755002-33-6

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 457931-46-3 4-methylphenyl 1-thio-α-D-mannopyranoside 
• 211801-79-5 4-methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 
• 942043-27-8 4-methylphenyl 2,3,4,6-tetra-O-trimethylsilyl-1-thio-α-D-mannopyranoside 
• 100-52-7 benzaldehyde 
• 106-45-6 para-thiocresol 
• 83-87-4 D-Mannose pentaacetate 

Downstream Products

• 1320281-31-9 p-tolyl 4,6-di-O-acetyl-2,3-di-O-benzyl-1-thio-α-D-mannopyranoside 
• 1320281-32-0 methyl (p-tolyl 4-O-acetyl-2,3-di-O-benzyl-1-thio-α-D-mannopyranosyl uronate) 
• 1157902-57-2 4-methylphenyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 
• 1428876-61-2 4-methylphenyl 3-O-acetyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 
• 1428876-62-3 4-methylphenyl 2,3-di-O-acetyl-4-O-benzyl-1-thio-α-D-mannopyranoside 
• 950602-62-7 p-methylphenyl 2-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 
• 1425378-08-0 C₅₉H₆₁NO₁₀ 
• 1407967-81-0 (4-methylphenyl) 2-O-benzyl-4,6-O-benzylidene-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside 
• 1407152-00-4 C₃₄H₃₂O₆S 

Relevant academic research and scientific papers

Acceptor Reactivity in the Total Synthesis of Alginate Fragments Containing α- L -Guluronic Acid and β- D -Mannuronic Acid

The total synthesis of mixed-sequence alginate oligosaccharides, featuring both β-D-mannuronic acid (M) and α-L-guluronic acid (G), is reported for the first time. A set of GM, GMG, GMGM, GMGMG, GMGMGM, GMGMGMG, and GMGGMG alginates was assembled using GM

Regioselective and stereoselective benzylidene installation and one-pot protection of d-mannose

Oligosaccharide syntheses are an important source of well-defined sugar constructs particularly needed for the evaluation of structure-activity relationships. The chemical assembly of oligosaccharides requires several building blocks, that is, glycosyl donors and acceptors, which are prepared in multistep processes and in a generally tedious and time-consuming manner. Having developed one-pot procedures meant to minimise the effort in sugar building block preparation, we tackled herein the one-pot preparation of fully protected and 2-, 3-, 4-, and 6-alcohol derivatives of d-mannose, a widely distributed monosaccharide. As a consequence of the hydroxyl group pattern of d-mannose, regioselective and stereoselective benzylidenations were developed and later seamlessly utilised as the first transformation in the one-pot procedure.

In situ formation of β-glycosyl imidinium triflate from participating thioglycosyl donors: Elaboration to disarmed-armed iterative glycosylation

β-Glycosyl imidinium triflate is generated from participating thioglycoside donors for disarmed-armed iterative glycosylations and one-pot oligosaccharide synthesis.

Mannopyranosyl uronicaAcid donor reactivity

The reactivity of a variety of mannopyranosyl uronic acid donors was assessed in a set of competition experiments, in which two (S)-tolyl mannosyl donors were made to compete for a limited amount of promoter (NIS/TfOH). These experiments revealed that the reactivity of mannuronic acid donors is significantly higher than expected based on the electron-withdrawing capacity of the C-5 carboxylic acid ester function. A 4-O-acetyl-β-(S)-tolyl mannuronic acid donor was found to have similar reactivity as per-O-benzyl-α-(S)-tolyl mannose.

Efficient formation and cleavage of benzylidene acetals by sodium hydrogen sulfate supported on silica gel

NaHSO4SiO2 was used as an efficient heterogeneous catalyst for both the formation and the cleavage of benzylidene acetals. This catalyst is compatible with many functional or protective groups. Under different solvent systems, either the formation or the cleavage of benzylidene acetals was carried out smoothly in excellent yields and with good chemoselectivity. Georg Thieme Verlag Stuttgart.

4,6-O-benzylidene directed β-mannosylation without intermediate triflate formation? Comparison of trichloroacetimidate and disal donors in microwave-promoted glycosylations under neutral conditions

4,6-Benzylidene-protected mannosyl donors have emerged as efficient tools for the formation of 1,2-cis β-mannosides, which otherwise are difficult to access. Previously studied sulfoxide and trichloroacetimidate mannosyl donors were activated with strong

Allyl protecting group mediated intramolecular aglycon delivery: Optimisation of mixed acetal formation and mechanistic investigation

An efficient protocol for the formation of α-iodo mixed acetals, the first step of allyl-mediated IAD, by reaction of allyl-derived enol ethers and alcohols, using I2, AgOTf and di-tert-butyl methylpyridine as a novel source of I+, i