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
• Article Data: 5

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

• 188397-33-3 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 pentafluorophenyl ester 
• 188397-31-1 N^α-(fluoren-9-ylmethoxycarbonyl)-O-[3,4,6-tri-O-acetyl-2-O-(2,3,4-tri-O-benzoyl-6-O-chloroacetyl-α-D-mannopyranosyl)-α-D-mannopyranosyl]-L-threonine pentafluorophenyl ester 
• 183158-62-5 N^α-(fluoren-9-ylmethoxycarbonyl)-O-[3,4,6-tri-O-acetyl-2-O-(2,3,4-tri-O-benzoyl-6-O-phosphate-α-D-mannopyranosyl)-α-D-mannopyranosyl]-L-threonine pentafluorophenyl ester 
• 188397-28-6 2,3,4-tri-O-benzoyl-6-O-chloroacetyl-α-D-mannopyranosyl bromide 
• 188397-30-0 C₄₁H₄₀BrClO₁₇ 
• 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 
• 188397-32-2 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 
• 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 
• 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 

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.

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.

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.