65236-83-1

Basic information

• Product Name: Phenyl 1-thio-alpha-D-mannopyranoside 2,3,4,6-tetrabenzoate
• Synonyms: Phenyl 1-thio-alpha-D-mannopyranoside 2,3,4,6-tetrabenzoate
• CAS NO: 65236-83-1
• Molecular Weight: 688.755
• Mol File: 65236-83-1.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: Phenyl 1-thio-alpha-D-mannopyranoside 2,3,4,6-tetrabenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Phenyl 1-thio-alpha-D-mannopyranoside 2,3,4,6-tetrabenzoate(65236-83-1)
• EPA Substance Registry System: Phenyl 1-thio-alpha-D-mannopyranoside 2,3,4,6-tetrabenzoate(65236-83-1)

Safety Data

• Hazardous Substances Data: 65236-83-1(Hazardous Substances Data)

Upstream product

• 108-98-5 thiophenol 
• 108836-02-8 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl bromide 
• 96996-90-6 1,2,3,4,6-penta-O-benzoyl-α,β-D-mannopyranoside 
• 83-87-4 D-Mannose pentaacetate 
• 530-26-7 D-Mannose 
• 13992-16-0 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 
• 2936-70-1 (2R,3S,4S,5S,6R)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 
• 98-88-4 benzoyl chloride 
• 2592-58-7 1,2,3,4,6-penta-O-benzoyl-β-D-mannopyranose 
• 10257-28-0 D-Galactose 
• 93-97-0 benzoic acid anhydride 
• 121523-92-0 C₃₆H₃₀O₁₁ 
• 16758-34-2 1-thiophenyl-β-D-galactopyranoside 
• 618-32-6 Benzoyl bromide 

Downstream Products

• 159407-19-9 phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside 
• 549528-08-7 C₅₉H₆₈N₂O₁₃ 
• 549528-10-1 C₅₁H₅₂N₂O₁₃ 
• 549528-09-8 C₅₅H₆₀N₂O₁₃ 
• 1190749-46-2 3-azidopropyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->6)-[2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->3)]-2,4-di-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside 
• 1126292-28-1 (2S,4S)-2,4-bis(2',3',4',6'-tetra-O-benzoyl-α-D-mannopyranosyloxy)pentane 
• 1126292-27-0 (2R,4R)-2,4-bis(2',3',4',6'-tetra-O-benzoyl-α-D-mannopyranosyloxy)pentane 
• 1126292-30-5 2,4,6-tris(2',3',4',6'-tetra-O-benzoyl-α-D-mannopyranosyloxy)heptane 
• 1126292-23-6 (3R)-1,3-bis(2',3',4',6'-tetra-O-benzoyl-α-D-mannopyranosyloxy)butane 
• 1126292-25-8 (3S)-1,3-bis(2',3',4',6'-tetra-O-benzoyl-α-D-mannopyranosyloxy)butane 
• 1126292-20-3 (2R,3R)-2,3-bis(2',3',4',6'-tetra-O-benzoyl-α-D-mannopyranosyloxy)butane 
• 1126292-19-0 (2S,3R)-2,3-bis(2',3',4',6'-tetra-O-benzoyl-α-D-mannopyranosyloxy)butane 
• 1126292-22-5 (2S,3S)-2,3-bis(2',3',4',6'-tetra-O-benzoyl-α-D-mannopyranosyloxy)butane 
• 1126292-29-2 1,4-bis(2',3',4',6'-tetra-O-benzoyl-α-D-mannopyranosyloxy)butane 

Relevant articles and documents

Total Synthesis of a Partial Structure from Arabinogalactan and Its Application for Allergy Prevention

Arabinogalactan, a microheterogeneous polysaccharide occurring in plants, is known for its allergy-protective activity, which could potentially be used for preventive allergy treatment. New treatment options are highly desirable, especially in a preventive manner, due to the constant rise of atopic diseases worldwide. The structural origin of the allergy-protective activity of arabinogalactan is, however, still unclear and isolation of the polysaccharide is not feasible for pharmaceutical applications due to a variation of the activity of the natural product and contaminations with endotoxins. Therefore, a pentasaccharide partial structure was selected for total synthesis and subsequently coupled to a carrier protein to form a neoglycoconjugate. The allergy-protective activity of arabinogalactan could be reproduced with the partial structure in subsequent in vivo experiments. This is the first example of a successful simplification of arabinogalactan with a single partial structure while retaining its allergy-preventive potential.

In(III) triflate-mediated solvent-free synthesis and activation of thioglycosides by ball milling and structural analysis of long chain alkyl thioglycosides by TEM and quantum chemical methods

Conventional solution-phase synthesis of thioglycosides from glycosyl acetates and thiols in the presence of In(III) triflate as reported for benzyl thioglucoside failed when applied to the synthesis of phenolic and alkyl thioglycosides. But, it was achieved in high efficiency and diastereospecificity with ease by solvent-free grinding in a ball mill. The acetates in turn were also obtained by the homogenization of free sugars with stoichiometric amounts of acetic anhydride and catalytic In(OTf)3 in the mill as neat products. Per-O-benzylated thioglycosides on grinding with an acceptor sugar in the presence of In(OTf)3 yield the corresponding O-glycosides efficiently. The latter in the case of a difficult secondary alcohol was nearly exclusive (>98%) in 1,2-cis-selectivity. In contrast, the conventional methods for this purpose require use of a coreagent such as NIS along with the Lewis acid to help generate the electrophilic species that actually is responsible for the activation of the thioglycoside donor in situ. The distinctly different self-assembling features of the peracetylated octadecyl 1-thio-α- and β-d-galactopyranosides observed by TEM could be rationalized by molecular modeling.

Design, synthesis, and evaluation of β-galactosylceramide mimics promoting β-glucocerebrosidase activity in keratinocytes

We have established an efficient synthesis of mimics of β-galactosylceramide (β-GalCer) increasing a β-glucocerebrosidase (β-GlcCer'ase) activity that associates with the skin barrier function. Among the synthetic β-GalCer analogues (6a-6e) described herein, compound 6e exhibited a potent effect on the activation of β-GlcCer'ase function in vitro and reduced the transepidermal water loss (TEWL) level in a UVB-induced barrier disrupted mice model. These findings indicated that compound 6e could be useful for cosmetics and medicines to improve skin barrier function.