27894-92-4

Upstream product

• 106-45-6 para-thiocresol 
• 14227-66-8 acetobromocellobiose 
• 98-59-9 p-toluenesulfonyl chloride 
• 4753-07-5 2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-maltosyl bromide 
• 3616-19-1 1,2,3,6,2',3',4',6'-octa-O-acetylmaltose 
• 22352-19-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl acetate 
• 20764-63-0 β-cellobioseoctaacetate 

Downstream Products

• 27891-72-1 C₁₉H₂₈O₁₀S 
• 1582735-40-7 C₄₁H₄₆O₁₄S 
• 1582735-37-2 C₃₄H₄₀O₁₄S 
• 1582735-38-3 C₄₁H₄₆O₁₆S₂ 
• 1582735-36-1 C₃₃H₃₈O₁₂S₂ 
• 1582735-35-0 C₂₆H₃₂O₁₀S 
• 27891-75-4 C₁₉H₂₈O₁₀S 
• 1582735-54-3 C₄₅H₅₂Cl₃NO₁₅Si 
• 1582735-52-1 C₅₀H₅₈O₁₄SSi 
• 1582735-43-0 C₄₂H₅₀O₁₀SSi 
• 1582735-42-9 C₃₃H₃₆O₁₁S 

Relevant academic research and scientific papers

Boron-Promoted Umpolung Reaction of Sulfonyl Chlorides for the Stereospecific Synthesis of Thioglycosides via Reductive Deoxygenation Coupling Reactions

S-Glycosides have broad biological activities and serve as stable mimics of natural O-glycoside counterparts and thus are of great therapeutic potential. Herein we disclose an efficient method for the stereospecific synthesis of 1-thioglycosides via a boron-promoted reductive deoxygenation coupling reaction from readily accessible sulfonyl chlorides and glycosyl bromides. Our protocol features mild conditions and excellent functional group tolerance and stereoselectivity. The translational potential of this metal-free approach is demonstrated by the late-stage glycodiversification of natural products and drug molecules.

Synthesis of three OSW-1 analogs with maltose side chains bearing different protection groups

In order to simplify the synthesis of OSW-1's disaccharide side chain and explore the structure-activity relationship of OSW-1, three 16α-O-maltose OSW-1 analogs carrying three maltose side chains bearing different protections were designed and synthesized.

A facile and efficient method for the one-pot synthesis of per-O-acetylated thioglycosides from unprotected sugars

An efficient, convenient protocol for the preparation of per-O-acetylated p-tolylthio glycosides is described. Treatment of various unprotected sugars, including 2-deoxy-2-amino sugars, sialic acid, lactose, and maltose, with acetic anhydride using SnCl4 as a catalyst, and subsequently with p-tolylthiol, furnished the corresponding thioglycosides in 71%-90% yield under solvent-free conditions.

Chemoselective deacylation of functionalized esters catalyzed by dioxomolybdenum dichloride

Among five different oxidometallic species and two Lewis acids investigated, MoO2Cl2 shows the best catalytic and chemoselective activity for the deacylation of esters in methanol at ambient or elevated temperature. Both high efficiency and chemoselectivity were achieved for substrates bearing different ether or ester groups. Acylated mono and disaccharides can also be selectively deacetylated in good yields, leading to useful carbohydrate templates for further synthetic manipulations.

Lanthanum trifluoromethane-sulfonate-catalyzed facile synthesis of per-O-acetylated sugars and their one-pot conversion to S-aryl and O-alkyl/aryl glycosides

Lanthanum trifluoromethanesulfonate-catalyzed solvent-free per-O-acetylation with stoichiometric acetic anhydride proceeds in high yield (95%-99%) to afford exclusively pyranose products as anomeric mixtures. Subsequent anomeric substitution employing borontrifluoride etherate and thiols or alcohols furnished the corresponding 1,2-trans-linked thioglycosides and O-glycosides, respectively, in good to excellent overall yield (75%-85%). Alternatively, reaction of free sugars in neat alcohol employing the same catalyst at elevated temperature gives the corresponding 1,2-cis-linked O-glycosides (along with 1,2-trans-linked glycosides as minor product) in good yield (73%-80%). Anomeric mixtures of compounds thus produced were characterized as their per-O-acetylated derivatives.

Large-scale synthesis of per-O-acetylated saccharides and their sequential transformation to glycosyl bromides and thioglycosides

This work describes a large-scale synthesis of per- O -acetylated mono- and disaccharides using a stoichiometric amount of acetic anhydride in the presence of LiClO 4 under solvent-free conditions. The peracetylated saccharides underwent subsequent anomeric bromination and thioglycosidation in one-pot to yield synthetically valuable building blocks. Copyright Taylor & Francis Group, LLC.

Stereoselective syntheses of 1,2-trans p-MePh and 2-pyridyl 1- thioglycosides catalyzed by zirconium(IV) chloride

1-Thioglycosides including per-O-acetyl p-MePh and 2-pyridyl 1- thioglycosides were chemically synthesized with high complete stereoselectivity by using ZrCl4 as catalyst.