159407-19-9

Usage

Uses

Used in Organic Synthesis:
Phenyl 4,6-O-Benzylidene-1-thio-α-D-mannopyranoside is used as a synthetic building block for the creation of complex organic molecules. Its unique structure allows for a wide range of applications in the synthesis of various compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Phenyl 4,6-O-Benzylidene-1-thio-α-D-mannopyranoside is used as a key intermediate in the synthesis of novel drug candidates. Its unique structure can be exploited to design and develop new molecules with potential therapeutic applications.
Used in Research and Development:
Phenyl 4,6-O-Benzylidene-1-thio-α-D-mannopyranoside is also used in research and development laboratories for the study of various chemical reactions and processes. Its unique structure makes it an ideal candidate for exploring new synthetic routes and methodologies in organic chemistry.
Used in Material Science:
In the field of material science, Phenyl 4,6-O-Benzylidene-1-thio-α-D-mannopyranoside can be used as a component in the development of new materials with specific properties. Its unique structure can contribute to the design of materials with tailored characteristics, such as improved stability, reactivity, or selectivity.

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 2936-70-1 (2R,3S,4S,5S,6R)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 
• 13992-16-0 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 
• 530-26-7 D-Mannose 
• 108-98-5 thiophenol 
• 83-87-4 D-Mannose pentaacetate 
• 65236-83-1 phenyl 2,3,4,6-tetra-O-benzoyl-1-thio-α-D-mannopyranoside 
• 151763-69-8 phenyl 1-thio-D-mannopyranoside 
• 121524-01-4 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-mannopyranoside 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 

Downstream Products

• 158716-07-5 phenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 
• 168138-26-9 phenyl 4,6-O-benzylidene-3-O-(4-methoxybenzyl)-1-thio-α-D-mannopyranoside 
• 407616-82-4 S-phenyl 2,3-di-O-allyl-4,6-O-benzylidene-1-thia-α-D-mannopyranoside 
• 634597-88-9 (2R,4aR,6R,7S,8R,8aR)-8-(tert-Butyl-diphenyl-silanyloxy)-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 
• 915221-33-9 phenyl 4,6-O-benzylidene-3-O-(3-naphthalen-1-yl-prop-2-ynyl)-1-thio-α-D-mannopyranoside 
• 855306-46-6 methyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-β-D-mannopyranoside 
• 855306-33-1 phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-1-thio-α-D-mannopyranoside 
• 951025-10-8 phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-β-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-2-O-(prop-2-ynyl)-1-thio-α-D-mannopyranoside 
• 951025-13-1 methyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-(2-naphthylmethyl)-β-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-2-O-(prop-2-ynyl)-β-D-mannopyranosyl-(1->3)-4,6-benzylidene-2-O-(prop-2-ynyl)-β-D-mannopyranoside 
• 951025-07-3 phenyl 4,6-O-benzylidene-3-O-(2-naphthylmethyl)-2-O-(prop-2-ynyl)-1-thio-α-D-mannopyranoside 
• 951025-08-4 methyl 4,6-O-benzylidene-3-O-(2-naphthylmethyl)-2-O-(prop-2-ynyl)-β-D-mannopyranoside 
• 951025-09-5 phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-(2-naphthylmethyl)-β-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-2-O-(prop-2-ynyl)-1-thio-α-D-mannopyranoside 
• 915221-35-1 phenyl 4,6-O-benzylidene-2-O-(3-naphthalen-1-yl-prop-2-ynyl)-3-O-benzyl-1-thio-α-D-mannopyranoside 

Relevant academic research and scientific papers

Synthesis of optically pure, differentially protected 1,4- and 1,6-mannosyl-D-myo-inositol derivatives from 7-oxabicyclo[2.2.1]heptan-2-one

Efficient procedures to prepare 4-O-mannosyl conduritol B derivatives from mannosyl oxanorbornanes are described. The osmium-catalyzed cis-dihydroxylation of the corresponding 1-O-acetates displays high π-facial selectivity syn to the acetate functionalit

Stereoselective O-Glycosylations by Pyrylium Salt Organocatalysis**

Despite many years of invention, the field of carbohydrate chemistry remains rather inaccessible to non-specialists, which limits the scientific impact and reach of the discoveries made in the field. Aiming to increase the availability of stereoselective

Deuterium labelling to extract local stereochemical information by VCD spectroscopy in the C-D stretching region: A case study of sugars

Stereochemical elucidation of molecules with multiple chiral centers is difficult. Even with VCD spectroscopy, excluding all but one diastereomeric structural candidate is challenging because the stereochemical inversion of one chiral center among many centers does not always result in noticeable differences in their VCD spectra. This work demonstrates that the introduction of a suitable VCD chromophore with absorption in the 2300-1900 cm-1 region can be used for extracting local stereochemical information and for the stereochemical assignment of the C-1 position of various sugars as a case study. Through studies on a series of epimeric pairs of monosaccharides and their derivatives, we found that the introduction of one -OCD3 group to each C-1 position produced almost mirror-image VCD patterns in the 2300-1900 cm-1 region depending on the C-1 stereochemistry irrespective of the other molecular moieties. This work also shows that comparison of the observed VCD signals and the calculated ones enables the stereochemical assignment of a chiral center in the vicinity of the chromophore. This study provides a proof of concept that the use of a VCD chromophore in the 2300-1900 cm-1 region enables the analysis of selected stereochemistry of suitable molecular systems. Further studies on this concept should lead to the development of a method useful for the structural elucidation of other types of complex molecules.

