20672-69-9

Upstream product

• 16697-49-7 3,4,6-tri-O-benzyl-1,2-O-(methoxyethylidene)-β-D-mannopyranose 
• 108-98-5 thiophenol 
• 146864-77-9 3,4,6-tri-O-benzyl-1,2-O-(exo-methoxyethylidene)-β-D-mannopyranose 
• 68681-00-5 3,4,6-tri-O-benzyl-1,2-O-<1-(R)-methoxyethylidene>-β-D-mannopyranose 
• 100-44-7 benzyl chloride 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 124684-91-9 2-O-acetyl-3,4,6-tri-O-benzyl-1-deoxy-α-D-mannopyranosyl fluoride 
• 34234-44-1 methyl 2,3,4-tri-O-benzoylglucopyranoside 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 57-88-5 cholesterol 
• 768-95-6 1-adamanthanol 
• 821-09-0 n-Pent-4-enyl alcohol 
• 2216-51-5 (-)-menthol 
• 67-56-1 methanol 

Downstream Products

• 20672-67-7 methyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside 
• 767340-70-5 1-(3',4',6'-tri-O-benzyl-α-D-mannopyranosyl)prop-2-ene 
• 767340-68-1 methyl 2-O-allyl(dimethyl)silanyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside 
• 767340-69-2 methyl 2-O-tert-butyl(dimethyl)silanyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside 
• 767340-75-0 (1'E)-methyl 3,4,6-tri-O-benzyl-2-O-[dimethyl-(3'-trimethylsilanyl)prop-1'-enyl]silanyl-α-D-mannopyranoside 
• 767340-76-1 (1'E)-methyl 3,4,6-tri-O-benzyl-2-O-[diethyl-(3'-trimethylsilanyl)prop-1'-enyl]silanyl-α-D-mannopyranoside 
• 767340-77-2 (1'E)-methyl 3,4,6-tri-O-benzyl-2-O-[diisopropyl-(3'-trimethylsilanyl)prop-1'-enyl]silanyl-α-D-mannopyranoside 
• 192929-33-2 1-(3',4',6'-tri-O-benzyl-β-D-mannopyranosyl)prop-2-ene 
• 80585-62-2 methyl O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1<*>2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside 
• 80596-05-0 methyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1<*>2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside 
• 80585-63-3 methyl 2-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside 
• 80596-06-1 methyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside 
• 138566-33-3 C₆₂H₆₂O₁₃ 
• 138566-36-6 (2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-2-((2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-6-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-pyran-3-ol 

Relevant academic research and scientific papers

Glycosyl Exchange of Unactivated Glycosidic Bonds: Suppressing or Embracing Side Reactivity in Catalytic Glycosylations

While developing boron-catalyzed glycosylations using glycosyl fluoride donors and trialkylsilyl ether acceptors, competing pathways involving productive glycosylation or glycosyl exchange were observed. Experimental and computational mechanistic studies suggest a novel mode of reactivity where a dioxolenium ion is a key intermediate that promotes both pathways through addition to either a silyl ether or to the acetal of an existing glycosidic linkage. Modifications in catalyst structure enable either pathway to be favored, and with this understanding, improved multicomponent iterative couplings and glycosyl exchange processes were demonstrated.

Fluoride Migration Catalysis Enables Simple, Stereoselective, and Iterative Glycosylation

Challenges in the assembly of glycosidic bonds in oligosaccharides and glycoconjugates pose a bottleneck in enabling the remarkable promise of advances in the glycosciences. Here, we report a strategy that applies unique features of highly electrophilic b

AuIII-halide/phenylacetylene-catalysed glycosylations using 1-o-acetylfuranoses and pyranose 1,2-orthoesters as glycosyl donors

1-O-Acetylfuranoses and pyranose 1,2-orthoesters were activated with an AuIII halide/phenylacetylene relay catalyst system, and they acted as excellent glycosyl donors. Thus, 1-O-acetyl-D-ribofuranose, 1-O-acetyl-D-lyxofuranose, and 1,2-orthoesters selectively gave the corresponding 1,2-trans glycosides, whereas 1-O-acetyl-D-arabinofuranose and 1-O-acetyl-D-xylofuranose both gave mixtures of 1,2-trans and 1,2-cis glycosides, with the 1,2-trans glycosides predominating. A new glycosylation method has been developed for 1-O-acetylfuranoses and pyranose 1,2-orthoesters, using AuIII halides and phenylacetylene as relay catalyst systems. Good anomeric selectivity was observed for 1-O-acetylfuranoses, and excellent selectivity was observed for pyranose 1,2-orthoesters. The corresponding glycosides were formed in moderate to good yields.

