211801-79-5

Basic information

• Product Name: 4-methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside
• Synonyms: 4-methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside
• CAS NO: 211801-79-5
• Molecular Weight: 454.498
• Mol File: 211801-79-5.mol
• Article Data: 24

Chemical Properties

• CAS DataBase Reference: 4-methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside(211801-79-5)
• EPA Substance Registry System: 4-methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside(211801-79-5)

Safety Data

• Hazardous Substances Data: 211801-79-5(Hazardous Substances Data)

Upstream product

• 103-19-5 di(p-tolyl) disulfide 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 530-26-7 D-Mannose 
• 108-24-7 acetic anhydride 
• 106-45-6 para-thiocresol 
• 83-87-4 D-Mannose pentaacetate 

Downstream Products

• 1263417-47-5 methyl 3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 130144-06-8 methyl 2-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)(1→3)-4,6-O-benzylidene-α-D-glucopyranoside 
• 55094-26-3 methyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)-α-D-glucopyranoside 
• 55094-26-3 methyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 3879-79-6 (2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran 
• 71526-33-5 methyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranoside 

Relevant articles and documents

Developing a library of mannose-based mono-and disaccharides: A general chemoenzymatic approach to monohydroxylated building blocks

Regioselective deprotection of acetylated mannose-based mono-and disaccharides differently functionalized in anomeric position was achieved by enzymatic hydrolysis. Candida rugosa lipase (CRL) and Bacillus pumilus acetyl xylan esterase (AXE) were immobilized on octyl-Sepharose and glyoxyl-agarose, respectively. The regioselectivity of the biocatalysts was affected by the sugar structure and functionalization in anomeric position. Generally, CRL was able to catalyze regioselective deprotection of acetylated monosaccharides in C6 position. When acetylated disaccharides were used as substrates, AXE exhibited a marked preference for the C2, or C6 position when C2 was involved in the glycosidic bond. By selecting the best enzyme for each substrate in terms of activity and regioselectivity, we prepared a small library of differently monohydroxylated building blocks that could be used as intermediates for the synthesis of mannosylated glycoconjugate vaccines targeting mannose receptors of antigen presenting cells.

Synthesis of disaccharide modified berberine derivatives and their anti-diabetic investigation in zebrafish using a fluorescence-based technology

Berberine is a naturally occurring isoquinoline alkaloid and has been used as an important functional food additive in China due to its various pharmacological activities. Berberine exhibits great potential for developing anti-diabetic agents against type

Triflic acid-mediated synthesis of thioglycosides

An efficient synthesis of thioglycosides from per-acetates in the presence of triflic acid is described. The developed protocol features high reaction rates and product yields. Some reactive sugar series give high efficiency in the presence of sub-stoichiometric trifluoromethanesulfonic acid (TfOH) in contrast to other known protocols that require multiple equivalents of Lewis acids to reach high conversion rates.