877833-53-9

Upstream product

• 22742-89-8 2-methyl-2,3-butadiene-1-ol 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 403805-83-4 methyl 4-(tert-butyldiphenylsilyloxy)-2-butynoate 

Downstream Products

• 877833-52-8 (E)-4-{(2S,4S,5S,6R)-6-[(Z)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-propenyl]-5-methyl-4-triethylsilanyloxy-tetrahydro-pyran-2-yl}-but-2-enal 
• 877833-51-7 (2R,3S,4S,6S)-6-Allyl-2-[(Z)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propenyl]-3-methyl-4-triethylsilanyloxy-tetrahydro-pyran 
• 877833-43-7 (S)-4-Benzyl-3-[(Z)-(2S,3R)-6-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-2,5-dimethyl-hex-4-enoyl]-oxazolidin-2-one 
• 877833-46-0 bromo-acetic acid 1-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-4-(tert-butyl-diphenyl-silanyloxy)-3-methyl-but-2-enyl ester 
• 877833-50-6 (4S,5R,6R)-2-Allyl-6-[(Z)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propenyl]-5-methyl-tetrahydro-pyran-2,4-diol 
• 877833-45-9 1-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-2,5-dimethyl-hex-4-en-3-ol 
• 877833-47-1 Bromo-acetic acid (Z)-(R)-4-(tert-butyl-diphenyl-silanyloxy)-1-((R)-2-hydroxy-1-methyl-ethyl)-3-methyl-but-2-enyl ester 
• 877833-48-2 Bromo-acetic acid (Z)-(R)-4-(tert-butyl-diphenyl-silanyloxy)-3-methyl-1-((S)-1-methyl-2-oxo-ethyl)-but-2-enyl ester 
• 877833-44-8 (Z)-(2R,3R)-6-(tert-Butyl-diphenyl-silanyloxy)-2,5-dimethyl-hex-4-ene-1,3-diol 
• 877833-42-6 4-(tert-butyl-diphenyl-silanyloxy)-3-methyl-but-2-enal 

Relevant academic research and scientific papers

Stereodivergent Hydroboration of Allenes

Full details of a stereodivergent hydroboration of allenes are reported. While hydroboration of an allene with 9-BBN provided a thermodynamically stable (E)-allylic alcohol after oxidative work-up, the reaction of an identical allene with HB(Sia)2 (disiamylborane) formed a (Z)-allylic alcohol as the kinetic product. The developed conditions allowed for the synthesis of trisubstituted olefins in a highly stereoselective fashion, which is known to be challenging. The method was also applied to the stereodivergent synthesis of structural motifs such as skipped dienes and allylbenzenes, which are often embedded in biologically active natural products.

An efficient synthesis of the C1-C14 subunit of (-)-lasonolide A via a target oriented β-C-glycoside formation sequence

An efficient synthesis of the C1-C14 subunit resident in (-)-lasonolide A is reported herein. The key reaction features that were utilized include a Molander-Reformatsky SmI2 mediated intramolecular aldol reaction followed