66967-01-9

Upstream product

• 67010-44-0 (3R,4S)-(t-butyloxycarbonyl)-4-amino-3-hydroxy-6-methylheptanoic acid ethyl ester 
• 58521-45-2 tert-butoxycarbonyl-L-leucinal 
• 95061-51-1 (S)-2-acetoxy-1,1,2-triphenylethanol 
• 113283-88-8 (4S,5R)-3-(tert-butoxycarbonyl)-5-(carboxymethyl)-4-isobutyloxazolidin-2-one 
• 128013-71-8 (4S)-Boc-statine 1,1,2-triphenylethyl ester 
• 128013-71-8 (4S)-Boc-statine 1,1,2-triphenylethyl ester 
• 254752-33-5 C₁₉H₃₇NO₃Si 
• 87694-50-6 N-(tert-butoxycarbonyl)-L-leucine-N'-methoxy-N'-methylamide 
• 24424-99-5 di-tert-butyl dicarbonate 
• 113283-61-7 benzyl (S)-1-isobutyl-2,2-dimethoxyethylcarbamate 
• 936226-65-2 (2S,3R)-tert-butyl 3-hydroxy-2-isobutyl-5-oxopyrrolidine-1-carboxylate 
• 254752-25-5 C₁₉H₃₅NO₃Si 
• 537035-65-7 (4S,5R)-3-(tert-butoxycarbonyl)-5-carboxynmethyl-4-isobutyl-2,2-dimethyl-1,3-oxazolidine 
• 254752-31-3 (3R,4S)-4-(tert-butoxycarbonylamino)-6-methyl-1-trimethylsilylhept-1-yn-3-ol 

Downstream Products

• 114995-98-1 (3S,4S)-3-[(Benzyloxycarbonyl)amino]-4-[(tert-butoxycarbonyl)amino]-6-methyl-heptanoic acid dicyclohexylamine salt 
• 114995-97-0 (1S,2S)-<1-(4-oxo-2-azetidinyl)-3-methylbutyl>carbamic acid 1,1-dimethylethyl ester 
• 104021-83-2 methyl (3S,4S)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-6-methyl-3-<<(phenylmethoxy)carbonyl>amino>heptanoate 
• 100512-24-1 (3S,4S)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-6-methyl-3-<<(phenylmethoxy)carbonyl>amino>heptanoic acid 
• 109292-04-8 (4S,5S)-4-<<(phenylmethoxy)carbonyl>amino>-5-(2'-methylpropyl)-2-oxopyrrolidine 

Relevant academic research and scientific papers

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

(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

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.

Intramolecular nucleophilic epoxidation of γ-amino-α,β- unsaturated esters with an N-hydroperoxymethyl group

Intramolecular nucleophilic epoxidation reactions of γ-amino-α, β-unsaturated esters have been studied for the first time with a hydroperoxymethyl group attached to the nitrogen atom. The epoxidation was fast under mild basic conditions and highly anti se

A stereodivergent approach to syn- and anti-β-hydroxy-γ-amino acids. Enantioselective synthesis of N-Boc-statine and N-Boc-3-epistatine mediated by sulfoxides

Asymmetric syntheses of the syn- and anti-stereoisomers of N-Boc statine, based on the stereodivergent reduction of a single sulfoxide 5, derived from N-Boc-L-leucine, are reported.

A synthetic approach to 3-hydroxy 4-substituted carboxylic acids based on the stereoselective reduction of 1-trimethylsilyl-1-alkyn-3-ones

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.

A versatile approach to N-Boc-statine and N-Boc-norstatine based on the reduction of 1-trialkylsilyl acetylenic ketones. Strong remote effect of the C(1) substituent on the stereoselectivity

(formula presented) An efficient, unified approach to chiral, protected β-hydroxy γ-amino and α-hydroxy β-amino acids derived from Boc-L-leucine has been accomplished on the basis of the oxazaborolidine-controlled, stereoselective reduction of 1-trialkyls

Stereoselective vinylation of amino aldehydes using 2-trimethylsilylethylidentriphenylphosphorane

2-Trimethylsilylethylidentriphenylphosphorane reacts stereoselectively with α-amino aldehydes giving the Cram chelation controlled product of vinylation of the carbonyl group. The olefinic 1,2-amino alcohols obtained with this reaction are important inter

STEREOSELECTIVE SYNTHESIS OF (3R,4S)-N-BOC-STATINE

A stereoselective synthesis of (3R,4S)-N-BOC-Statine was achieved through an aldol condensation of N-BOC-L-Leucinal with a boron enolate of an appropriate chiral auxiliary described by Evans.

Asymmetric Synthesis of 2- Amino Alcohol Derivatives from (S)-α-Amino Aldehydes via Acetal Templates

Titanium tetrachloride mediated addition of allyltrimethylsilane to chiral acetals derived from (S)-α-amino aldehydes and (+)-(2S,4S)-pentane-2,4-diol gave the anti-2-amino alcohol derivatives with considerably high diastereoselectivity.On the other hand,