presence of the thiol itself instead of the silylated derivative, but the reaction is not stereospecific. Moreover, in the latter reactions a portion of the starting material remains unchanged even on prolonged reaction. With β-D-glucose pentaacetate (11) as the starting material, its epimerisation occurred during the reaction and therefore the recovered starting material was of α-D-configuration. In addition, the methyl disulphide-hexamethyldisilane system has been found to serve as an effective and cheaper alternative to the expensive (methylthio)-trimethylsilane.

A NEW, STEREOSELECTIVE SYNTHESIS OF METHYL 1,2-TRANS-1-THIOGLYCOSIDES

Per-O-acetylated glycopyranoses were converted by methylthiotrimethylsilane in the presence of boron trifluoride or trimethylsilyl trifluoromethanesulfonate to the corresponding methyl 1,2-trans-1-thioglycopyranosides in a highly stereoselective process.