188409-88-3

Upstream product

• 137618-69-0 2-benzyloxy-3-((tert-butoxycarbonyl)amino)propanol 
• 100-39-0 benzyl bromide 
• 24424-99-5 di-tert-butyl dicarbonate 
• 143396-63-8 (R)-3-Amino-2-benzyloxy-propan-1-ol 

Downstream Products

• 188410-04-0 (E)-(S)-4-Benzyloxy-5-tert-butoxycarbonylamino-pent-2-enoic acid methyl ester 
• 188410-06-2 (E)-(S)-6-Benzyloxy-7-tert-butoxycarbonylamino-hept-2-enoic acid methyl ester 
• 188409-89-4 (S)-4-Benzyloxy-5-tert-butoxycarbonylamino-pentanoic acid methyl ester 
• 188409-92-9 ((E)-(S)-2-Benzyloxy-7-hydroxy-hept-5-enyl)-carbamic acid tert-butyl ester 
• 188410-05-1 ((S)-2-Benzyloxy-5-hydroxy-pentyl)-carbamic acid tert-butyl ester 
• 188409-91-8 (S)-5-Benzyloxy-2-hydroxy-piperidine-1-carboxylic acid tert-butyl ester 
• 188410-03-9 ((R)-2-Benzyloxy-3-oxo-propyl)-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

ANTITHROMBOTIC ETHERS

This application relates to a compound of formula I (or a prodrug thereof or a pharmaceutically acceptable salt of the compound or prodrug thereof) as defined herein, pharmaceutical compositions thereof, and its use as an inhibitor of factor Xa and/or thrombin, as well as a process for its preparation and intermediates therefor (I).

Recognition of the minor groove of DNA by hairpin polyamides containing α-substituted-β-amino acids

Incorporation of the flexible amino acid β-alanine (β) into hairpin polyamides composed of N-methylpyrrole (Py) and N-methylimidazole (Im) amino acids is required for binding to DNA sequences longer than seven base pairs with high affinity and sequence selectivity. Pairing the α-substituted-β- amino acids (S)-isoserine ((S)Is), (R)-isoserine ((R)Is), β-aminoalanine (Aa), and α-fluoro-β-alanine (Fb) side-by-side with β in hairpin polyamides alters DNA binding affinity and selectivity relative to the parent polyamide containing a β/β pairing. Quantitative DNase I footprinting titration studies on a restriction fragment containing the sequences 5'- TGCNGTA-3' (N = A, T, G, and C) show that the polyamide ImPy(S)IsImPy-γ- PyPyβImPy-β-Dp (S)Is/β pairing) binds to N = T (K(a) = 4.5 x 109 M-1) in preference to N = A (K(a) = 6.2 x 108 M-1). This result stands in contrast to the essentially degenerate binding of the parent ImPyβImPy-γ- PyPyβImPy-β-Dp (β/β pairing) to N = T and N = A, and to the slight preference of ImPyβImPy-γ-PyPy(S)IsImPy-β-Dp (β/(S)Is pairing) to N = A over N = T. Additionally, this study reveals that incorporation of (R)Is, Aa, and Fb into polyamides significantly reduces binding affinity. Therefore, DNA binding in the minor groove is sensitive to the stereochemistry, steric bulk, and electronics of the substituent at the α-position of β-amino acids in hairpin polyamides containing β/β pairs.

1,4-asymmetric induction in palladium(II)-catalyzed intramolecular N-alkylation reaction. Construction of 2-functionalized 5-hydroxypiperidine

Palladium(II)-catalyzed cyclization of optically active urethanes containing an allylic alcohol moiety was examined. Efficient 1,4-asymmetric induction was found in this reaction. The cycloadducts were converted to pseudoconhydrine.