118916-55-5

Upstream product

• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 118798-68-8 2,6-Anhydro-1,3,4-tri-O-benzyl-5,8,9-tridesoxy-5-phenylsulfinyl-L-gulo-non-5-enitol 
• 118798-67-7 1,5-Anhydro-3,4,6-tri-O-benzyl-1,2-didesoxy-2-phenylsulfinyl-D-arabino-hex-1-enitol 
• 108-24-7 acetic anhydride 
• 116558-79-3 2,6-Anhydro-1,3,4-tri-O-benzyl-8,9-didesoxy-L-gulo-L-erythro-nonitol 
• 116454-02-5 1,5-Anhydro-3,4,6-tri-O-benzyl-1,2-didesoxy-2-phenylthio-D-arabino-hex-1-enitol 
• 116558-78-2 2,6-Anhydro-1,3,4-tri-O-benzyl-5,8,9-tridesoxy-L-gulo-non-5-enitol 
• 116454-08-1 (3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((S)-1-hydroxy-propyl)-tetrahydro-pyran-3-ol 
• 116454-05-8 (S)-1-((4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-phenylsulfanyl-5,6-dihydro-4H-pyran-2-yl)-propan-1-ol 

Relevant academic research and scientific papers

Functionally Substituted Vinyl Carbanions, 38. - C-Glucosides by Direct 1-C-Lithiation of 2-Phenylsulfinyl-Activated D-Glucal

Direct 1-C-lithiation of the readily available 2-phenylsulfinyl-D-glucals 6,h,l leads to reactive intermediates furnishing with aldehydes as electrophiles the compounds 7 in high yields.Subsequent removal of the phenylsulfinyl group with Raney nickel and

C-1 LITHIATION OF C-2 ACTIVATED GLUCALS

Direct lithiation of the readily available 2-benzyloxy and the 2-phenylthio glucals 1 and 7 at the anomeric carbon atom leads to intermediates reacting with different electrophiles.Subsequent removal of the phenylthio group in compounds 9a, b with Raney-nickel and distereospecific 1-hydrogen- and 2-hydroxy-transfer with the BH3*SMe2/H2O2, NaOH system provides a convenient entry into functionalized C-glucopyranosides.