154912-69-3

Upstream product

• 96154-47-1 (R)-2-methyl-1,4-butanediol 4-benzyl ether 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 136786-35-1 (2S)-1-(tert-butyldiphenylsilyloxy)-2-methyl-3-(toluenesulfonyloxy)propane 
• 95514-04-8 (R)-3-(tert-butyldiphenylsilyloxy)-2-methylpropan-1-ol 
• 95514-03-7 (S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propionic acid methyl ester 
• 100-39-0 benzyl bromide 
• 154912-70-6 (3R)-4-{[tert-butyl(diphenyl)silyl]oxy}-3-methylbutan-1-ol 
• 186641-79-2 (R)-4-((tert-Butyldiphenylsilyl)oxy)-3-methylbutanal 
• 186641-76-9 (2R)-1-(tert-butyldiphenylsilyloxy)-3-cyano-2-methylpropane 
• 154912-68-2 (2R,3R)-5-benzyloxy-3-methylpentane-1,2-diol 
• 91550-14-0 (2R)-4-(Benzyloxy)-2-methyl-1-butanal 
• 89923-31-9 (E)-5-(benzyloxy)pent-2-en-1-ol 
• 111466-55-8 ((2S,3S)-3-(2-(benzyloxy)ethyl)oxiran-2-yl)methanol 

Downstream Products

• 96154-47-1 (R)-2-methyl-1,4-butanediol 4-benzyl ether 
• 1443232-98-1 5-[(2R)-4-benzoxy-2-methylbutylsulfanyl]-1-phenyl-1H-tetrazole 
• 1443232-99-2 5-[(2R)-4-benzyloxy-2-methylbutane-1-sulfonyl]-1-phenyl-1H-tetrazole 
• 1443233-00-8 8-benzoxy-1-(tert-butyldiphenylsilyloxy)-(2R,6R)-2,6-dimethyl-4-(E)-4-octene 
• 1443233-36-0 8-benzoxy-1-(tert-butyldiphenylsilyloxy)-(2R,6R)-2,6-dimethyl-4-(Z)-4-octene 
• 154912-74-0 (R)-2-Benzyloxy-1-{(2R,3S)-3-[(R)-4-(tert-butyl-diphenyl-silanyloxy)-3-methyl-butyl]-oxiranyl}-ethanol 
• 154912-80-8 (S)-1-[(R)-6-((4S,6S)-6-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-4-methyl-2,3-dioxo-hexanoyl]-piperidine-2-carboxylic acid methyl ester 
• 1054618-19-7 (S)-1-[(R)-6-((4S,6S)-6-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-3-hydroxy-4-methyl-hexanoyl]-piperidine-2-carboxylic acid methyl ester 
• 154912-75-1 (2S,4S,7R)-1-Benzyloxy-8-(tert-butyl-diphenyl-silanyloxy)-7-methyl-octane-2,4-diol 
• 154912-73-9 (Z)-(2S,7R)-1-Benzyloxy-8-(tert-butyl-diphenyl-silanyloxy)-7-methyl-oct-3-en-2-ol 
• 154912-72-8 (2S,7R)-1-Benzyloxy-8-(tert-butyl-diphenyl-silanyloxy)-7-methyl-oct-3-yn-2-ol 
• 154912-71-7 Methanesulfonic acid (R)-4-(tert-butyl-diphenyl-silanyloxy)-3-methyl-butyl ester 
• 154912-67-1 ((R)-4-Bromo-2-methyl-butoxy)-tert-butyl-diphenyl-silane 
• 154912-78-4 (R)-4-((4S,6S)-6-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-2-methyl-butyraldehyde 

Relevant academic research and scientific papers

Highly stereocontrolled total synthesis of β-d-mannosyl phosphomycoketide: A natural product from mycobacterium tuberculosis

β-d-Mannosyl phosphomycoketide (C32-MPM), a naturally occurring glycolipid found in the cell walls of Mycobacterium tuberculosis, acts as a potent antigen to activate T-cells upon presentation by CD1c protein. The lipid portion of C32-MPM contains a C32-mycoketide, consisting of a saturated oligoisoprenoid chain with five chiral methyl branches. Here we develop several stereocontrolled approaches to assemble the oligoisoprenoid chain with high stereopurity (>96%) using Julia-Kocienski olefinations followed by diimide reduction. By careful choice of olefination sites, we could derive all chirality from a single commercial compound, methyl (2S)-3-hydroxy-2-methylpropionate (>99% ee). Our approach is the first highly stereocontrolled method to prepare C32-MPM molecule with >96% stereopurity from a single >99% ee starting material. We anticipate that our methods will facilitate the highly stereocontrolled synthesis of a variety of other natural products containing chiral oligoisoprenoid-like chains, including vitamins, phytol, insect pheromones, and archaeal lipids.

Studies directed towards the synthesis of rapamycin: Stereoselective synthesis of C-1 to C-15 segment

Stereoselective synthesis of a suitably functionalized C-1 to C-15 segment of rapamycin is described.