97275-50-8

Upstream product

• 67-56-1 methanol 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 37776-25-3 2,3,5-tri-O-benzyl-D-arabinose 
• 4455-77-0 (methoxymethyl)diphenylphosphine oxide 
• 160549-10-0 2,3,5-tri-O-benzyl-D-arabinofuranose 

Downstream Products

• 845828-84-4 (E)-(3R,4R)-1,3,4-Tris-benzyloxy-6-methoxy-hex-5-en-2-one oxime 
• 845828-94-6 (E,2R,3R)-2,3-bis(benzyloxy)-5-methoxypent-4-enenitrile 
• 845829-01-8 (2R,3R)-2,3-Bis-benzyloxy-5-oxo-pentanenitrile 
• 20672-67-7 methyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside 
• 40246-30-8 methyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside 

Relevant academic research and scientific papers

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.

A NEW ENTRY INTO VERSATILE RING OPENING OF O-BENZYL GLYCALS AND RELATED COMPOUNDS via Tl(NO3)3 and NaBH4

A new, one pot procedure for the preparation of chiral building blocks, by treatment of O-benzyl glycals 10, 11, 12 and cyclic enol-ethers 1, 3 and 7 with the system Tl(NO3)3 and NaBH4 described.

Formation of Glycosides by Epoxidation-Ring Closure of Open-chain Hydroxyenol Ethers obtained from Sugars

Z- and E-Hydroxyenol ethers, obtained from aldopentoses by a Horner-Wittig reaction, have been epoxidized using m-chloroperbenzoic acid or t-butyl hydroperoxide.A spontaneous intramolecular cyclization of the intermediate epoxides due to the free hydroxy

A NOVEL APPROACH TO THE SYNTHESIS OF 1,2-cis-GLYCOPYRANOSIDES

Methyl 3,4,6-tri-O-benzyl-α-D-glucopyranoside and methyl 3,4,6-tri-O-benzyl-β-D-mannopyranoside were directly obtained by m-chloroperbenzoic acid treatment of (Z)-(2R,3R,4R)-6-methoxy-1,3,4-tribenzyloxy-5-hexen-2-ol.