108149-61-7

Upstream product

• 72-19-5 L-threonine 
• 60538-19-4 N-(tert-butoxycarbonyl)-l-threonine methyl ester 
• 77-76-9 2,2-dimethoxy-propane 
• 2592-18-9 N-(t-Butyloxycarbonyl)-L-threonine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 116-11-0 2-Methoxypropene 

Downstream Products

• 108149-62-8 (4S,5R)-3-(tert-Butoxycarbonyl)-4-formyl-2,2,5-trimethyloxazolidine 

Relevant academic research and scientific papers

A new access to enantiomerically pure deoxy aminohexoses: Methyl 4-amino-4,6-dideoxy gulopyranoside and epi-tolyposamine

New efficient synthetic routes have been developed starting from the fully protected L-threonine derivative 1 for some deoxy-4-aminohexoses: methyl 4-amino-4,6-dideoxy gulopyranoside 2 and epi-tolyposamine 3. The title compounds were synthesized using an improved Horner-Emmons reaction of the threonine derived aldehyde 7. A new method for selective removal of the aminal protection is also reported.

THAILANSTATIN ANALOGS

The invention provides novel cytotoxic compounds and cytotoxic conjugates comprising these cytotoxic compounds and cell-binding agents. More specifically, this invention relates to novel thailanstatin A analogs, useful as cytotoxic small molecule toxins i

CYCLIZED SULFAMOYLARYLAMIDE DERIVATIVES AND THE USE THEREOF AS MEDICAMENTS FOR THE TREATMENT OF HEPATITIS B

Inhibitors of HBV replication of Formula (I-A), including stereochemically isomeric forms, and salts, hydrates, solvates thereof, wherein Ra to Rd, and R1 to R8 have the meaning as defined herein. The present invention also relates to processes for preparing said compounds, pharmaceutical compositions containing them and their use, alone or in combination with other HBV inhibitors, in HBV therapy.

Synthesis of the N-(tert-butyloxycarbonyl)-O-triisopropylsilyl-d- pyrrolosamine glycal of lomaiviticins A and B via epimerization of l-Threonine

An efficient synthesis of the N-(tert-butyloxycarbonyl)-O- triisopropylsilyl-d-pyrrolosamine glycal of lomaiviticin A (1) and lomaiviticin B (2) is described. The synthesis is highlighted by the epimerization of the l-threonine-derived oxazolidine 10 to oxazolidine 11. This key epimerization reaction, which serves to establish the correct relative configuration of the carbohydrate unit, was made possible only after conformational analysis indicated that substituted oxazolidines may adopt conformations that preclude enolization.

FR901464 AND ANALOGS WITH ANTITUMOR ACTIVITY AND METHOD FOR THEIR PREPARATION

The present invention provides analogs of FR901464, as well as a methodology for preparing FR901464 and its analogs. These compounds display an anti-cancer activity and are candidates for therapies against a number of disease states associated with dysfunctional RNA splicing.

SYNTHESIS OF FR901464 AND ANALOGS WITH ANTITUMOR ACTIVITY

The present invention provides novel analogs of FR901464, as well as an improved methodology for preparing FR901464 and its analogs. These compounds display an anti-cancer activity and are candidates for therapies against a number of disease states associ

An improved method for culturing Streptomyces sahachiroi: Biosynthetic origin of the enol fragment of azinomycin B

Azinomycin B is an environmental DNA crosslinking agent produced by the soil microorganism Streptomyces sahachiroi. While the agent displays potent cytotoxic activities against leukemic cell lines and animal mouse models, the lack of a consistent supply of the natural product has hampered detailed biological investigations on the compound, including its mode of action and biosynthesis. We report here a significant methodological improvement in the culturing of the bacterium, which allows reliable and steady production of the natural product in good yields. The key experimental step involves the culturing of the strain on dehydrated plates, followed by the generation of a two-stage starter culture and subsequent fermentation of the strain under nutrient-starved conditions. We illustrate use of this culture system by investigating the formation of the enol fragment of the molecule in isotopic labeling experiments with threonine and several advanced precursors (β-ketoamino acid 3, β-hydroxyamino aldehyde 4, and β-ketoaminoaldehyde 5). The results unequivocally show that threonine is the most advanced precursor accepted by the NRPS (non-ribosomal peptidyl synthetase) machinery for final processing and construction of the enol moiety of the natural product.

Total syntheses, fragmentation studies, and antitumor/antiproliferative activities of FR901464 and its low picomolar analogue

FR901464 is a potent anticancer natural product that lowers the mRNA levels of oncogenes and tumor suppressor genes. In this article, we report a convergent enantioselective synthesis of FR901464, which was accomplished in 13 linear steps. Central to the synthetic approach was the diene-ene cross olefin metathesis reaction to generate the C6-C7 olefin without the use of protecting groups as the final step. Additional key reactions include a Zr/Ag-promoted alkynylation to set the C4 Stereocenter, a mild and chemoselective Red-Al reduction, a reagent-controlled stereoselective Mislow-Evans-type [2,3]-sigmatropic rearrangement to install the C5 Stereocenter, a Carreira asymmetric alkynylation to generate the C4′ stereocenter, and a highly efficient ring-closing metathesis-allylic oxidation sequence to form an unsaturated lactone. The decomposition pathways of FR901464's right fragment were studied under physiologically relevant conditions. Facile epoxide opening by β-elimination gave two enones, one of which could undergo dehydration via its hemiketal to form a furan. To prevent this decomposition pathway, a right fragment was rationally designed and synthesized. This analogue was 12 times more stable than the right fragment of the natural product. Using this more stable right fragment analogue, an FR901464 analogue, meayamycin, was prepared in 13 linear steps. The inhibitions of human breast cancer MCF-7 cell proliferation by synthetic FR901464 and meayamycin were studied, and the GI50 values for these compounds were determined to be 1.1 nM and 10 pM, respectively. Thus, meayamycin is among the most potent anticancer small molecules that do not bind to either DNA or microtubule.

Total synthesis of FR901464, an antitumor agent that regulates the transcription of oncogenes and tumor suppressor genes

FR901464 is a potent anticancer agent that regulates the transcription of oncogenes and tumor suppressor genes. A convergent enantioselective synthesis of FR901464 was accomplished in 13 linear steps. Central to the synthetic approach was the diene-ene cr

A New Peptide Bond Surrogate: 2-Isoxazoline in Pseudodipeptide Chemistry

The isoxazoline ring has been incorporated as a new peptide bond surrogate into pseudodipeptide.An easy and versatile general method for the preparation of pseudodipeptides is described.