474333-63-6

Upstream product

• 18292-38-1 2-methallyltrimethylsilane 
• 2186-92-7 p-Anisaldehyde dimethyl acetal 
• 3876-46-8 (2R,3S)-2,4-dimethyl-1,3-pentane diol 
• 3876-47-9 (2R*,3S*)-2,4-dimethyl-1,3-pentanediol 
• 63584-47-4 (1-tert-butylsulfanyl-vinyloxy)trimethylsilane 
• 31469-16-6 1-ethoxy-1-((trimethylsilyl)oxy)-2-methylpropene 
• 123-11-5 4-methoxy-benzaldehyde 
• 67883-62-9 2-methylallyltributyltin 

Downstream Products

• 1380244-48-3 (2R,3S)-3-(4-methoxybenzyloxy)-2,4-dimethylpentan-1-ol 
• 1380244-49-4 (2R,4S,5S,6R,7S)-5-hydroxy-7-(4-methoxybenzyloxy)-4,6,8-trimethyl-3-oxononan-2-yl benzoate 
• 1380244-59-6 (2R,4S)-4-((4S,5S,6S)-6-isopropyl-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-3-oxopentan-2-yl benzoate 
• 1380244-50-7 (2R,4S,5S,6S,7S)-7-((4-methoxybenzyl)oxy)-4,6,8-trimethyl-3-oxo-5-((triethylsilyl)oxy)nonan-2-yl benzoate 
• 1380244-51-8 (4S,5S,6S,7S)-7-((4-methoxybenzyl)oxy)-4,6,8-trimethyl-5-((triethylsilyl)oxy)nonan-3-one 
• 1380244-52-9 (2S,3S,4R,6S,7S,8S,9S)-2-((2S,4S,5R,6S)-6-ethyl-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-3-hydroxy-9-((4-methoxybenzyl)oxy)-4,6,8,10-tetramethyl-7-((triethylsilyl)oxy)undecan-5-one 
• 1380244-53-0 (2R,4R,6S,7S,8S,9S)-2-((2S,4R,5R,6S)-6-ethyl-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-9-((4-methoxybenzyl)oxy)-4,6,8,10-tetramethyl-7-((triethylsilyl)oxy)undecane-3,5-dione 
• 1380244-54-1 (R)-(3S,4S,5S,6S)-3-((4-methoxybenzyl)oxy)-2,4,6-trimethyl-7-oxononan-5-yl 2-((2S,4R,5R,6S)-6-ethyl-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)propanoate 
• 1380244-55-2 (2R,3R,4R,5S)-(3S,4S,5S,6S)-3-((4-methoxybenzyl)oxy)-2,4,6-trimethyl-7-oxononan-5-yl 3,5-dihydroxy-2,4-dimethylheptanoate 
• 1380244-56-3 (2R,3R,4S)-(3S,4S,5S,6S)-3-((4-methoxybenzyl)oxy)-2,4,6-trimethyl-7-oxononan-5-yl 3-hydroxy-2,4-dimethyl-5-oxoheptanoate 

Relevant academic research and scientific papers

In silico inspired total synthesis of (-)-dolabriferol

Going retro: The diazabicycloundecane-induced retro-Claisen rearrangement of a linear precursor serves as the key step to form the hindered ester of the polypropionate dolabriferol (1, see scheme, PMB=p-methoxybenzyl, PMP=p-methoxyphenyl, TES=triethylsilyl). The rearrangement is thought to mimic the biosynthetic formation of 1. Copyright

Inter- and intramolecular differentiation of enantiotopic dioxane acetals through oxazaborolidinone-mediated enantioselective ring-cleavage reaction: Kinetic resolution of racemic 1,3-alkanediols and asymmetric desymmetrization of meso-1,3-polyols

Acetals derived from racemic 1,3-alkanediols undergo kinetic resolution in chiral oxazaborolidinonemediated ring-cleavage reaction with nucleophiles such as enol silanes and allylic silanes. Enantioselectivity of the reaction is affected by nucleophiles, the N-sulfonyl groups of oxazaborolidinones, and the substituents attached to the acetal carbon. For disubstituted acetals rac-1 and for trisubstituted acetal rac-2, derived from syn-2,4-dimethyl-1,3-pentanediol, satisfactory enantioselectivity is obtained by using methallylsilane 7b,c as a nucleophile in combination with N-mesyloxazaborolidinone 4a. On the other hand, enantioselective reaction of trisubstituted acetal rac-3b, derived from anti-2,4-dimethyl-1,3-pentanediol, is realized by using silyl ketene acetal 5e in combination with N-tosyloxazaborolidinone 4b. The reaction conditions optimized for the kinetic resolution, or enantiomer differentiating reaction, of the racemic acetals are successfully applied to asymmetric desymmetrization of meso-1,3-polyols through intramolecular differentiation of the enantiotopic acetal moieties of the bis-acetal derivatives. The utility of the ring-cleavage reaction as a method for enantioselective terminal differentiation of prochiral polyols is demonstrated in convergent asymmetric synthesis of pentol derivative 35 corresponding to the C(19)-C(27) ansachain of rifamycin S.