A concise synthesis of single components of partially sulfated oligomannans

A concise synthesis of single components of C2 sulfated oligomannans including trimers, tetramers, and pentamers is reported. The synthesis features the application of the DMF-modulation method for the participatory thiomannoside donors in 1,2-trans α-glycosidic bond formation. The obtained oligomannans were fully characterized using 1H, 13C, COSY, and HSQC NMR spectroscopy.

Methyltrioxorhenium-catalyzed epoxidation-methanolysis of glycals under homogeneous and heterogeneous conditions

The efficient and high yielding domino epoxidation-methanolysis of glycals 8-15 has been achieved by oxidation with UHP in MeOH catalyzed by MTO. The products have been conveniently isolated as 2-acetoxy derivatives 16-23a, b by direct acetylation of the crude mixtures. Homogeneous MTO-amine complexes 5-7, heterogeneous poly(4-vinyl-pyridine)/MTO compounds I-III, and microencapsulated polystyrene/MTO systems IV-VII were also tested and demonstrated their effectiveness as catalysts for the oxidation step. The facial diastereoselectivity of the oxidation ranged from satisfactory to excellent depending on the substrate and could be optimized by ample screening of catalysts. Complete conversions of substrates and nearly quantitative yields of products were obtained under environmentally friendly experimental conditions and with the use of simple work-up procedures.

Stereoselective synthesis of allyl-C-mannosyl compounds: Use of a temporary silicon connection in intramolecular allylation strategies with allylsilanes

Methyl mannoside 16 containing an allyldimethylsilyl ether at C(2) was synthesized in nine steps from D-mannose. Reaction with TMSOTf in MeCN at room-temperature effected C-glycosylation to provide the α-allyl-C- mannosyl product 18 with excellent stereos

Synthesis of Thio-Linked Disaccharides by 1→2 Intramolecular Thioglycosyl Migration: Oxacarbenium versus Episulfonium Ion Intermediates

The conversion of 1,1′-thio-linked glucopyranosyl α-D-mannopyranosides to 1,2-thio-linked methyl sophorosides or methyl kojibiosides is described. The method involves the 1→2-migration of the thioglucopyranosyl portion of the nonreducing disaccharide with inversion of configuration at C-2 of the mannopyranose ring and concomitant formation of the methyl glucopyranoside. The thioglucosyl migration does not occur when electron-withdrawing benzoate protecting groups are present. The rearrangement occurs with retention of configuration in the migrating thioglucoside but the methyl glycoside is formed as a mixture of α- and β-isomers. This is attributed to a mechanism involving an oxacarbenium-ion intermediate rather than an episulfonium-ion intermediate. The relevance of this work to recent theoretical predictions concerning the relative stability of such intermediates is discussed.

A new method for the deprotection of benzyl ethers or the selective protection of alcohols

A new selective method for the deprotection of benzyl ethers situated next to alcohols in the α, β, or γ position is presented which uses either NIS or DIB/I2 as a reagent. After initial formation of a hypoiodite intermediate, the reaction is b

Glycosylation using a one-electron-transfer, homogeneous reagent. Application to an efficient synthesis of the trimannosyl core of N-glycosylproteins

Double glycosylation of methyl 2,4-di-O-benzyl-β-D-mannopyranoside with ethyl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside using as promoter tris(4-bromophenyl)ammoniumyl hexachloroantimonate, a stable, commercial, and crystalline radical cat

Synthesis and Conformational Analysis of Methyl 2-O-(α-D-Mannopyranosyl)-α-D-mannopyranoside

NMR experiments such as steady state NOE experiments and spin lattice 1H relaxation time measurements were performed on the synthetic disaccharide 10 that constitutes part of the polysaccharide backbone in fungal mannans.The spectroscopic data were compar