142393-19-9

Upstream product

• 131389-37-2 tert-Butyl-((2R,4aR,6S,7R,8S,8aR)-7-methoxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-dimethyl-silane 
• 101696-02-0 phenyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside 
• 71676-30-7 phenyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 142270-08-4 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-O-methyl-β-D-glucopyranosyl phenyl sulfone 
• 71676-30-7 (2R,4aR,6S,7R,8R,8aS)-2-Phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 
• 331456-79-2 Phenyl 2,3-bis-O-(O-tert-butyldimethylsilyl)-4,6-O-benzylidene-1-thio-β-D-glucopyronaside 
• 331456-80-5 2,3-Di-O-(tert-butyldimethylsilyl)-4,6-O-benzylidene-β-D-xylopyranosyl phenyl sulfone 

Relevant academic research and scientific papers

Copper(I)-mediated 1,2-metallate rearrangements of 1-metallated glycals

1,2-Metallate rearrangements involving reaction of 1-metallated glycals with organolithium reagents under copper(I) mediation give alkenylpolyol chains in 45-91% yield (19 examples). The reaction was applied to a formal synthesis of KRN7000 as well as a synthesis of a 5,6-ceramide derivative. Georg Thieme Verlag Stuttgart · New York.

The preparation of 1-tributylstannyl glycals from 1-phenylsulfonyl glycals via Ni(0)-catalysed coupling with tributylstannylmagnesium bromide

1-Phenylsulfonyl glycals undergo an easy Ni(0)-catalysed coupling with tributylstannylmagnesium bromide to give the corresponding 1-tributylstannyl glycals in good yield.

Synthesis of C-glycopyranosyl compounds by a palladium-catalyzed coupling reaction of 1-tributylstannyl-D-glucals with organic halides

1-Tributylstannyl-D-glucals, prepared from the corresponding 1-phenylsulfonyl-D-glucals, were coupled efficiently to various organic halides in the presence of a palladium(0) catalyst.This mild reaction is specially useful for the preparation of 1-C-aryl-

ARYLATION OF 1-TRIBUTYLSTANNYL GLYCALS CATALYZED BY PALLADIUM: A SYNTHETIC ROUTE TO THE BASIC SKELETON OF THE PAPULACANDINS AND CHAETIACANDIN

The palladium-catalyzed coupling reaction of 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-tri-n-butylstannyl-D-glucal 7 with 3,5-dibenzyloxy-2-bromo-benzyl alcohol 8 gave a 78percent yield of the C-arylated glycal 11, stereoselectivity transformed into