Synthesis of Glycosyl Fluorides by Photochemical Fluorination with Sulfur(VI) Hexafluoride

This study describes a new convenient method for the photocatalytic generation of glycosyl fluorides using sulfur(VI) hexafluoride as an inexpensive and safe fluorinating agent and 4,4′-dimethoxybenzophenone as a readily available organic photocatalyst. This mild method was employed to generate 16 different glycosyl fluorides, including the substrates with acid and base labile functionalities, in yields of 43%-97%, and it was applied in continuous flow to accomplish fluorination on an 7.7 g scale and 93% yield.

Total Synthesis of Phospholipomannan of Candida albicans

First, total synthesis of the cell surface phospholipomannan anchor [β-Manp-(1 → 2)-β-Manp]n-(1 → 2)-β-Manp-(1 → 2)-α-Manp-1 → P-(O → 6)-α-Manp-(1 → 2)-Inositol-1-P-(O → 1)-phytoceramide of Candida albicans is reported. The target phospholipomannan (PLM) anchor poses synthetic challenges such as the unusual kinetically controlled (1 → 2)-β-oligomannan domain, anomeric phosphodiester, and unique phytoceramide lipid tail linked to the glycan through a phosphate group. The synthesis of PLM anchor was accomplished using a convergent block synthetic approach using three main appropriately protected building blocks: (1 → 2)-β-tetramannan repeats, pseudodisaccharide, and phytoceramide-1-H-phosphonate. The most challenging (1 → 2)-β-tetramannan domain was synthesized in one pot using the preactivation method. The phytoceramide-1-H-phosphonate was synthesized through an enantioselective A3 three-component coupling reaction. Finally, the phytoceramide-1-H-phosphonate moiety was coupled with pseudodisaccharide followed by deacetylation to produce the acceptor, which on subsequent coupling with tetramannosyl-H-phosphonate provided the fully protected PLM anchor. Final deprotection was successfully achieved by Pearlman's hydrogenation.

Total Synthesis of Tiacumicin B: Implementing Hydrogen Bond Directed Acceptor Delivery for Highly Selective β-Glycosylations

A total synthesis of tiacumicin B, a natural macrolide whose remarkable antibiotic properties are used to treat severe intestinal infections, is reported. The strategy is in part based on the prior synthesis of the tiacumicin B aglycone, and on the decisive use of sulfoxides as anomeric leaving groups in hydrogen-bond-mediated aglycone delivery (HAD). This new HAD variant permitted highly β-selective rhamnosylation and noviosylation. To increase convergence, the rhamnosylated C1–C3 fragment thus obtained was anchored to the C4–C19 aglycone fragment by adapting the Suzuki–Miyaura cross-coupling used for the aglycone synthesis. Ring-size-selective macrolactonization provided a compound engaged directly in the noviolysation step with virtually total β selectivity. The final efficient removal of all the protecting groups provided synthetic tiacumicin B.

A Synthetic Carbohydrate-Protein Conjugate Vaccine Candidate against Klebsiella pneumoniae Serotype K2

Klebsiella pneumoniae causes pneumonia and liver abscesses in humans worldwide and contains virulence factor capsular polysaccharides and lipopolysaccharides linked to the cell wall. Although capsular polysaccharides are good antigens for vaccine producti

Synthesis and cellular uptake of carbamoylated mannose derivatives

A series of 3-carbamoyl- and 2,3-dicarbamoyl-mannose derivatives were synthesized, conjugated to a fluorescent dye (Cy5GE, AF 647 or NBD) and their cellular uptake in A549 and THP-1 cell lines was studied by FACS. In contrast to earlier studies on carbamoyl mannosides, the observed uptake was not related to carbamoyl group on the mannose residue but rather to the cyanine dye attached, a trend previously observed for Cy5-fructose conjugates. The NBD-conjugates however, showed a temperature and concentration dependent uptake in case of mannose conjugates. These results suggest a profound impact of the dye which should be taken into consideration when studying the uptake of small molecules by dye conjugation.

ANTIBODY CONJUGATES AND METHODS OF MAKING THE ANTIBODY CONJUGATES

Described herein are antibody conjugates and methods of making antibody conjugates.

Efficient one-pot per-: O -acetylation-thioglycosidation of native sugars, 4,6- O -arylidenation and one-pot 4,6- O -benzylidenation-acetylation of S -/ O -glycosides catalyzed by Mg(OTf)2

A sequential one-pot per-O-acetylation-S-/O-glycosidation of native mono and disaccharides under solvent free conditions using 0.5 mole% of Mg(OTf)2 as a non-hygroscopic, recyclable catalyst is reported. Regioselective 4,6-O-arylidenation of glycosides and thioglycosides with benzaldehyde or p-methoxybenzaldehyde dimethyl acetal is catalyzed by 10 mole% of Mg(OTf)2 to produce the corresponding 4,6-O-arylidenated product in high yields. Mg(OTf)2 can also mediate sequential one-pot benzylidenation-acetylation of mono and disaccharide based glycosides and thioglycosides in high yield.