118545-28-1

Basic information

• Product Name: methyl (2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside
• Synonyms: methyl (2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside
• CAS NO: 118545-28-1
• Molecular Weight: 950.993
• Mol File: 118545-28-1.mol
• Article Data: 15

Chemical Properties

• CAS DataBase Reference: methyl (2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside(118545-28-1)
• EPA Substance Registry System: methyl (2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside(118545-28-1)

Safety Data

• Hazardous Substances Data: 118545-28-1(Hazardous Substances Data)

Upstream product

• 14218-11-2 2,3,4,6-tetra-O-benzoylglucosyl bromide 
• 76375-66-1 methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 744245-92-9 2-thiazolinyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside 
• 62774-33-8 phenyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-galactopyranoside 
• 1221151-98-9 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl ortho-(hex-1-ynyl)benzoate 
• 91958-78-0 2-(β-D-glucopyranosylmercapto)-1,3-benzoxazole 
• 6044-27-5 benzoxazol-2-yl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 635727-37-6 2-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosylmercapto)-1,3-benzoxazole 
• 149707-75-5 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate 
• 104707-00-8 methyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside 

Downstream Products

• 203717-62-8 C₅₅H₅₂O₁₅ 

Relevant articles and documents

NIS/TMSOTf-Promoted Glycosidation of Glycosyl ortho-Hexynylbenzoates for Versatile Synthesis of O-Glycosides and Nucleosides

Glycosidation plays a pivotal role in the synthesis of O-glycosides and nucleosides that mediate a diverse range of biological processes. However, efficient glycosidation approach for the synthesis of both O-glycosides and nucleosides remains challenging in terms of glycosidation yields, mild reaction conditions, readily available glycosyl donors, and cheap promoters. Here, we report a versatile N-iodosuccinimide/trimethylsilyl triflate (NIS/TMSOTf)-promoted glycosidation approach with glycosyl ortho-hexynylbenzoates as donors for the highly efficient synthesis of O-glycosides and nucleosides. The glycosidation approach highlights the merits of mild reaction conditions, cheap promoters, extremely wide substrate scope, and good to excellent yields. Notably, the glycosidation approach performs very well in the construction of a series of challenging O- and N-glycosidic linkages. The glycosidation approach is then applied to the efficient synthesis of oligosaccharides via the one-pot strategy and the stepwise strategy. On the basis of the isolation and characterization of the departure species derived from the leaving group, a plausible mechanism of NIS/TMSOTf-promoted glycosidation of glycosyl ortho-hexynylbenzoates is proposed.

Ortho-(1-phenylvinyl)benzoate glycosylation donor, and preparation method and application thereof

The invention discloses an ortho-(1-phenylvinyl)benzoate glycosylation donor, and a preparation method and an application thereof in a glycosylation reaction. The ortho-(1-phenylvinyl)benzoate glycosylation donor is stable, is easy to prepare and store, and is widely applied to the construction of various oxygen glucosides and nucleoside (nitrogen glucoside) glycosidic bonds. The leaving group ofthe donor is an alkenyl ester, has a high activity, and can be combined with thioglycoside or n-pentenyl ether glucoside through a one-pot glycosylation reaction to synthesize oligosaccharide. The glycosylation reaction conditions are mild, and receptors sensitive to acid and electrophilic reagents can tolerate the glycosylation reaction conditions.

O,O-Dimethylthiophosphonosulfenyl bromide-silver triflate: A new powerful promoter system for the preactivation of thioglycosides

O,O-Dimethylthiophosphonosulfenyl bromide (DMTPSB) in combination with silver triflate provides a powerful thiophilic promoter system. Both "armed" and "disarmed" thioglycoside glycosyl donors can be activated to form glycosidic linkages efficiently by th