398488-13-6

Upstream product

• 108-98-5 thiophenol 
• 39686-94-7 1,2,4,6-tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose 
• 189144-54-5 phenyl 3-O-benzyl-1-thio-β-D-glucopyranoside 
• 460082-41-1 phenyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 225241-34-9 phenyl 4,6-O-p-methoxybenzylidene-1-thio-β-D-glucopyranoside 
• 158198-55-1 phenyl 2,4,6-tri-O-acetyl-3-O-benzyl-1-thio-β-D-glucopyranoside 

Downstream Products

• 1415996-70-1 C₅₁H₄₉N₃O₁₁S 
• 1415996-29-0 C₅₁H₅₁NO₁₁S 
• 1415995-97-9 C₅₄H₅₂Cl₃NO₁₃S 
• 1415996-32-5 C₅₆H₅₃Cl₄NO₁₄S 
• 850637-47-7 (2S,3S,4S,5R,6S)-3-((2R,3R,4R,5S,6R)-6-Acetoxymethyl-3-azido-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-5-benzoyloxy-4-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 850637-29-5 methyl (phenyl 2-O-benzoyl-3-O-benzyl-1-thio-β-D-glucopyranosyluronate) 
• 850637-28-4 phenyl 2-O-benzoyl-3-O-benzyl-1-thio-β-D-glucopyranosyluronic acid 

Relevant academic research and scientific papers

Synthesis and reactivity of 4'-deoxypentenosyl disaccharides

4-Deoxypentenosides (4-DPs) are versatile synthons for rare or higher-order pyranosides, and they provide an entry for structural diversification at the C5 position. Previous studies have shown that 4-DPs undergo stereocontrolled DMDO oxidation; subsequent epoxide ring-openings with various nucleophiles can proceed with both anti or syn selectivity. Here, we report the synthesis of α- and β-linked 4'-deoxypentenosyl (4'-DP) disaccharides, and we investigate their post-glycosylational C5' additions using the DMDO oxidation/ring-opening sequence. The α-linked 4'-DP disaccharides were synthesized by coupling thiophenyl 4-DP donors with glycosyl acceptors using BSP/Tf2O activation, whereas β-linked 4'-DP disaccharides were generated by the decarboxylative elimination of glucuronyl disaccharides under microwave conditions. Both α- and β-linked 4'-DP disaccharides could be epoxidized with high stereoselectivity using DMDO. In some cases, the α-epoxypentenosides could be successfully converted into terminal l-iduronic acids via the syn addition of 2-furylzinc bromide. These studies support a novel approach to oligosaccharide synthesis, in which the stereochemical configuration of the terminal 4'-DP unit is established at a post-glycosylative stage.

Convergent stereoselective synthesis of multiple sulfated GlcNα(1,4)GlcAβ(1,4) dodecasaccharides

In this paper, we describe an effective method for the elongation of a GlcNα(1,4)GlcAβ(1,4) sequence using a GlcNTrocα(1,4)GlcA disaccharide unit and the synthesis of the N- and/or O-sulfated GlcNα(1,4)GlcAβ(1,4) oligosaccharides. N-Troc protection of Glc

A modular strategy toward the synthesis of heparin-like oligosaccharides using monomeric building blocks in a sequential glycosylation strategy

A novel flexible assembly strategy is described for the modular synthesis of heparin and heparan sulfates. The reported strategy uses monomeric building bocks to construct the oligosaccharide chain to attain a maximum degree of flexibility. In the assembly, 1-hydroxyl glucosazido- and 1-thio uronic acid donors are combined in a sequential glycosylation protocol using sulfonium triflate activator systems. The key 1-thio uronic acids were obtained in an efficient manner from diacetone glucose employing a chemo- and regioselective oxidation of partially protected glucose and idose thioglycosides.