154703-95-4

Upstream product

• 19488-48-3 methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 4098-06-0 triacetyl-D-galactal 
• 154801-52-2 3-β-pyridylthio-4,6-O-diacetyl-2,3-dideoxy-D-galactal 
• 154703-87-4 Acetic acid (2R,3R,6R)-2-acetoxymethyl-6-(pyridin-2-ylsulfanyl)-3,6-dihydro-2H-pyran-3-yl ester 
• 125848-19-3 phenyl-2,4-di-O-acetyl-2,3-dideoxy-1-thio-α-D-threo-hex-2-eno-pyranoside 

Downstream Products

• 177263-34-2 (2R,3R,6R)-6-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-hydroxymethyl-3,6-dihydro-2H-pyran-3-ol 
• 177263-35-3 (2R,3R,6R)-6-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-ol 
• 177263-36-4 2,2,2-Trichloro-acetimidic acid (2R,3R,6R)-6-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-yl ester 
• 177263-33-1 N-[(2R,3S,6S)-2-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-yl]-2,2,2-trichloro-acetamide 
• 177263-37-5 N-[(1R,2R,4R,5S,6R)-4-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,7-dioxa-bicyclo[4.1.0]hept-5-yl]-2,2,2-trichloro-acetamide 
• 177263-41-1 N-[(2R,3S,4R,5R,6R)-2-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dihydroxy-tetrahydro-pyran-3-yl]-2,2,2-trichloro-acetamide 
• 177263-40-0 N-[(2R,3S,4S,5S,6R)-2-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dihydroxy-tetrahydro-pyran-3-yl]-2,2,2-trichloro-acetamide 

Relevant academic research and scientific papers

Palladium(II) promoted O-glycosylation involving 1-thio-2-enosides and 3-thio-1-enoses

O-glycosylation of thioglycosyl donors, 2,3-dideoxy-hex-l-thio-2-enopyranosides, 1,2-dideoxy-hex-3-thio-1-nopyranoses and 2-pyridyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside was achieved by use of a Pd(II) activator which was prepared from bis(acetonitrile)dichloropalladium(II)(Pd(CH3CN)2Cl 2) and silver triflate (AgOTf).

Copper(ii)-catalyzed stereoselective 1,2-addition: Vs. Ferrier glycosylation of "armed" and "disarmed" glycal donors

Selective activation of "armed' and "disarmed"glycal donors enabling the stereo-controlled glycosylations by employing Cu(ii)-catalyst as the promoter has been realized. The distinctive stereochemical outcome in the process is mainly influenced by the presence of diverse protecting groups on the donor and the solvent system employed. The protocol is compatible with a variety of aglycones including carbohydrates, amino acids, and natural products to access deoxy-glycosides and glycoconjugates with high α-anomeric selectivity. Notably, the synthetic practicality of the method is amply verified for the stereoselective assembling of trisaccharides comprising 2-deoxy components. Mechanistic studies involving deuterated experiments validate the syn-diastereoselective 1,2-addition of acceptors on the double bond of armed donors.

Scope of AuCl3 in the activation of per-O-acetylglycals

Gold(III)chloride in catalytic amounts activates 3,4,6-tri-O-acetyl-d-glucal, 3,4,6-tri-O-acetyl-d-galactal, and 3,4-di-O-acetyl-l-rhamnal efficiently. The activated species can be employed in the Ferrier reaction with different nucleophiles at ambient conditions. Attempts have been made to make β-anomer of the Ferrier product from anomeric-O-propargylated Ferrier product.

Niobium(V) chloride catalyzed microwave assisted synthesis of 2,3-unsaturated O-glycosides by the Ferrier reaction

NbCl5 catalyzes the Ferrier reaction of per-O-acetylated glycals with primary, secondary, allylic, benzylic and monosaccharide alcohols to give 2,3-unsaturated α-glycosides in short reaction times under microwave irradiation conditions.

Synthesis of 2-amino-2-deoxy-D-hexopyranoside-containing disaccharides involving glycosylation and [3,3] sigmatropic rearrangement

The syntheses of D-mannosamine 15, D-idosamine 16, D-altrosamine 19, and D-tallosamine 20 derivatives of 2-amino-2-deoxy-D-hexopyranoside-containing disaccharides were achieved by [3,3] sigmatropic rearrangement reaction of the disaccharide 13 having a 4-trichloroacetimidate-2-enoside group, prepared in turn by glycosylation of thioglycosyl donors using Pd(CH3CN)2Cl2-AgOTf as a promoter.