70751-54-1

Basic information

• Product Name: 1,2:3:4-di-O-isopropylidene-6-O-(tetra-O-benzoyl-β-D-glucopyranosyl)-α-D-galactose
• Synonyms: 1,2:3:4-di-O-isopropylidene-6-O-(tetra-O-benzoyl-β-D-glucopyranosyl)-α-D-galactose
• CAS NO: 70751-54-1
• Molecular Weight: 838.862
• Mol File: 70751-54-1.mol
• Article Data: 45

Chemical Properties

• CAS DataBase Reference: 1,2:3:4-di-O-isopropylidene-6-O-(tetra-O-benzoyl-β-D-glucopyranosyl)-α-D-galactose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2:3:4-di-O-isopropylidene-6-O-(tetra-O-benzoyl-β-D-glucopyranosyl)-α-D-galactose(70751-54-1)
• EPA Substance Registry System: 1,2:3:4-di-O-isopropylidene-6-O-(tetra-O-benzoyl-β-D-glucopyranosyl)-α-D-galactose(70751-54-1)

Safety Data

• Hazardous Substances Data: 70751-54-1(Hazardous Substances Data)

Upstream product

• 157896-05-4 Phenyl 2,3,4,6-tetra-O-benzoyl-1-seleno-β-D-glucopyranoside 
• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 183367-62-6 1-phenyltelluro-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside 
• 920749-30-0 C₃₉H₃₄O₁₁ 
• 953795-81-8 C₃₇H₃₀O₁₀ 
• 247257-17-6 (2R,3R,4S,5R,6S)-2-((benzoyloxy)methyl)-6-mercaptotetrahydro-2H-pyran-3,4,5-triyl tribenzoate 
• 212128-04-6 4-acetamidophenyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-galactopyranoside 
• 62774-33-8 phenyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-galactopyranoside 
• 953795-90-9 C₃₇H₃₀O₁₀ 
• 744245-92-9 2-thiazolinyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside 
• 635727-37-6 2-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosylmercapto)-1,3-benzoxazole 
• 339276-12-9 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate 
• 869384-37-2 1-deoxy-1-[(R/S)-(phenyl)sulfinyl]-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranose 
• 62774-33-8 phenyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside 

Relevant articles and documents

Triflic Imide-Catalyzed Glycosylation of Disarmed Glycosyl ortho-Isopropenylphenylacetates and ortho-Isopropenylbenzyl Thioglycosides

Glycosylation reaction involving the coupling of a glycosyl donor with a glycosyl acceptor is one of the cornerstones of chemical preparation of pure glycans and glycoconjugates of biological relevance. Catalytic glycosylation of glycosyl ester donors and thioglycosides is an attractive but underexplored topic in carbohydrate chemistry. Herein, triflic imide (Tf2NH)-catalyzed glycosylation of various O-, S-, and C-nucleophiles has been achieved using disarmed glycosyl ortho-isopropenylphenylacetates (GIPPAs) and ortho-isopropenylbenzyl thioglycosides as glycosylating agents. The reactions proceed under mild conditions to give the desired glycosides in good-to-excellent yields. Of particular note, the comparable reactivity for the α-isomers and the β-ones of GIPPAs is observed. The mechanistic investigation demonstrates that the isopropenyl group is essential for the reaction and its preferential protonation triggers the reaction. This work provides another member to the arsenals of glycosyl ester and thioglycoside donors suitable for acid-catalyzed glycosylation to create various glycosidic bonds.

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.

A Mild Glycosylation Protocol with Glycosyl 1-Methylimidazole-2-carboxylates as Donors

A mild glycosylation protocol is developed by using glycosyl 1-methylimidazole-2-carboxylates. Such a glycosylation can be promoted by a series of metal triflates and triflimides, especially Cu(OTf)2. The reaction is initiated by activation of