127299-77-8

Basic information

• Product Name: a-D-Mannopyranoside, phenyl 3,4,6-tris-O-(phenylMethyl)-1-thio-
• Synonyms: a-D-Mannopyranoside, phenyl 3,4,6-tris-O-(phenylMethyl)-1-thio-
• CAS NO: 127299-77-8
• Molecular Formula: C₃₃H₃₄O₅S
• Molecular Weight: 542.68506
• Mol File: 127299-77-8.mol
• Article Data: 31

Chemical Properties

• Appearance: /
• CAS DataBase Reference: a-D-Mannopyranoside, phenyl 3,4,6-tris-O-(phenylMethyl)-1-thio-(CAS DataBase Reference)
• NIST Chemistry Reference: a-D-Mannopyranoside, phenyl 3,4,6-tris-O-(phenylMethyl)-1-thio-(127299-77-8)
• EPA Substance Registry System: a-D-Mannopyranoside, phenyl 3,4,6-tris-O-(phenylMethyl)-1-thio-(127299-77-8)

Safety Data

• Hazardous Substances Data: 127299-77-8(Hazardous Substances Data)

Upstream product

• 930-69-8 sodium thiophenolate 
• 74372-90-0 3,4,6-tri-O-benzyl-D-glucal epoxide 
• 4670-62-6 tetra-N-butylammonium benzenethiolate 
• 152871-96-0 phenyl 1-deoxy-2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 211947-53-4 (2S,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(phenylthio)tetrahydro-2H-pyran-3-yl benzoate 
• 67-56-1 methanol 
• 350985-71-6 phenyl 3,4,6-tri-O-benzyl-2-O-(1-para-methoxyphenylethenyl)-1-thio-β-D-glucopyranoside 
• 2936-70-1 (2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 
• 100-39-0 benzyl bromide 
• 350985-70-5 phenyl 3,4,6-tri-O-benzyl-2-O-para-methoxybenzoyl-1-thio-β-D-glucopyranoside 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 20672-66-6 3,4,6-tri-O-benzyl-D-glucopyranose 
• 250273-77-9 1,2-Di-O-benzoyl-3,4,6-tri-O-benzyl-D-glucopyranose 
• 79218-68-1 2-O-acetyl-3,4,6-tri-O-benzyl-D-glucopyranose 

Downstream Products

• 116454-02-5 1,5-Anhydro-3,4,6-tri-O-benzyl-1,2-didesoxy-2-phenylthio-D-arabino-hex-1-enitol 
• 141810-68-6 methyl 2,3,4-tri-O-benzyl-6-O-(3,4,6-tri-O-benzyl-2-deoxy-2-phenylthio-β-D-glucopyranosyl)-β-D-galactopyranoside 
• 1083236-82-1 phenyl 2-O-tert-butoxycarbonyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside 
• 1192142-77-0 phenyl 2,4,6-tri-O-benzyl-3-O-(4-methoxyphenyl)methyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-1-thio-α-D-mannnopyranoside 
• 1192142-79-2 phenyl 2,3,4-tri-O-benzyl-6-O-(4-methoxyphenyl)methyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-tri-chloroacetamido-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-1-thio-α-D-mannnopyranoside 
• 205987-04-8 methyl 3,4,6-tri-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside S5 
• 1380315-30-9 C₅₉H₆₃N₃O₁₁ 
• 1380315-29-6 C₅₉H₆₃N₃O₁₁ 

Relevant articles and documents

Chemoenzymatic glycan-selective remodeling of a therapeutic lysosomal enzyme with high-affinity M6P-glycan ligands. Enzyme substrate specificity is the name of the game

Functionalization of therapeutic lysosomal enzymes with mannose-6-phosphate (M6P) glycan ligands represents a major strategy for enhancing the cation-independent M6P receptor (CI-MPR)-mediated cellular uptake, thus improving the overall therapeutic effica

α-Selective Glycosylation with β-Glycosyl Sulfonium Ions Prepared via Intramolecular Alkylation

Stereoselective glycosylation remains the main challenge in the chemical synthesis of oligosaccharides. Herein we report a simple method to convert thioglycosides into β-sulfonium ions via an intramolecular alkylation reaction, leading to highly α-selective glycosylations for a variety of glycosyl acceptors. The influence of the thioglycoside substituent and the protecting group pattern on the glycosyl donor was investigated and showed a clear correlation with the observed stereoselectivity.

Application of 2-substituted benzyl groups in stereoselective glycosylation

The use of 2-O-(2-nitrobenzyl) and 2-O-(2-cyanobenzyl) groups controls stereoselective formation of 1,2-trans-glycosidic linkages via the arming participation effect. The observed stereoselectivity likely arises from the intramolecular formation of cyclic intermediate between the electron-rich substituent and the donor oxacarbenium ion providing the expected facial selectivity for attack of the glycoside acceptor. The stereodirecting effect of the 2-nitro- and 2-cyanobenzyl groups attached at the remote position (C-3, C-4, and C-6) of the donor molecule have also been investigated. To prove the postulated mechanism based on the participation effect of 2-substituted benzyl groups in the glycosylation stereoselectivity we used DFT theoretical calculation methodology.