66967-01-9Relevant articles and documents
Strict reagent control in the asymmetric allylboration of N-TIPS-α-amino aldehydes with the B-allyl-10-TMS-9-borabicyclo[3.3.2] decanes
Soto-Cairoli, Buddy,Soderquist, John A.
supporting information; experimental part, p. 401 - 404 (2009/07/04)
(Chemical Equation Presented) The allylboration of enantiomerically pure N-triisopropylsilyl-α-amino aldehydes (2) with B-allyl-10-trimethylsilyl- 9-borabicyclo[3.3.2]decanes (1) proceeds cleanly at -78 °C, exhibiting essentially complete reagent control. After an oxidative workup, an HOAc-mediated N→O TIPS rearrangement facilitates the clean formation of stable O-TIPS protected β-amino alcohol derivatives 3 which are isolated in 60-83% yields in >96% de and >99% ee. For the leucinal series (R = i-Bu), an efficient entry to either statine (8aSS) or epi-statine (8aRS) is reported illustrating the versatility of this potent 1/2 combination.
An affinity-based probe for the proteomic profiling of aspartic proteases
Chattopadhaya, Souvik,Chan, Elaine W. S.,Yao, Shao Q.
, p. 4053 - 4056 (2007/10/03)
We have developed an affinity-based probe for the proteomic profiling of aspartic proteases. Our probe was shown to be selective towards aspartic proteases over other proteins. It was also shown that the strategy may be used to label selectively aspartic proteases in the presence of a large excess of other proteins, thus making it useful for future proteome profiling experiments.
A synthetic approach to 3-hydroxy 4-substituted carboxylic acids based on the stereoselective reduction of 1-trimethylsilyl-1-alkyn-3-ones
Alemany, Carme,Bach, Jordi,Garcia, Jordi,López, Marta,Rodríguez, Ana B.
, p. 9305 - 9312 (2007/10/03)
The oxazaborolidine-mediated reduction of chiral, 4-substituted 1-trimethylsilyl-1-alkyn-3-ones followed by hydroboration affords syn or anti 3-hydroxy 4-substituted carboxylic acids, common substructures of a number of biologically active macrolides, peptides and depsipeptides, with high control on the new C(3) stereocenter. This strategy has been applied to the synthesis of (3S,4S)-3-hydroxy-4-methylheptanoic acid and of N-Boc-statine, constituents of permentin A and pepstatin, respectively. (C) 2000 Elsevier Science Ltd.