150935-65-2

Basic information

• Product Name: a-D-Mannopyranoside, phenyl 1-thio-, 2,3,4-tribenzoate
• Synonyms: a-D-Mannopyranoside, phenyl 1-thio-, 2,3,4-tribenzoate
• CAS NO: 150935-65-2
• Molecular Formula: C₃₃H₂₈O₈S
• Molecular Weight: 584.63562
• Mol File: 150935-65-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: a-D-Mannopyranoside, phenyl 1-thio-, 2,3,4-tribenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: a-D-Mannopyranoside, phenyl 1-thio-, 2,3,4-tribenzoate(150935-65-2)
• EPA Substance Registry System: a-D-Mannopyranoside, phenyl 1-thio-, 2,3,4-tribenzoate(150935-65-2)

Safety Data

• Hazardous Substances Data: 150935-65-2(Hazardous Substances Data)

Upstream product

• 150935-64-1 phenyl 2,3,4-tri-O-benzoyl-6-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside 
• 75-36-5 acetyl chloride 
• 152488-25-0 phenyl 6-O-(tert-butyldimethylsilyloxy)-1-thio-α-D-mannopyranoside 
• 2936-70-1 (2R,3S,4S,5S,6R)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 
• 13992-16-0 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 

Downstream Products

• 262605-41-4 Succinic acid mono-((2R,3R,4S,5S,6R)-3,4,5-tris-benzoyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl) ester 
• 904691-44-7 phenyl (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside 
• 1381857-96-0 phenyl (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside 
• 1439439-53-8 phenyl 3,4-di-O-benzyl-2,6-di-O-levulinoyl-α-D-mannopyranosyl-(1→6)-2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside 
• 150935-68-5 phenyl 2,3,4-tri-O-benzoyl-1-thio-6-O-<2,3,4-tri-O-benzoyl-6-O-bis-(2,2,2-trichloroethoxy)phosphoryl-α-D-mannopyranosyl>-α-D-mannopyranoside 
• 150935-69-6 C₅₈H₄₈BrCl₆O₁₉P 
• 150935-70-9 1,3,4,6-tetra-O-acetyl-2-O-<2,3,4-tri-O-benzoyl-6-O-bis-(2,2,2-trichloroethoxy)phosphoryl-α-D-mannopyranosyl>-β-D-mannopyranose 
• 150935-71-0 C₄₃H₄₂BrCl₆O₁₉P 
• 150935-67-4 C₃₁H₂₆BrCl₆O₁₁P 
• 173207-93-7 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-α-D-mannopyranosyl bromide 
• 188397-32-2 N^α-(fluoren-9-ylmethoxycarbonyl)-O-[3,4,6-tri-O-acetyl-2-O-(2,3,4-tri-O-benzoyl-α-D-mannopyranosyl)-α-D-mannopyranosyl]-L-threonine 
• 188397-29-7 1,3,4,6-tetra-O-acetyl-2-O-(2,3,4-tri-O-benzoyl-6-O-chloroacetyl-α-D-mannopyranosyl)-β-D-mannopyranose 
• 188397-30-0 C₄₁H₄₀BrClO₁₇ 
• 188397-28-6 2,3,4-tri-O-benzoyl-6-O-chloroacetyl-α-D-mannopyranosyl bromide 

Relevant articles and documents

Synthesis of an Exhaustive Library of Naturally Occurring Gal f-Man p and Gal p-Man p Disaccharides. Toward Fingerprinting According to Ring Size by Advanced Mass Spectrometry-Based IM-MS and IRMPD

Nature offers a huge diversity of glycosidic derivatives. Among numerous structural modulations, the nature of the ring size of hexosides may induce significant differences on both biological and physicochemical properties of the glycoconjugate of interest. On this assumption, we expect that small disaccharides bearing either a furanosyl entity or a pyranosyl residue would give a specific signature, even in the gas phase. On the basis of the scope of mass spectrometry, two analytical techniques to register those signatures were considered, i.e., the ion mobility (IM) and the infrared multiple photon dissociation (IRMPD), in order to build up cross-linked databases. d-Galactose occurs in natural products in both tautomeric forms and presents all possible regioisomers when linked to d-mannose. Consequently, the four reducing Galf-Manp disaccharides as well as the four Galp-Manp counterparts were first synthesized according to a highly convergent approach, and IM-MS and IRMPD-MS data were second collected. Both techniques used afforded signatures, specific to the nature of the connectivity between the two glycosyl entities.

Constrained glycopeptide ligands for MPRs. Limitations of unprotected phosphorylated building blocks

A new methodology for the synthesis of cyclic and phosphorylated glycopeptide templates was developed. First, fully protected building blocks containing mannose and mannose disaccharides with bis-trichloroethyl phosphate on Fmoc-Thr-OPfp were synthesized. These were used in solid-phase assembly through side chain anchoring of glycosylated hexa- and octa-peptides protected at the C-terminal carboxylate as the allyl ester. Selective allyl ester cleavage and head-to-tail cyclization under pseudodilution conditions gave a high yield of pure cyclic peptide templates. Unprotected phosphate in the building block was evaluated as an alternative to the problematic trichloroethyl group. It was found that one unprotected phosphate is readily incorporated, whereas the second unprotected phosphorylated building block react very slowly due to electrostatic repulsion in the solid-phase synthesis. For comparison with previous binding studies modified glycopeptide templates containing only phosphorylated mannose monosaccharides or templates modified in the peptide part were synthesized. All the structures were tested for their binding to the mannose 6-phosphate receptor, and it was found that although mannose disaccharides are required for optimal interaction, the detailed structure of the peptide template has a strong influence on binding to the receptor. The restricted conformations of the cyclic peptides decreased the binding considerably.

Synthesis of aliphatic O-dimannosyl amino acid building blocks for solid-phase assembly of glycopeptide libraries

The preparations of α(1,2)-, α(1,3)- and α(1,6)-linked mannose disaccharides is described.The protected α-D-Man(1-->3)-D-Man disaccharide was synthesized using the trichloroacetimidate method, while the Koenigs-Knorr procedure was employed in the preparation of the 1-->2- and 1-->6-linked disaccharides.Glycosylation of NΑ-Fmoc-Ser-OPfp , Nα-Fmoc-Thr-OPfp and Nα-Fmoc-Hyp-OPfp with the dimannosyl bromides afforded the activated building blocks, in moderate to high yield, for direct use in solid-phase synthesis of glycopeptide libraries.

Synthesis of Mannose 6-Phosphate-containing Disaccharide Threonine Building Blocks and their Use in Solid-phase Glycopeptide Synthesis

The preparation of 6'-O-phosphorylated α(1,2)- and α(1,6)-linked mannose disaccharides is described, starting from phenyl 2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside and using bis-(2,2,2-trichloroethyl)phosphorochloridate as phosphorylating reagent.The mannobiosides were converted into glycosyl donors and used in glycosylations of Nα-Fmoc-Thr-OPfp.The resulting glycosylated building blocks, 11 and 12, were used in solid-phase glycopeptide synthesis of O-mannosylated tripeptides.

A stereospecific approach towards the synthesis of 2-deoxy α- and β-glycosides based on a 1,2-ethyl (phenyl) thio group migration

Iodonium ion (NIS/TfOH)-assisted glycosylation of a sugar acceptor with properly protected ethyl (phenyl) 2-O-phenoxythiocarbonyl 1-thio-β-D-gluco- or 1-thio-α-D-mannopyranoside donors gives the respective 1,2-trans linked 2'-ethyl (phenyl) thio-2'-deoxy-α-D-manno- or β-D-glucopyranosides.