950746-99-3

Upstream product

• 950746-98-2 6-[(4-methoxybenzyl)oxy]-1-trimethylsilyl-1-hexyn-3-one 
• 108-05-4 vinyl acetate 
• 957300-51-5 (±)-6-(4-methoxybenzyloxy)-1-(trimethylsilyl)hex-1-yn-3-ol 
• 1066-54-2 trimethylsilylacetylene 
• 119649-27-3 4-((4-methoxybenzyl)oxy)butanal 

Downstream Products

• 950747-16-7 (S)-6-((4-methoxybenzyl)oxy)hex-1-yn-3-ol 
• 950747-02-1 (S)-3-[(tert-butyldimethylsilyl)oxy]-6-[(4-methoxybenzyl)oxy]-1-hexyne 
• 950747-12-3 C₂₂H₄₃O₄Si₂SeC₆H₅ 
• 950747-03-2 (1E,3S)-3-[(tert-butyldimethylsilyl)oxy]-1-iodo-6-[(4-methoxybenzyl)oxy]-1-hexene 

Relevant academic research and scientific papers

Asymmetric total synthesis of (-)-mangiferaelactone by using an appropriately substituted thiophene as a masked synthon for C-alkyl glycoside

Abstract Asymmetric total synthesis of naturally occurring nonenolide (-)-mangiferaelactone was attempted through RCAM (ring closing alkyne metathesis) reaction. As the attempted RCAM reaction failed, the synthesis was finally achieved by successful explo

Synthesis of (S)-imperanene by using allylic substitution

(Chemical Equation Presented) Synthesis of (S)-imperanene (1) was studied by using copper-assisted allylic substitution of ArCH=CHCH(L)CH2Ar (L: leaving group) and (i-PrO)Me2SiCH2MgCl. Preliminary substitution between PhCH=CHCH(L)Me (L = AcO, PivO, MeOCO2, (2-Py)CO2) and Bu copper reagents derived from BuMgX (X = Br, Cl) and CuBr·Me2S or CuCl in 1:1-40:1 ratios suggested acetate 28 as the best substrate. To prepare 28, kinetic resolution of racemic (E)-TMSCH=CHCH(OH)CH2Ar2 (Ar2 = (p-TBSO)(m-MeO)C6H3) carried out by using the asymmetric epoxidation with (-)-DIPT afforded the corresponding epoxy alcohol and (S)-allylic alcohol. After separation by chromatography, these products were converted to (S,E)-Bu3SnCH=CHCH(OH)CH2Ar2, which upon palladium-catalyzed coupling with Ar2-I followed by acetylation gave 28 (95-98% ee). Substitution of 28 with (i-PrO)Me 2SiCH2MgCl and CuBr·Me2S in a 4:1 ratio at 0°C proceeded cleanly to produce 29 with 100% inversion in 92% yield. Finally, Tamao oxidation furnished 1.

First total synthesis of modiolide A, based on the whole-cell yeast-catalyzed asymmetric reduction of a propargyl ketone

While the first total synthesis of modiolide A (1a), a 10-membered ring lactone with a marine-origin was achieved, an important chiral building block for constructing the chirality at C-4 in 1a, (S)-6-[(4-methoxybenzyl)oxy]-1-trimethylsilyl-1-hexyn-3-ol (