29019-41-8

Basic information

• Product Name: p-Tolyl O-(2,3,4,6,-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside
• Synonyms: p-Tolyl O-(2,3,4,6,-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside
• CAS NO: 29019-41-8
• Molecular Weight: 742.752
• Mol File: 29019-41-8.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 738.4±60.0 °C(Predicted)
• Density: 1.35±0.1 g/cm3(Predicted)
• CAS DataBase Reference: p-Tolyl O-(2,3,4,6,-tetra-O-acetyl-β-D-galactopyranosyl)-(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-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside(29019-41-8)
• EPA Substance Registry System: p-Tolyl O-(2,3,4,6,-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside(29019-41-8)

Safety Data

• Hazardous Substances Data: 29019-41-8(Hazardous Substances Data)

Upstream product

• 10486-08-5 sodium p-thiocresolate 
• 3616-19-1 1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 
• 106-45-6 para-thiocresol 
• 3616-19-1 lactose octaacetate 
• 4753-07-5 2,3,6,2',3',4',6'-hepta-O-acetyl-lactosyl bromide 
• 20764-63-0 β-cellobioseoctaacetate 
• 14227-66-8 acetobromocellobiose 

Downstream Products

• 27891-72-1 C₁₉H₂₈O₁₀S 
• 27894-74-2 4-methylphenyl (β-D-galactopyranosyl)-(1->4)-1-thio-β-D-glucopyranoside 

Relevant articles and documents

Concise Synthesis of 1-Thioalkyl Glycoside Donors by Reaction of Per-O-acetylated Sugars with Sodium Alkanethiolates under Solvent-Free Conditions

A relatively green method for synthesizing 1-thioalkyl glycosides has been developed, where sodium alkanethiolates were used to react with per-O-acetylated sugars instead of odorous alkyl mercaptans in the presence of BF3·Et2O without the use of solvents under mild conditions. Furthermore, we found that 1,2-trans-β-thioglycosides can be converted into corresponding 1,2-cis-α-thioglycosides in the presence of trifluoromethanesulfonic acid in nonpolar solvents under mild conditions. This provides a simple and efficient new approach for synthesizing challenging 1,2-cis-α-thioglycosides.

Reengineering Chemical Glycosylation: Direct, Metal-Free Anomeric O-Arylation of Unactivated Carbohydrates

To sustain innovation in glycobiology, effective routes to well-defined carbohydrate probes must be developed. For over a century, glycosylation has been dominated by the formation of the anomeric Csp3?O acetal junction in glycostructures. A dissociative mechanistic spectrum spanning SN1 and SN2 is frequently operational thereby reducing the efficiency. By reengineering this fundamental process, an orthogonal disconnection allows the acetal to be formed directly from the reducing sugar without the need for substrate pre-functionalisation. The use of stable aryliodonium salts facilitates a formal O?H functionalisation reaction. This allows lactols to undergo mild, metal-free O-arylation at ambient temperature. The efficiency of the transformation has been validated using a variety of pyranoside and furanoside monosaccharides in addition to biologically relevant di- and trisaccharides (up to 85 %). Fluorinated mechanistic probes that augment the anomeric effect were employed. It is envisaged that this strategy will prove expansive for the construction of complex acetals under substrate-based stereocontrol.

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.