94273-27-5

Upstream product

• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 129173-16-6 3,6-anhydro-4,5,7-tri-O-benzyl-1,2-dideoxy-D-manno-hept-1-enitol 
• 102208-55-9 2,5-anhydro-3,4,6-tri-O-benzyl-D-mannitol 
• 222555-96-6 2,5-anhydro-3,4-di-O-benzyl-D-mannitol 
• 40246-30-8 methyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 53929-30-9 benzyl 3,4,6-tetra-O-benzyl-β-G-glucopyranoside 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 136764-17-5 3'-Phenyl-2',3'-methanopropyl 2-O-<<(trifluoromethyl)sulfonyl>oxy>-3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 68-12-2 N,N-dimethyl-formamide 
• 287733-97-5 (2S,3R,4R,5R)-1,3,4,5-Tetrakis-benzyloxy-hept-6-en-2-ol 
• 162239-11-4 (2S,3R,4R,5S)-1,3,4,5-Tetrakis-benzyloxy-hept-6-en-2-ol 
• 162239-12-5 3,6-anhydro-4,5,7-tri-O-benzyl-1,2-dideoxy-D-gluco-hept-1-enitol 
• 92619-92-6 3,4,5,7-tetra-O-benzyl-1,2-dideoxy-D-manno-hept-1-enitol 
• 79258-18-7 (2R,3R,4R,5S)-1,3,4,5-tetrakis(benzyloxy)hept-6-en-2-ol 

Downstream Products

• 126378-35-6 (S)-5-[(R)-((2R,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-hydroxy-methyl]-5H-furan-2-one 
• 126421-63-4 (R)-5-[(R)-((2R,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-hydroxy-methyl]-5H-furan-2-one 
• 117467-66-0 2-(α-D-arabinofuranosyl)maleimide 
• 16755-07-0 3-((2S,3S,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-pyrrole-2,5-dione 
• 102208-55-9 2,5-anhydro-3,4,6-tri-O-benzyl-D-mannitol 
• 492470-84-5 1-((2R,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-2-((2R,3R,4S,5S)-3,4-bis-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-2-nitro-ethanol 
• 583826-63-5 C₅₄H₅₆O₈ 
• 911292-63-2 N-{(1E)-[(2R,3R,4R,5R)-3,4-dibenzyloxy-5-(benzyloxymethyl)tetrahydrofuran-2-yl]methylene}-2-tert-butanesulfinamide 
• 911292-95-0 (2S,5R)-5-[(R)-Amino-((2R,3R,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-methyl]-2-tert-butyl-2,5-dimethyl-[1,3]dioxolan-4-one 
• 911292-96-1 (2S,5R)-5-[(R)-Amino-((2R,3R,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-methyl]-2-tert-butyl-5-phenyl-[1,3]dioxolan-4-one 
• 911292-70-1 2-Methyl-propane-2-sulfinic acid [(R)-((2R,3R,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-((2S,4R)-2-tert-butyl-2,4-dimethyl-5-oxo-[1,3]dioxolan-4-yl)-methyl]-amide 
• 911292-71-2 2-Methyl-propane-2-sulfinic acid [(R)-((2R,3R,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-((2S,4R)-2-tert-butyl-5-oxo-4-phenyl-[1,3]dioxolan-4-yl)-methyl]-amide 
• 109065-80-7 2,5-anhydro-3,4,6-tri-O-benzyl-1-deoxy-1-iodo-D-mannitol 
• 583826-67-9 C₇₄H₇₆O₁₁ 

Relevant academic research and scientific papers

A new synthetic approach to mycobacterial cell wall α-(1→5)-D-arabinofuranosyl C-oligosaccharides

Three designed arabinofuranose building blocks allowed the diastereoselective synthesis of a C-disaccharide and a C-trisaccharide by Wittig olefination. The latter compound represents the first example of all-carbon linked arabinofuranotriose analogue.

Rearrangements in the course of fluorination by diethylaminosulfur trifluoride at C-2 of glycopyranosides: Some new parameters

Reaction of a series of 21 glycosides unprotected at O-2 and featuring various configurations with DAST (diethylaminosulfur trifluoride) was monitored by 19F NMR spectroscopy. By means of the diacritical set of data (shift values and coupling c

First synthesis of methyl α-C-D-arabinofuranosyl-(1→5)-α-D-arabinofuranoside: The C-disaccharide segment of motif C of Mycobacterium tuberculosis

The synthesis of C-analogue of the disaccharide 2 α-araf-(1→5)-araf, present in motif C of the arabino-galactan portion of Mycobacterium tuberculosis, has been described. The critical C-C bond formation reaction to couple both the furanosyl residues has b

Synthesis of Selectively Labeled D-Fructose and D-Fructose Phosphate Analogues Locked in the Cyclic Furanose Form

2,5-Anhydroglucitol and 2,5-anhydromannitol and their 6-phosphate and 1,6-diphosphate derivatives are cyclic analogues of the α and β anomers of D-fructofuranose, D-fructofuranose-6-phosphate, and D-fructofuranose-1,6-diphosphate. They were synthesized from protected D-mannose or D-glucose. The synthetic method was developed with emphasis on selective 2H labeling of these compounds, as a model for 3H incorporation, which will be used for further biochemical studies. A key cyclization step, based on a benzyl ether nucleophilic attack on an activated alcohol, constructed the ring system. The stereochemistry at C2 (α/β anomers) and at C5 (D sugar) was controlled by selective epimerizations. Mono- and diphosphate analogues were obtained from the same intermediate by changing the sequence of deprotection and phosphorylation steps.

