130051-18-2

Basic information

• Product Name: methyl O-(2-acetamido-2-deoxy-beta-glucopyranosyl)-(1-6)-O-alpha-glucopyranosyl-(1-2)-alpha-glucopyranoside
• Synonyms: methyl O-(2-acetamido-2-deoxy-beta-glucopyranosyl)-(1-6)-O-alpha-glucopyranosyl-(1-2)-alpha-glucopyranoside
• CAS NO: 130051-18-2
• Molecular Formula: C21H37NO16
• Molecular Weight: 559.51558
• Mol File: 130051-18-2.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 935.5°Cat760mmHg
• Flash Point: 519.6°C
• Appearance: /
• Density: 1.68g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.645
• CAS DataBase Reference: methyl O-(2-acetamido-2-deoxy-beta-glucopyranosyl)-(1-6)-O-alpha-glucopyranosyl-(1-2)-alpha-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl O-(2-acetamido-2-deoxy-beta-glucopyranosyl)-(1-6)-O-alpha-glucopyranosyl-(1-2)-alpha-glucopyranoside(130051-18-2)
• EPA Substance Registry System: methyl O-(2-acetamido-2-deoxy-beta-glucopyranosyl)-(1-6)-O-alpha-glucopyranosyl-(1-2)-alpha-glucopyranoside(130051-18-2)

Safety Data

• Hazardous Substances Data: 130051-18-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C21H37NO16/c1-7(26)22-21(37-12-3-8(27)13(28)9(4-23)34-12)18(33)15(30)11(6-25)36-20(21,2)38-19-17(32)16(31)14(29)10(5-24)35-19/h8-19,23-25,27-33H,3-6H2,1-2H3,(H,22,26)/t8-,9-,10-,11-,12+,13+,14-,15-,16+,17-,18+,19-,20-,21-/m1/s1

Upstream product

• 130074-04-3 methyl O-(3,4,6-tri-O-acetyl-2-chloroacetamido-2-deoxy-β-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-acetyl-α-D-glucopyranosyl)-(1->2)-3,4,6-tri-O-acetyl-α-glucopyranoside 
• 130074-05-4 methyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-acetyl-α-D-glucopyranosyl)-(1->2)-3,4,6-tri-O-acetyl-α-glucopyranoside 

Relevant articles and documents

Use of the methylsulfenyl cation as an activator for glycosylation reactions with alkyl (aryl) 1-thioglycopyranosides: synthesis of methyl O-(2-acetamido-2- deoxy-beta-D-glucopyranosyl)-(1----6)-O-alpha-D-glucopyranosyl-(1----2) -alpha-D -glucopyranoside, a derivative of the core trisaccharide of E. coli K12.

Methylsulfenyl bromide (MSB) and methylsulfenyl trifluoromethanesulfonate (MST) have been used to prepare 1,2-cis-linked disaccharides. Ethyl (phenyl) 1-thio-beta-D-gluco- and galacto-pyranosides having non-participating (benzyloxy) protecting groups were used as the donors. The alpha beta-ratio of the products depended on the promoter and conditions of reaction. Intimate ion-pairs, formed initially, may be responsible for the steric outcome of the glycosylations. Thus, with ethyl 2,3,4,6-tetra-O-benzyl-alpha-D-mannopyranoside as a donor, moderate quantities of the beta-linked disaccharide could be produced using MSB as the activator. The synthesis of the title trisaccharide glycoside that contains 1,2-cis and 1,2-trans-linkages is described.