65276-91-7

Upstream product

• 96965-31-0 tert-butyl-4-(acetoxymethyl)-3-nitrobenzoate 
• 96965-30-9 4-(acetoxymethyl)-3-nitrobenzoic acid 
• 55715-03-2 4-bromomethyl-3-nitrobenzoic acid 
• 6232-88-8 4-bromomethylbenzoic Acid 
• 65276-90-6 2-nitro-4-(tert-butoxycarbonyl)benzyl bromide 
• 99-94-5 p-Toluic acid 

Downstream Products

• 65276-93-9 3-Formamido-4-hydroxymethylbenzoesaeure-t-butylester 
• 96965-29-6 Dts-Phe-ONb-tBu 
• 96965-27-4 Dts-Val-ONb-O-t-Bu 
• 96965-28-5 Dts-Leu-ONb-O-t-Bu 
• 96965-24-1 Dts-Val-ONb 
• 96965-25-2 Dts-Leu-ONb 
• 96965-26-3 Dts-Phe-ONb 
• 65276-94-0 4-chloromethyl-3-formylamino-benzoic acid tert-butyl ester 

Relevant academic research and scientific papers

Combinatorial dihydrobenzopyran library

Combinatorial libraries are disclosed which are represented by Formula I: wherein: S is a solid support; T'--L-- is an identifier residue; and --L'--II' is a ligand/linker residue. These libraries contain dihydrobenzopyrans of the formula: STR1 which interact (i.e., as agonists or antagonists) with α adrenergic receptors, dopamine receptors, ?-opiate receptors, and K+ channels and are inhibitors of carbonic anhydrase isozymes. They are useful in the treatment of ocular diseases such as glaucoma.

PROCESS FOR PREPARING INTERMEDIATES FOR A COMBINATORIAL DIHYDROBENZOPYRAN LIBRARY

Combinatorial libraries are disclosed which are represented by Formula I:(T'-L) q-S-C(O)-L'-II' I wherein:S is a solid support; T'-L-is an identifier residue; and-L'-II' is a ligand/linker residue. These libraries contain dihydrobenzopy

A Three-Dimensional Orthogonal Protection Scheme for Solid-Phase Peptide Synthesis under Mild Conditions

Several Nα-dithiasuccinoyl (Dts) amino acids (1) were esterified, by use of N,N'-dicyclohexylcarbodiimide (DCC) and without racemization, to tert-butyl 4-(hydroxymethyl)-3-nitrobenzoate (8).The resultant handle derivatives 4 were treated with trifluoroacetic acid to yield crystalline 4-(Nα-Dts-aminoacyloxymethyl)-3-nitrobenzoic acids (3), which were quantitatively incorporated onto aminomethylcopoly(styrene-1percent divinylbenzene)-resins by DCC-mediated couplings to give the starting point for stepwise solid-phase synthesis of peptides anchored as o-nitrobenzyl (ONb) esters.Assembly of the protected leucine-enkephalin-resin derivative Dts-Tyr(t-Bu)-Gly-Gly-Phe-Leu-ONb-resin (2) was achieved from the appropiate Dts-amino acids by a highly efficient protocol.By carrying out, in each conceivable order, either in solution or on the solid phase, one two, or all three of the following orthogonal treatments , the common resin-bound intermediate 2 became the source of four partially or fully deblocked leucine-enkephalin derivatives.These four, namely Dts-Tyr(t-Bu)-Gly-Gly-Phe-Leu-OH, Dts-Tyr-Gly-Gly-Phe-Leu-OH, H-Tyr(t-Bu)-Gly-Gly-Phe-Leu-OH, and H-Tyr-Gly-Gly-Phe-Leu-OH, were each obtained pure in good yields and were characterized by amino acid composition, HPLC, 300-MHz 1H NMR, and fast atom bombardment mass spectrometry.The protected dipeptidyl sequence Prot-D-Val-L-Pro-ONb-resin was assembled with three different Nα-amino protecting groups and exposed to the recommended deblocking reagents.Loss of chains from the resin by diketopiperazine formation was very rapid with Prot=9-fluorenylmethoxycarbonyl (Fmoc) and also substantial with Prot=tert-butoxycarbonyl (Boc), but rather negligible wit h Prot=Dts.Thus, these experiments demonstrate the feasibility and benefits of a mild three-dimensional orthogonal protection scheme based on Dts for Nα-amino protection, tert-butyl derivatives for side chains, and o-nitrobenzyl esters for anchoring.