An unexpected rearrangement during Mitsunobu epimerization reaction of sugar derivatives

Mitsunobu reaction on the glucose derivative (3S,4R,5R,6R)-3,4,5,7- tetrabenzyloxy-6-hydroxy-1-heptene yielded an unexpected rearrangement major product. Its structure was determined as (3R,4R,5R,6S)-4,5,6,7- tetrabenzyloxy-3-hydroxy-1-heptene. The suggested rearrangement mechanism involves an initial intramolecular cyclization, followed by ring opening by the nucleophile p-nitrobenzoate. Product distribution of the Mitsunobu reaction was substrate-dependent, with the corresponding mannose derivative (the 3R epimer) giving less of the initial intramolecular reaction products and the corresponding galactose derivative (the 5S epimer) yielding almost exclusively the expected epimerization product. Varying the Mitsunobu reaction conditions (addition of base and using nonpolar solvent) led to the expected epimerization product of the glucose derivative.

Stereoselective synthesis of tetrahydrofurans and linear methyl enol- ethers from glycals

The O-benzyl derivatives of 1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol (D-glucal, 1), 1,5-anhydro-2,6-dideoxy-L-arabino-hex-1-enitol (L-rhamnal, 7), and 1,5-anhydro-2-deoxy-D-lyxo-hex-1-enitol (D-galactal, 9), underwent stereoselectively a ring contraction by treatment with thallium(III) nitrate (TTN) in MeOH, giving respectively the dimethylacetal derivatives of 3,4,6- tri-O-benzyl-2,5-anhydro-D-mannose, 3,4-di-O-benzyl-6-deoxy-2,5-anhydro-L- mannose (8) and 3,4,6-tri-O-benzyl-2,5-anhydro-D-talose (10). Conversely, the protected glycals 1, 7 and 9, underwent the ring opening reaction by action of the TTN-NaBH4 reagent in MeOH, providing the enantiomerically pure methyl enol-ethers 3,4,6-tri-O-benzyl-2-deoxy-1-O-methyl-D-arabino-hex-1-enitol, 3,4-di-O-benzyl-2,6-dideoxy-1-O-methyl-L-arabino-hex-1-enitol and 3,4,6-tri- O-benzyl-2-deoxy-1-O-methyl-D-lyxo-hex-1-enitol. The perbenzylated glycosyl- glycals, such as 3,6-di-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D- glucopyranosyl)-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol (cellobial) (16), 3,6-di-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-1,5- anhydro-2-deoxy-D-arabino-hex-1-enitol (lactal) (19) and 3,4-di-O-benzyl-6- O-(2, 3,4,6- tetra- O-benzyl- α-D-galactopyranosyl)- 1,5- anhydro-2-deoxy- D-arabino-hex-1-enitol (melibial) (22), showed the same reactivity as the corresponding glycals by reaction with TTN in MeOH, resulting selectively in the ring contracted compounds at the glycal moiety. The reaction with TTN- NaBH4 in MeOH, carried out on 16, 19 and 22, led to the formation of the open chain derivatives at the glycal site.

Chemistry of glucal halohydrins(II): An unusual protecting group effect in the competitive formation of formyl furanosides and methyl glycosides

A remarkable protecting group influence was observed in the base-induced reaction of protected halohydrins derived from D-glycals. Tri-O-methyl and tri-O-benzyl halohydrins react with cesium carbonate in methanol at room temperature to give methyl glycosides as the major product and unsaturated formyl furanosides as the minor product. Whereas, the tri-O-tert-butyldimethylsilyl (t-BuMe2Si)-protected halohydrins reacted with cesium carbonate in methanol at room temperature to give a mixture of epimeric formyl furanosides, and at reflux to give an unsaturated formyl furanoside, as the only products. The tri-O-methyl and tri-O-benzyl halohydrins react slowly at elevated temperature to give predominantly furans. In comparison, the tri-O-t-BuMe2Si halohydrins reacted completely after five minutes to give a mixture of epimeric formyl furanosides. The tri-O-t-BuMe2Si iodohydrins were oxidized to the corresponding iodolactones, which also underwent a based-induced ring contraction in methanol to give the furanose 1-methylcarboxylate esters.

Asymmetric Cyclopropanation of Allylic Ethers: Cleavage and Regeneration of the Chiral Auxiliary

The ring contraction reaction of 2-O-oxy>-β-D-glucopyranosides and their corresponding α-anomers is reported.The rearrangement was shown to occur under extremely mild basic conditions to allow isolation of acid-sensitive optica