116809-49-5

Upstream product

• 116809-48-4 methyl 4-O-benzoyl-2,3-di-O-toluene-p-sulfonyl-6-deoxy-α-D-glucopyranoside 
• 101155-76-4 methyl 2,3-di-O-p-toluenesulfonyl-4-O-benzoyl-6-bromo-6-deoxy-α-D-glucopyranoside 
• 116809-47-3 Benzoic acid (2S,3R,4S,5R,6S)-2-iodomethyl-6-methoxy-4,5-bis-(toluene-4-sulfonyloxy)-tetrahydro-pyran-3-yl ester 

Downstream Products

• 116907-46-1 (3R,4R,6R)-6-Methyl-tetrahydro-pyran-2,3,4-triol 
• 101155-81-1 methyl 2-O-p-toluenesulfonyl-4,6-dideoxy-α-D-ribo-hexopyranoside 

Relevant academic research and scientific papers

Total Synthesis of (+)-Colletodiol: New Methodology for the Synthesis of Macrolactones

Synthetic efforts directed toward two different structures suggested for the macrocyclic bis(lactone) colletodiol are detailed.The initial approach to an incorrect structure (C11 epi) relies upon the manipulation of methyl α-D-glucopyranoside to set the required stereochemistry for the C8-C14 segment of the C11 epi structure.The second approach, initiated after structural revision based upon X-ray crystallographic evidence, employs a Lewis acid mediated addition of allylstannane 33 to β-alkoxy aldehyde 34 to set the stereochemistry of the C8-C14 subunit.This route, which employs a number of new synthetic reactions developed specifically for this problem, gives (+)-colletodiol in nine linear operations and 8.2percent overall yield.