440362-96-9

Upstream product

• 288584-96-3 3-C-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)1-propanol 
• 161275-25-8 3-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-1-propene 
• 157903-84-9 3-(3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-1-propene 
• 193546-84-8 3-C-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glycopyranosyl)propene 

Downstream Products

• 440362-88-9 Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-triisopropylsilanyloxy-propyl)-tetrahydro-pyran-3-yl ester 
• 440362-97-0 Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-oxo-propyl)-tetrahydro-pyran-3-yl ester 
• 440362-87-8 (2S,3S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-butenyl)-tetrahydro-pyran-3-acetate 
• 440362-89-0 (2R,3R,4S,5S,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-but-3-enyl-5-isopropenyloxy-tetrahydro-pyran 

Relevant academic research and scientific papers

1,5-Hydrogen Atom Transfer/Surzur-Tanner Rearrangement: A Radical Cascade Approach for the Synthesis of 1,6-Dioxaspiro[4.5]decane and 6,8-Dioxabicyclo[3.2.1]octane Scaffolds in Carbohydrate Systems

The 1,5-HAT-1,2-(ester)alkyl radical migration (Surzur-Tanner rearrangement) radical/polar sequence triggered by alkoxyl radicals has been studied on a series of C-glycosyl substrates with 3-C-(α,β-d,l-glycopyranosyl)1-propanol and C-(α-d,l-glycopyranosyl)methanol structures prepared from chiral pool d- and l-sugar. The use of acetoxy and diphenoxyphosphatoxy as leaving groups provides an efficient construction of 10-deoxy-1,6-dioxaspiro[4.5]decane and 4-deoxy-6,8-dioxabicyclo[3.2.1]octane frameworks. The alkoxyl radicals were generated by the reaction of the corresponding N-alkoxyphthalimides with group 14 hydrides [n-Bu3SnH(D) and (TMS)3SiH], and in comparative terms, the reaction was also initiated by visible light photocatalysis using the Hantzsch ester/fac-Ir(ppy)3 procedure. Special attention was devoted to the influence of the relative stereochemistry of the centers involved in the radical sequence on the reaction outcome. The addition of BF3?Et2O as a catalyst to the radical sequence resulted in a significant increase in the yields of the desired bicyclic ketals.

C-Glycosides to fused polycyclic ethers

This manuscript describes the synthesis of fused polycyclic ethers from the coupling of C-glycoside forming reactions with ring closing metathesis and acid mediated annulation reactions.