27894-92-4

Basic information

• Product Name: p-tolyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside
• Synonyms: p-tolyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside
• CAS NO: 27894-92-4
• Molecular Weight: 742.752
• Mol File: 27894-92-4.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: p-tolyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: p-tolyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside(27894-92-4)
• EPA Substance Registry System: p-tolyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside(27894-92-4)

Safety Data

• Hazardous Substances Data: 27894-92-4(Hazardous Substances Data)

Upstream product

• 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 
• 106-45-6 para-thiocresol 
• 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 
• 14227-66-8 acetobromocellobiose 

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 articles and documents

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.

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.

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.