69942-12-7

Usage

Uses

Used in Pharmaceutical Industry:
N-BOC-DL-SERINE is used as a key intermediate in the synthesis of dehydroamino acids, which are important for the development of inhibitors and other pharmacologically active compounds. These compounds have potential applications in the treatment of various diseases and disorders.
Used in Antibacterial Applications:
N-BOC-DL-SERINE is used as a precursor in the preparation of thiopeptide antibiotic Amythiamicin D, which is effective against methicillin-resistant Staphylococcus aureus (MRSA) and malaria. This antibiotic offers a promising alternative for treating drug-resistant bacterial infections and combating malaria.

Physical Form

Liquid or Solid or Semi-solid

InChI:InChI=1/C9H17NO5/c1-9(2,3)15-8(13)10-6(5-11)7(12)14-4/h6,11H,5H2,1-4H3,(H,10,13)

Upstream product

• 2104-89-4 Ser-OMe 
• 24424-99-5 di-tert-butyl dicarbonate 
• 3850-40-6 N-Boc-DL-serine 
• 74-88-4 methyl iodide 
• 61137-10-8 (trimethylsilyl)diazirine 
• 4248-19-5 tert-butyl carbazate 
• 1415303-95-5 C₁₈H₂₉NO₂Si 
• 100038-76-4 methyl 2-(tert-butoxycarbonylamino)-3-pentenoate 
• 1291065-78-5 tert-butyl {2,3-dimethyl-1-(phenylsulfonyl)but-2-en-1-yl}carbamate 
• 113525-84-1 2-Oxo-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester 
• 5619-04-5 methyl 2-amino-3-hydroxypropanoate hydrochloride 
• 113525-83-0 methyl N-Boc-2-oxazolidinone-4-carboxylate 

Downstream Products

• 106693-44-1 4-(R,S)-(t-butoxycarbonylamino)-3-oxo-1,2-diazolidine 
• 870820-64-7 Methyl 2-(tert-butoxycarbonylamino)-3-(tert-butyldiphenylsilyloxy)propanoate 
• 157604-46-1 3-tert-butyl 4-methyl 2,2-dimethyl-1,3-oxazolidine-3,4-dicarboxylate 
• 95715-86-9 (S)-2,2-dimethyl-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester 4-methyl ester 
• 170848-34-7 methyl 2-[(tert-butoxycarbonyl)amino]-3-iodopropanoate 
• 869646-27-5 C₁₆H₂₃NO₄Se 
• 175844-11-8 methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-bromopropionate 
• 94790-24-6 (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(4-methoxyphenyl)propanoate 
• 524940-52-1 3-(bis-benzyloxy-phosphoryl)-2-[3-(bis-benzyloxy-phosphoryl)-2-tert-butoxycarbonylamino-propionylamino]-propionic acid methyl ester 
• 524940-51-0 3-(bis-benzyloxy-phosphoryl)-2-tert-butoxycarbonylamino-propionic acid 
• 524940-50-9 3-(bis-benzyloxy-phosphoryl)-2-tert-butoxycarbonylamino-propionic acid methyl ester 
• 601507-18-0 C₂₆H₃₁N₅O₆ 
• 601507-14-6 C₂₀H₂₇N₅O₆ 
• 601507-16-8 [2-(acetyl-methyl-amino)-1-benzyl-4-oxo-1,4,5,6-tetrahydro-pyrimidin-5-yl]-methyl-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Identification of fonofos metabolites in Latuca sativa, Beta vulgaris, and Triticum aestivum by packed capillary flow fast atom bombardment tandem mass spectrometry.

The metabolism of fonofos, a thiophosphonate insecticide, was investigated in mature lettuce (Latuca sativa), beet (Beta vulgaris), and wheat (Triticum aestivum). Six new metabolites were identified by LC-MS and LC-MS-MS analysis using fast atom bombardment (FAB) and packed capillary LC columns with application of the on-column focusing technique. These methods provided the sensitivity required to identify unknown metabolites that were present in the mature plants at only 20-230 ppb. Structural elucidation was facilitated by use of fonofos labeled with both carbon-14 and carbon-13 in the phenyl ring. In all three plants fonofos was converted to a glucose conjugate of thiophenoxylactic acid. Oxidation of the glucose conjugate gave isomeric sulfoxides in all species examined. Thiophenoxylactic acid was found esterified to malonic acid in lettuce. In beets, S-phenylcysteine was found as its malonic acid amide. A second metabolite unique to beets was N-(malonyl)-[2[(ethoxyethylphosphinothionyl)oxy]phenyl]cysteine. This novel structure was confirmed by synthesis.

Method for synthesizing benserazide hydrochloride by utilizing fixed bed hydrogenation equipment

The invention discloses a method for synthesizing benserazide hydrochloride by using fixed bed hydrogenation equipment, which is characterized in that a compound 1 reacts with an amino protective agent to carry out an amino protection reaction, so that the subsequent purification is easy, and the dosage of hydrazine hydrate in the synthesis method is small; according to the method, fixed bed hydrogenation equipment is used for synthesis, a fixed bed reactor is filled with a solid catalyst or a solid to realize a heterogeneous reaction process, the catalyst in the fixed bed reactor is relatively fixed, a reaction liquid flows through a bed layer, and the reaction liquid flows through the bed layer by adjusting the flow rate and the reaction pressure; qualified products can be obtained after reaction liquid flows out of the fixed bed, continuous production can be achieved, product deterioration caused by long-time contact of the products and the catalyst can be avoided, the same amount of products can be produced due to continuous production, the reactor size can be very small, the safety problem caused by high-pressure reaction is greatly reduced, the amount of the catalyst used in the reaction is less, and the production cost is reduced.

