154172-24-4

Upstream product

• 119237-86-4 allyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside 
• 7296-15-3 alpha-D-mannopyranoside 
• 530-26-7 D-Mannose 
• 83-87-4 D-Mannose pentaacetate 
• 159407-17-7 phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 
• 159407-19-9 phenyl 4,6-O-benzylidene-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 
• 3458-28-4 D-Mannose 
• 41308-76-3 allyl α-D-mannopyranoside 
• 81600-93-3 allyl 4,6-di-O-benzylidene-α-D-mannopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 

Downstream Products

• 556062-74-9 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl diphenyl phosphate 
• 920976-12-1 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl pent-4-enoate 
• 722504-13-4 (2R,4R,5R)-4-((1R,2R)-1,2-Bis-benzyloxy-3-hydroxy-propyl)-2-phenyl-[1,3]dioxan-5-ol 
• 721448-02-8 N-{(2R,4R,5R)-4-[(1S,2R)-1,2-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-propyl]-2-phenyl-[1,3]dioxan-5-yl}-acetamide 
• 721448-06-2 N-[(2R,4R,5R)-2-Phenyl-4-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-[1,3]dioxan-5-yl]-acetamide 
• 721448-04-0 N-[(2R,4R,5R)-4-((1S,2R)-1,2-Bis-benzyloxy-3-hydroxy-propyl)-2-phenyl-[1,3]dioxan-5-yl]-acetamide 
• 721448-08-4 N-((1R,2R,3S,4R)-3,4,5-Tris-benzyloxy-2-hydroxy-1-hydroxymethyl-pentyl)-acetamide 
• 1037510-13-6 (2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1->4)-1-O-methyl-2,3,6-tri-O-benzyl-α-D-glucopyranose 

Relevant academic research and scientific papers

Electrochemical Synthesis of Glycosyl Fluorides Using Sulfur(VI) Hexafluoride as the Fluorinating Agent

This manuscript describes the electrochemical synthesis of 17 different glycosyl fluorides in 73-98% yields on up to a 5 g scale that relies on the use of SF6 as an inexpensive and safe fluorinating agent. Cyclic voltammetry and related mechanistic studies carried out subsequently suggest that the active fluorinating species generated through the cathodic reduction of SF6 are transient under these reductive conditions and that the sulfur and fluoride byproducts are effectively scavenged by Zn(II) to generate benign salts.

Synthesis of Glycosyl Fluorides by Photochemical Fluorination with Sulfur(VI) Hexafluoride

This study describes a new convenient method for the photocatalytic generation of glycosyl fluorides using sulfur(VI) hexafluoride as an inexpensive and safe fluorinating agent and 4,4′-dimethoxybenzophenone as a readily available organic photocatalyst. This mild method was employed to generate 16 different glycosyl fluorides, including the substrates with acid and base labile functionalities, in yields of 43%-97%, and it was applied in continuous flow to accomplish fluorination on an 7.7 g scale and 93% yield.

Influence of protecting groups on the anomeric equilibrium; Case of the 4,6-O-benzylidene acetal in the mannopyranose series

It is reported that the replacement of the 4- and 6-O-benzyl ethers in 2,3,4,6-tetra-O-benzyl-α,β-mannopyranose by a 4,6-O-benzylidene acetal results in an increased population of the β-anomer at equilibrium in CDCl3 solution. The phenomenon is considered to arise from the lower steric bulk of the benzylidene acetal that, through diminished buttressing interactions, reduces steric interactions normally present in the β-anomer.

Synthesis of |β-(1→2)-linked oligomannosides

β-(1→2)-Linked oligomannosides constitute an important class of carbohydrate structures located on the cell surface of several Candida species, including C. albicans. As a result of the immunostimulating properties of such compounds, the upscaling of their synthesis is relevant. In this paper, a highly stereoselective synthesis of |β-(1→2)-linked oligomannosides was performed by further development of and modifications to the methodologies described earlier in the literature. In addition to the synthesis of fully deprotected β-(1→2)-linked mannobiose and mannotriose, some preliminary modifications to the oligosaccharide core, resulting in close analogues with biological potential, are presented. The fully deprotected products form potential targets for screening against C. albicans and may also result in new model structures for vaccine development.

Efficient installation of β-mannosides using a dehydrative coupling strategy

(Chemical Equation Presented) A new coupling procedure for the construction of the challenging β-mannosidic bond is described. Dehydrative mannosylation using 4,6-O-benzylidene mannopyranoses allows for the formation of β-mannosides in excellent yield. Th

Synthesis of a novel dioxan sialic acid analog

A preparative scale synthesis of a dioxan sialic acid analog was achieved from D-mannose. The conformation and the acidic character of this dioxan derivative, closely related to sialic acid, provides a scaffold for drug design.