165876-55-1

Upstream product

• 149099-13-8 (2S,5S)-5-([(1,1-dimethyl)ethyldiphenylsilyl]oxymethyl)tetrahydrofuran-2-carbonitrile 
• 313963-29-0 (S)-1-((tert-butyldiphenylsilyl)oxy)hex-5-en-2-ol 
• 106731-74-2 tert-butyl[(2S)-oxiran-2-ylmethoxy]diphenylsilane 
• 292069-13-7 (2S,5S)-2,5-di[(tert-butyldiphenylsilyl)oxymethyl]-2,5-dihydrofuran 
• 292069-07-9 (2S,5S)-2,5-di(trityloxymethyl)-2,5-dihydrofuran 
• 292069-09-1 (2S,5S)-2,5-di(hydroxymethyl)-2,5-dihydrofuran 
• 41107-82-8 2,5-anhydro-D-mannitol 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 292069-11-5 (2S,5S)-2-[(tert-butyldiphenylsilyl)oxymethyl]-5-hydroxymethyl-2,5-dihydrofuran 

Downstream Products

• 149099-14-9 (2S,5S)-5-<(tert-Butyldiphenylsiloxy)methyl>tetrahydrofuran-2-carboxaldehyde 
• 1384974-76-8 C₃₃H₄₄O₅Si 
• 1371603-72-3 tert-butyl(((2S,5S)-5-((R,Z)-6-((tert-butyldiphenylsilyl)oxy)-7-((4-methoxybenzyl) oxy)hept-1-en-3-yn-1-yl)tetrahydrofuran-2-yl)methoxy)diphenylsilane 
• 1371603-73-4 (R)-2-((tert-butyldiphenylsilyl)oxy)-7-((2R,5S)-5-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydrofuran-2-yl)heptan-1-ol 
• 1371603-74-5 tert-butyl(((2S,5R)-5-((R)-6-((tert-butyldiphenylsilyl)oxy)-7-iodoheptyl) tetrahydrofuran-2-yl)methoxy)diphenylsilane 
• 1371603-82-5 (S)-3-((R)-2-((tert-butyldiphenylsilyl)oxy)-7-((2R,5S)-5-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydrofuran-2-yl)heptyl)-5-methylfuran-2(5H)-one 
• 1371603-83-6 (S)-3-((R)-2-((tert-butyldiphenylsilyl)oxy)-7-((2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl)heptyl)-5-methylfuran-2(5H)-one 
• 292069-24-0 Chloro-methanesulfonic acid (R)-1-[(2S,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-undecyl ester 

Relevant academic research and scientific papers

Total synthesis of (-)-goniotrionin

A stereoselective total synthesis of the reported structure of goniotrionin (4) has been accomplished. The key steps involved the opening of a chiral epoxide, a highly diastereoselective Mukaiyama aerobic oxidative cyclization, a selective 1,2-syn Mukaiyama aldol reaction, and a Noyori reduction.

Stereoselective synthesis of the 3-hydroxytetrahydropyran part of mucocin, an antitumor agent, based on rearrangement-ring expansion reaction of a tetrahydrofuran derivative

The synthesis of the 2,6-disubstituted 2,3-trans-3- hydroxytetrahydropyran part of mucocin, a potent antitumor agent, was accomplished based on the zinc acetate-induced ring expansion reaction of a tetrahydrofuran having a choloromethanesulfonate on the C

Stereoselective Additions of Chiral, Functionalized Organozinc Reagents to Achiral and Chiral Aldehydes: a Matched-Mismatched Case in Organozinc Chemistry

The additions of the enantiomerically pure organozinc reagents 17 and 33 to the THF-aldehyde 1 in the presence of the monodentate Lewis acid boron trifluoride-ether give the nonchelation-controlled addition products 7 and 36, respectively (stereoselectivity 95:5, 86:14).These results provide a route to oligo(tetrahydrofuran)s with the relative stereochemistry trans-syn-cis.A stereodirecting effect of the chiral center in the organozinc reagent 17 is found, leading to simple diastereoselectivies in the reaction with achiral aldehydes and to a matched-mismatched case in the reaction with the chiral aldehyde 1. - Key Words: Addition, stereoselective, nonchelation-controlled / Reagent, organozinc / Stereodifferentiation, double / Oligo(tetrahydrofuran)