296268-44-5

Upstream product

• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 136883-91-5 (2R,3S,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran-5-carbaldehyde 

Downstream Products

• 1354577-26-6 3,4-bis(benzyloxy)-2-benzyloxymethyl-5-ethyl-3,4-dihydro-2H-pyran 
• 871695-89-5 (2R,3R,4S,4aR,5R,7S,8R,8aR)-3,4-Bis-benzyloxy-2-benzyloxymethyl-8-tert-butoxycarbonylamino-4a,5-dihydroxy-octahydro-chromene-7-carboxylic acid ethyl ester 
• 871695-85-1 (2R,3S,4R,7S,8R,8aS)-3,4-Bis-benzyloxy-2-benzyloxymethyl-8-tert-butoxycarbonylamino-3,4,6,7,8,8a-hexahydro-2H-chromene-7-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Ni-Catalyzed Cross-Coupling of 2-Iodoglycals and 2-Iodoribals with Grignard Reagents: A Route to 2-C-Glycosides and 2’-C-Nucleosides

The synthesis of 2-C-glycals and 2-C-ribals was achieved in good yields using a nickel-catalyzed cross-coupling between 2-iodoglycals and 2-iodoribal respectively and Grignard reagents. The prepared 2-C-glycals and ribals were then transformed into 2-C-2-deoxyglycosides, 2-C-diglycosides and 2’-C-2’-deoxynucleosides. The developed method was applied to the synthesis of a 2-chloroadenine. 2’-deoxyribonucleoside – a structural analogue of cladribine (Mavenclad, Leustatin) and clofarabine (Clolar, Evoltra), two compounds used in the treatment of relapsing-remitting multiple sclerosis and hairy cell leukemia.

Glycosidation of 3,4,6-tri-o-benzyl-2-ethenyl-D-glucal - A route to 2-C-(β-methyl)methylene glycosides

Monosaccharidic and disaccharidic 2-C-(β-methyl)methylene glycosides were synthesized by an electrophilic conjugate addition reaction of ROH-type compounds in the presence of Ph3+PH Br- to 2-ethenyl-3,4,6-tri-O-benzyl-D-glucal 1, functioning as a model glycosyl donor. This 2-vinyl glucal derivative represents a series of 2-vinyl and 2-butadienyl glycals, prepared by Wittig-type methylenation of pyranosidic conjugated enals, derived from glucal, galactal and lactal. The exo-(β-methyl)methylene group paves the way for further chemical transformations.