123765-20-8

Upstream product

• 1738-80-3 L-serine benzyl ester p-toluenesulfonate hydrochoride 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 60022-62-0 L-serine benzyl ester hydrochloride 
• 879278-55-4 (S)-benzyl 2-amino-3-hydroxypropanoate hydrochloride 

Downstream Products

• 1219447-43-4 C₂₀H₂₈N₂O₃SSi 
• 1353654-61-1 (S)-4-(benzyloxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)-1H-pyrrol-2(5H)-one 
• 267876-90-4 Fmoc-Ala-Pro-D-Phe-Ser(TBS)-Thr(rprenyl)-Ser(rprenyl)-Ile-OMe 
• 267877-03-2 C₅₀H₈₃N₇O₁₁Si 
• 267877-04-3 2-[2-[2-[2-(2-{[1-(2-amino-propionyl)-pyrrolidine-2-carbonyl]-amino}-3-phenyl-propionylamino)-3-(tert-butyl-dimethyl-silanyloxy)-propionylamino]-3-(1,1-dimethyl-allyloxy)-butyrylamino]-3-(1,1-dimethyl-allyloxy)-propionylamino]-3-methyl-pentanoic acid 

Relevant academic research and scientific papers

Synthesis and Evaluation of Cyclic Acetals of Serine Hydroxylamine for Amide-Forming KAHA Ligations

The α-ketoacid-hydroxylamine (KAHA) ligation allows the coupling of unprotected peptide segments. The most widely used variant employs a 5-membered cyclic hydroxylamine that forms a homoserine ester as the primary ligation product. While very effective, m

NEW DIFLUOROKETAMIDE DERIVATIVES AS HTRA1 INHIBITORS

The invention provides novel compounds having the general formula (I) wherein wherein R1, R2, R3, R4, R5, R6, R7, R3, R8, R9, R10, R11, R12 and R23 are as described herein, compositions including the compounds and methods of using the compounds.

Gram-scale synthesis of iejimalide B

IejimalideB (2) is the most promising member of a small family of marine polyene macrolides endowed with remarkably selective activity against human cancer cell lines. As this product, however, is hardly available from the natural sources, a detailed evaluation requires the development of an efficient and practical synthetic approach. This challenge has now been met by adapting the first total synthesis of 2 previously reported by our group to the needs of high material throughput. Redesigning the access routes to the five required building blocks in combination with a careful optimization of the fragment coupling processes provided gram amounts of this valuable compound in a sequence of no more than 16 linear steps with an overall yield of about 7 %. Key elements of the successful strategy include: i) three hydrostannylation processes of elaborate terminal alkynes with "lower order" stannyl cuprates, ii) a Brown allylation, a Noyori transfer hydrogenation, and a Marshall propargylation to set the chiral centers at C9, C17, C22 and C23, and iii) a modified Takai-Utimoto olefination for the preparation of the very labile skipped 1,4-diene flanking the ester group. The assembly process benefited from a particularly mild protocol for the Stille cross-coupling previously developed in this laboratory, which clearly outperformed the alternative Suzuki reaction in terms of yield and scalability. The 24-membered macrocyclic frame was forged by a remarkably selective ring-closing metathesis reaction (RCM), in which two out of the ten double bonds present in the cyclization precursor were selectively activated with the aid of a second-generation Grubbs catalyst. Copyright

ANTI-INFECTIVE PYRROLIDINE DERIVATIVES AND ANALOGS

The present invention discloses compounds of Formula (I), or pharmaceutically acceptable salts, esters, or prodrugs thereof: which inhibit RNA-containing virus, particularly the hepatitis C virus (HCV). Consequently, the compounds of the present invention

Fluorescence-based detection of single nucleotide permutation in DNA via catalytically templated reaction

Templated reduction of low fluorescence azidocoumarin-PNA conjugate to high fluorescence aminocoumarin was achieved using a catalytic amount of DNA with single nucleotide resolution. The Royal Society of Chemistry.

A tuneable method for N-debenzylation of benzylamino alcohols

(Chemical Equation Presented) N-lodosuccinmide provides a mild, convenient, and tuneable reagent for the selective mono- or didebenzylation in representative, multifunctionalized carbohydrate and amino acid derived N-dibenzylamines with neighboring O-func

Total synthesis and revision of stereochemistry of the marine metabolite trunkamide A

The isolation of the cytotoxic Lissoclinum sp. metabolite trunkamide A was reported in 1996. After completion of a total synthesis in 1999, it became clear that the structure of this marine natural product had to be revised. We now report the first preparation of actual trunkamide A in a total synthesis that serves as an unambiguous structural and stereochemical proof. Highlights of our synthetic strategy are a Lewis acid assisted aziridine opening that was used for the preparation of the novel reverse- prenylated serine and threonine side chains as well as an efficient oxazoline-thiazoline interconversion on the macrocyclic skeleton. In addition, several stereoisomers prepared by complementary synthetic protocols serve to illustrate the general scope of our methodology and confirm the configurational assignment.