320576-38-3

Upstream product

• 320576-31-6 2,6-anhydro-1,3,4-tri-O-benzyl-5-O-[tert-butyl(dimethyl)silyl]-7,8-dideoxy-D-glycerol-L-gulo-nonitol 
• 320576-33-8 [[(5S,7S,8S,9S,10R)-8,9-bis(benzyloxy)-7-[(benzyloxy)methyl]-1,6-dioxaspiro[4,5]dec-10-yl]oxy](tert-butyl)dimethylsilane 
• 320576-36-1 (5R,7S,8S,9S,10R)-8,9-bis(benzyloxy)-7-[(benzyloxy)methyl]-1,6-dioxaspiro[4,5]decan-10-ol 
• 157794-06-4 2,6-anhydro-1,3,4-tri-O-benzyl-5-O-[tert-butyl(dimethyl)silyl]-7,8,9-trideoxy-D-glycerol-L-gulo-non-8-enitol 
• 157903-84-9 3-(3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-1-propene 
• 797010-94-7 Methanesulfonic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-tetrahydro-pyran-3-yl ester 
• 797010-96-9 Methanesulfonic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-hydroxy-propyl)-tetrahydro-pyran-3-yl ester 
• 797010-98-1 (2R,3R,4R,4aR,8aS)-3,4-Bis-benzyloxy-2-benzyloxymethyl-octahydro-pyrano[3,2-b]pyran 
• 320576-37-2 (5R,7S,8S,9S,10R)-8,9-bis(benzyloxy)-7-[(benzyloxy)methyl]-1,6-dioxaspiro[4,5]decan-10-yl methanesulfonate 
• 161275-25-8 3-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-1-propene 
• 288584-96-3 3-C-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)1-propanol 

Relevant academic research and scientific papers

Diisobutylaluminium hydride (DIBAL-H) as a molecular scalpel: A new mechanistic proposal for a spiroketal rearrangement

Taking advantage of our knowledge of the capacity of DIBAL-H to de-O-alkylate, we propose an alternative mechanism for a spiroketal rearrangement described by E. Suàrez. We also show that this proposal can account for the formation of the secondary product, whose original structure we propose to correct.