314740-77-7

Upstream product

• 358-23-6 trifluoromethylsulfonic anhydride 
• 218937-71-4 ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 
• 156397-47-6 trifluoromethanesulfonyloxy(triphenylphosphine)gold(I) 
• 20770-84-7 2,3-di-O-benzyl-4,6-O-benzylidene-α/β-D-mannopyranose 
• 1493-13-6 trifluorormethanesulfonic acid 
• 1037510-22-7 C₃₅H₃₁O₉^(1-) 
• 159407-17-7 phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 
• 84224-65-7 benzenesulfenyl triflate 

Downstream Products

• 1072522-97-4 2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-(2-oxo-2-phenylethyl)-β-D-mannopyranose 
• 412922-95-3 benzyl 4,8,12,16,20-pentamethylpentacosylphosphoryl 2,3-di-O-benzyl-4,6-O-benzylidene-β-mannopyranoside 
• 354986-52-0 methyl 2-acetamido-2-deoxy-4-O-benzyl-3-O-(2-picolinyl)-[2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl]-(1->6)-α-D-glucopyranoside 
• 316187-61-8 benzyl 3,7,11,15-tetramethylhexadecylphosphoryl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranoside 

Relevant academic research and scientific papers

β-Mannosylation with 4,6-benzylidene protected mannosyl donors without preactivation

Mannosylations with benzylidene protected mannosyl donors were found to be β-selective even when no preactivation was performed. It was also found that the kinetic β-product in some cases anomerizes fast to the thermodynamically favored α-anomer under typical reaction conditions.

Highly stereoselective β-mannopyranosylation via the 1-α-glycosyloxy-isochromenylium-4-gold(I) intermediates

While the gold(I)-catalyzed glycosylation reaction with 4,6-O-benzylidene tethered mannosyl ortho-alkynylbenzoates as donors falls squarely into the category of the Crich-type β-selective mannosylation when Ph3PAuOTf is used as the catalyst, in that the mannosyl α-triflates are invoked, replacement of the -OTf in the gold(I) complex with less nucleophilic counter anions (i.e., -NTf2, -SbF6, -BF4, and -BAr4F) leads to complete loss of β-selectivity with the mannosyl ortho-alkynylbenzoate β-donors. Nevertheless, with the α-donors, the mannosylation reactions under the catalysis of Ph3PAuBAr4F (BAr4F=tetrakis[3,5-bis(trifluoromethyl)phenyl]borate) are especially highly β-selective and accommodate a broad scope of substrates; these include glycosylation with mannosyl donors installed with a bulky TBS group at O3, donors bearing 4,6-di-O-benzoyl groups, and acceptors known as sterically unmatched or hindered. For the ortho-alkynylbenzoate β-donors, an anomerization and glycosylation sequence can also ensure the highly β-selective mannosylation. The 1-α-mannosyloxy-isochromenylium-4-gold(I) complex (Cα), readily generated upon activation of the α-mannosyl ortho-alkynylbenzoate (1 α) with Ph3PAuBAr4F at -35 C, was well characterized by NMR spectroscopy; the occurrence of this species accounts for the high β-selectivity in the present mannosylation.

Influence of O6 in mannosylations using benzylidene protected donors: Stereoelectronic or conformational effects?

The stereoselective synthesis of β-mannosides and the underlying reaction mechanism have been thoroughly studied, and especially the benzylidene-protected mannosides have gained a lot of attention since the corresponding mannosyl triflates often give exce

Direct glycosylation with anomeric hydroxy sugars by activation with 3-fluorophthalic anhydride and trifluoromethanesulfonic anhydride

An efficient and direct one-pot glycosylation method using anomeric hydroxy sugars as glycosyl donors, employing 3-fluorophthalic anhydride and triflic anhydride as activating agents, has been developed. The present glycosylation utilizing 3-fluorophthali

Is donor-acceptor hydrogen bonding necessary for 4,6-O-benzylidene-directed β-mannopyranosylation? stereoselective synthesis of β-C- mannopyranosides and α-C-glucopyranosides

(Equation Presented) 2,3-Di-O-benzyl-4,6-0-benzylidene-thiohexopyranosides: on activation with 1-benzenesulfinyl piperidine and triflic anhydride, react with allyl silanes and stannanes, and with silyl enolethers to give C-glycosides. In the mannose serie

Stereoselective direct glycosylation with anomeric hydroxy sugars by activation with phthalic anhydride and trifluoromethanesulfonic anhydride involving glycosyl phthalate intermediates

An efficient direct one-pot glycosylation method with anomeric hydroxy sugars as glycosyl donors employing phthalic anhydride and triflic anhydride as activating agents has been developed. Thus, highly stereoselective β-mannopyranosylations were achieved

Confirmation of the connectivity of 4,8,12,16,20-pentamethylpentacosylphoshoryl β-D-mannopyranoside, an unusual β-mannosyl phosphoisoprenoid from Mycobacterium avium, through synthesis

The synthesis of the title glycolipid is reported. Comparison of the electrospray and high-energy collision-induced dissociation mass spectra of the synthetic material with those reported for the isolate confirm the structure of this unusual antigenic substance with its modified isoprenoid chain.

1-Benzenesulfinyl piperidine/trifluoromethanesulfonic anhydride: A potent combination of shelf-stable reagents for the low-temperature conversion of thioglycosides to glycosyl triflates and for the formation of diverse glycosidic linkages

The combination of 1-benzenesulfinyl piperidine (BSP) and trifluoromethanesulfonic anhydride (Tf2O) forms a new, powerful, metal-free thiophile that can readily activate both armed and disarmed thioglycosides, via glycosyl triflates, in a matte

Efficient, diastereoselective chemical synthesis of a beta-mannopyranosyl phosphoisoprenoid.

[reaction: see text] Tetrabutylammonium benzyl dihydrophytylphosphate was coupled to S-phenyl 2,3-di-O-benyl-4, 6-O-benzylidene-1-thio-alpha-D-mannopyranoside S-oxide on activation with triflic anhydride in toluene at -78 degrees C to give the corresponding beta-mannosyl phosphate in 56% yield with no detectable formation of the alpha-anomer. Treatment with sodium in liquid ammonia then afforded the unprotected beta-mannosyl phosphoisoprenoid.

S-(4-methoxyphenyl) benzenethiosulfinate (MPBT)/ trifluoromethanesulfonic anhydride: A convenient system for the generation of glycosyl triflates from thioglycosides

(Matrix presented) The combination of S-(4-methoxyphenyl) benzenethiosulfinate (MPBT, 1) and trifluoromethanesulfonic anhydride forms a powerful, metal-free, thiophile which readily activates thioglycosides, via glycosyl triflates, at -60°C in dichloromet