117467-65-9

Upstream product

• 100-39-0 benzyl bromide 
• 136764-17-5 3'-Phenyl-2',3'-methanopropyl 2-O-<<(trifluoromethyl)sulfonyl>oxy>-3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 136764-32-4 (2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((1S,2S)-2-phenyl-cyclopropylmethoxy)-tetrahydro-pyran-3-ol 
• 129116-33-2 3,4,6-tri-O-benzyl-2,5-anhydro-D-mannose dimethylacetal 
• 114117-12-3 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-1,5-anhydro-2-deoxy-3,6-di-O-benzyl-D-arabino-hex-1-enitol 
• 94273-27-5 2,5-anhydro-3,4,6-tris-O-(phenylmethyl)-D-mannose 
• 41107-82-8 2,5-anhydro-D-mannitol 
• 102208-55-9 2,5-anhydro-3,4,6-tri-O-benzyl-D-mannitol 
• 198775-13-2 ((3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-methanol 

Downstream Products

• 222555-96-6 2,5-anhydro-3,4-di-O-benzyl-D-mannitol 
• 878675-41-3 [(S)-1-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-hexadecyloxymethyl-tetrahydro-furan-2-ylmethyl)-pyrrolidin-2-yl]-methanol 
• 878675-40-2 ((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-hexadecyloxymethyl-tetrahydro-furan-2-yl)-methanol 

Relevant academic research and scientific papers

Hydrolytically stable arabinofuranoside analogs for the synthesis of arabinosyltransferase inhibitors

The first members of two new families of arabinosyltransferase inhibitors, derived from previously reported hybrid compounds covalently associating an iminoalditol with an α-d-arabinofuranoside, have been prepared. In place of the arabinofuranoside moiety

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.

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

REACTION BETWEEN GLYCAL BENZYL ETHERS AND THALLIUM(III) NITRATE. SYNTHESIS OF SHOWDOMYCIN ANALOGUES.

On treatment with thallium(III) nitrate, trihydrate in acetonitrile solution, 3,4,6-tri-O-benzyl-D-glucal (5) gives the ring-contracted aldehyde (6) which has been converted into the showdomycin analogue (8) ; 2-(α-D-2'-deoxyribofuranosyl)maleimide (12) h