Discovery of 3-Quinazolin-4(3 H)-on-3-yl-2, N-dimethylpropanamides as Orally Active and Selective PI3Kα Inhibitors

Phosphoinositide 3-kinases (PI3Ks) mediate a series of events related to cell growth, proliferation, survival, and differentiation. Overexpression of PI3Ks can lead to the dysregulation of cell homeostasis and cause tumorigenesis. In this study, rationally designed compounds were investigated as PI3Kα-selective inhibitors. Our efforts culminated in the discovery of a series of quinazolin-4(3H)-one derivatives with 2-substituted-N-methylpropanamide substitutions as PI3Kα-selective inhibitors. The best compound, 10, has PI3Kα enzymatic and cellular IC50 values of 1.8 and 12.1 nM, respectively. It exhibits biochemical selectivities for PI3Kα over PI3Kβ/δ/γof 150/7.72/7.67-fold and cellular selectivities of 115/15.1/>826-fold, respectively. Compound 10 is 59% orally bioavailable with a dose-normalized AUC of 3090 nM. These effects translated into in vivo conditions, as 10 significantly time- and dose-dependently inhibited phosphorylation of Akt in BT-474 subcutaneous xenograft mice and inhibited tumor growth.

Quinazolinone Compound and Application Thereof

The present invention relates to a series of quinazolinone compounds and applications thereof as PI3Kα inhibitors. In particular, the present invention relates to a compound shown in formula (I) and a tautomer or pharmaceutically acceptable salt thereof.

Synthesis method of benserazide hydrochloride

The invention relates to a synthesis method of benserazide hydrochloride. According to the synthesis method, serine methyl ester hydrochloride is taken as the primary raw material, at first, amino protection reactions are carried out; and then amine-ester exchange reactions, condensation reactions, reduction reactions, and de-protection reactions are performed to obtain high purity benserazide hydrochloride. The synthesis method has the advantages that the raw materials are cheap and easily available, the operation is convenient, the product purity and yield of each step are high, and thus thesynthesis method is suitable for industrial production.

Improved synthetic routes to the selenocysteine derivatives useful for Boc-based peptide synthesis with benzylic protection on the selenium atom

Selenocysteine (Sec) derivatives, i.e., Boc-Sec(MBn)-OH (1) and Boc-Sec(MPM)-OH (2), which are useful for chemical synthesis of selenopeptides, were obtained from L-serine in five steps with total yields of 73% and 74%, respectively. The enantiomeric excesses were confirmed to be >99% e.e. by optical resolution using a chiral column on HPLC. On the other hand, for the case of a Fmoc-protected Sec derivative, i.e., Fmoc-Sec(MPM)-OH, similar reactions resulted in low yields and partial racemization taking place. [PRESENTED EQUATION]

Efficient Synthesis of N-Sulfonyl β -Arylmethylalaninates from Serine via Ring Opening of N-Sulfonyl Aziridine-2-carboxylate

We report the efficient synthesis of N-sulfonyl β-arylalanines methyl ester through regioselective ring opening of N-protected aziridines by variety of heteroaryl C-nucleophiles. We have optimized synthesis of N-protected aziridines with versatile protecting groups to afford 4a-c, 6a, and 6b with moderate to good yields using sulfuryl chloride, triethyl amine, and toluene at -50 °C. The present work reports on the studies related to electronic effect of nitrogen substituent on aziridination from the inexpensive starting material DL-serine. The present investigation also reports the efficient synthesis of N-sulfonyl β-arylmethylalaninates (7a-e and 8a-e) by regioselective nucleophilic ring opening of N-sulfonamido-protected aziridines using various aryl moieties such as C-nucleophiles and Lewis acids (InCl3, FeCl3, Cu(OTf)2) as catalysts and some trials by ring opening using Grignard reagent. GRAPHICAL ABSTRACT.

1,3,4-OXADIAZOLE AND 1,3,4-THIADIAZOLE BETA-LACTAMASE INHIBITORS

β-Lactamase inhibitor compounds (BLIs) are disclosed, including compounds that have activity against class A, class C or class D β-lactamases. Methods of manufacturing the BLIs, and uses of the compounds in the preparation of pharmaceutical compositions and antibacterial applications are also disclosed.

One-pot synthesis of α-amino acids from CO2 using a bismetal reagent with Si-B bond

In the presence of 1.1 equiv of PhMe2Si-Bpin, 5 equiv of CsF, and 20 mol % of TsOH·H2O, precursors of N-Boc-imines can be converted into the corresponding α-aryl or α-alkenyl glycine derivatives under gaseous CO2 in moderate-to-high yields with a single operation. α-Isobutenyl glycine thus obtained can be further derivatized into various types of α-amino acids including N-Boc-leucine, serine, and glycine derivatives in short steps.

Fluorinated cyclopropane analogs of glutamic acid

The present invention relates to a compound of the following formula (I): or a pharmaceutically acceptable salt, a stereoisomer or a mixture in all proportions of stereoisomers thereof, in particular a mixture of enantiomers, such as a racemic mixture, wh