105544-96-5

Upstream product

• 105544-90-9 7-O-(t-butyldiphenylsilyl)-1,2-dideoxy-5,6-O-isopropylidene-4-C-methyl-keto-D-arabino-3-heptulose 
• 100-39-0 benzyl bromide 
• 116776-80-8 (E)-(2S,3R,4R,7R)-3-(tert-Butyl-dimethyl-silanyloxy)-7-hydroxy-2,4,6-trimethyl-non-5-enoic acid methyl ester 
• 116776-79-5 (E)-(2S,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-7-oxo-non-5-enoic acid methyl ester 
• 116776-77-3 (2S,3S,4S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-7-oxo-5-phenylsulfanyl-nonanoic acid methyl ester 
• 124928-76-3 (2R,3R)-3-Benzyloxy-2-((4R,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-pentan-2-ol 
• 105544-89-6 3-O-benzyl-7-O-(t-butyldiphenylsilyl)-1,2-dideoxy-5,6-O-isopropylidene-4-C-methyl-D-manno-heptitol 
• 105544-88-5 (R)-2-[(4R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-pentane-2,3-diol 
• 124928-77-4 (2R,3R,4S,5R)-5-Benzyloxy-4-methyl-heptane-1,2,3,4-tetraol 

Downstream Products

• 124928-78-5 (R)-3-benzyloxy-2-methyl-2-pentanol 

Relevant academic research and scientific papers

Kinetic resolution of racemic allylic alcoholsviairidium-catalyzed asymmetric hydrogenation: scope, synthetic applications and insight into the origin of selectivity

Asymmetric hydrogenation is one of the most commonly used tools in organic synthesis, whereas, kinetic resolutionviaasymmetric hydrogenation is less developed. Herein, we describe the first iridium catalyzed kinetic resolution of a wide range of trisubstituted secondary and tertiary allylic alcohols. Large selectivity factors were observed in most cases (sup to 211), providing the unreacted starting materials in good yield with high levels of enantiopurity (ee up to >99%). The utility of this method is highlighted in the enantioselective formal synthesis of some bioactive natural products including pumiliotoxin A, inthomycin A and B. DFT studies and a selectivity model concerning the origin of selectivity are presented.

SYNTHETIC STUDIES OF ERYTHROMYCINS. II. ENANTIOSPECIFIC SYNTHESIS OF A C-10-C-13 SEGMENT OF ERYTHRONOLIDE A FROM D-RIBOSE

(3R,4R,5R)-5-O-Benzyl-2-iodo-3,4-O-isopropylidene-4-methyl-1-heptene-3,4,5-triol 3, a C-10-C-13 synthetic segment of erythronolide A (1) was enantiospecifically synthesized in sixteen steps and 8.3percent overall yield from D-ribose.