468773-16-2

Basic information

• Product Name: N-(2-nitrobenzenesulfonyl)-O-(tert-butyl)-(S)-serine methyl ester
• Synonyms: N-(2-nitrobenzenesulfonyl)-O-(tert-butyl)-(S)-serine methyl ester
• CAS NO: 468773-16-2
• Molecular Weight: 360.388
• Mol File: 468773-16-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N-(2-nitrobenzenesulfonyl)-O-(tert-butyl)-(S)-serine methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-nitrobenzenesulfonyl)-O-(tert-butyl)-(S)-serine methyl ester(468773-16-2)
• EPA Substance Registry System: N-(2-nitrobenzenesulfonyl)-O-(tert-butyl)-(S)-serine methyl ester(468773-16-2)

Safety Data

• Hazardous Substances Data: 468773-16-2(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 71989-33-8 Fmoc-Ser(tBu)-OH 
• 1694-92-4 2-Nitrobenzenesulfonyl chloride 
• 17114-97-5 O-tert-butyl-L-serine methyl ester hydrochloride 

Downstream Products

• 856865-69-5 N-methyl-N-(o-nitrobenzenesulfonyl)-O-t-butyl-L-serine methyl ester 
• 856865-91-3 N-α-methyl-N-α-(o-nitrobenzenesulfonyl)-O-t-butyl-L-serine 
• 468773-61-7 1-benzyl-7-tert-butoxymethyl-octahydro-isoxazolo[3,4-c]pyridine 
• 468773-32-2 N-(but-3-enyl)-O-(tert-butyl)-N-(2-nitrobenzenesulfonyl)-(S)-serinal 
• 468773-50-4 1-benzyl-7-tert-butoxymethyl-6-(2-nitrobenzenesulfonyl)-octahydro-isoxazolo[3,4-c]pyridine 

Relevant articles and documents

Environmentally Friendly SPPS II: Scope of Green Fmoc Removal Protocol Using NaOH and Its Application for Synthesis of Commercial Drug Triptorelin

With the growing necessity to consider environmental impacts when synthesizing peptide-based drugs and to expand upon the recently published short communication report, we herein present a thorough evaluation of a green Fmoc removal protocol. Our protocol avoids the use of hazardous components (using piperidine as a base and dichloromethane (DCM) and N,N-dimethylformamide (DMF) as solvents) and relies on the utilization of the green mineral base NaOH in combination with the greener solvent 2-methyltetrahydrofuran (2-MeTHF) mixed with MeOH. For the original Fmoc removal cocktail (solvents ratio of 1:1), we evaluated the impact of quality/purity of the used 2-MeTHF, scale-up, ratio of 2-MeTHF/MeOH, utilized hydroxide, temperature, and reaction time. An alternative 3:1 protocol was examined using various amino acids, and only Gly required the optimization of the Fmoc removal cocktail composition. The optimized protocol used to remove Fmoc from Gly residue was proved by the synthesis of Leu-enkephalin. We also investigated the stability of the conventional amino acid side-chain-protecting groups, t-Bu, Boc, Trt, and Pbf, and the formation of aspartimide as an undesirable side reaction that occurs during Fmoc solid-phase peptide synthesis (SPPS). The applicability of this synthesis strategy was documented by evaluating the SPPS of a commercial drug used for prostate and breast cancer treatments - decapeptide triptorelin.

Amino acid derived intramolecular 1,3-dipolar cycloadditions that form bridged medium ring systems with diastereoselective control

Intramolecular nitrone cycloadditions using amino acid precursors, generate aminohydroxyazepine and amino hydroxypiperidine templates. The cycloaddition reactions yield either a [4.3.0] fused system or in most cases a [4.2.1] bridged system. The [4.2.1] bridged system allows for the stereospecific preparation of 3-amino-5-hydroxyazepines while the [4.3.0] system allows for the preparation of 3-amino-5-hydroxymethyl piperidines.