458531-57-2

Basic information

• Product Name: Carbamic acid, [(1S)-1-methyl-2-oxo-3-butenyl]-, 1,1-dimethylethyl ester (9CI)
• Synonyms: Carbamic acid, [(1S)-1-methyl-2-oxo-3-butenyl]-, 1,1-dimethylethyl ester (9CI)
• CAS NO: 458531-57-2
• Molecular Formula: C₁₀H₁₇NO₃
• Molecular Weight: 199.24688
• Product Categories: N-BOC
• Mol File: 458531-57-2.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Carbamic acid, [(1S)-1-methyl-2-oxo-3-butenyl]-, 1,1-dimethylethyl ester (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [(1S)-1-methyl-2-oxo-3-butenyl]-, 1,1-dimethylethyl ester (9CI)(458531-57-2)
• EPA Substance Registry System: Carbamic acid, [(1S)-1-methyl-2-oxo-3-butenyl]-, 1,1-dimethylethyl ester (9CI)(458531-57-2)

Safety Data

• Hazardous Substances Data: 458531-57-2(Hazardous Substances Data)

Upstream product

• 458531-56-1 2(S)-tert-butyloxycarbonylamino-3(R,S)-hydroxypent-4-ene 
• 79069-50-4 Boc-Ala-H 
• 1826-67-1 vinyl magnesium bromide 
• 146553-06-2 tert-butyl {(S)-1-[methoxy(methyl)amino]-1-oxopropan-2-yl}carbamate 
• 15761-38-3 L-N-Boc-Ala 
• 593-60-2 Vinyl bromide 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 1294446-95-9 tert-butyl ((2S,3R,E)-3-hydroxy-6-phenylhex-4-en-2-yl)carbamate 
• 1294447-22-5 N-((2S,3R,E)-3-hydroxynon-4-en-2-yl)-2-phenylacetamide 
• 1294447-24-7 (2S,3R,E)-2-amino-6-phenylhex-4-en-3-ol 
• 1294447-25-8 N-((2S,3R,E)-3-hydroxy-6-phenylhex-4-en-2-yl)acetamide 
• 1294447-26-9 N-((2S,3R,E)-3-hydroxy-6-phenylhex-4-en-2-yl)-2-phenylacetamide 
• 1294447-27-0 N-((2S,3R,E)-3-hydroxy-6-phenylhex-4-en-2-yl)octanamide 
• 458531-64-1 1-acetylsulfanyl-3(S)-(benzoyl-glycyl-prolyl-leucyl)amino-3-oxopentane 

Relevant articles and documents

Synthesis and characterization of some atypical sphingoid bases

Sphingolipids are ubiquitous and abundant components of all eukaryotic and some prokaryotic organisms. Sphingolipids show a large structural variety not only between the different species, but also within an individual cell. This variety is not limited to alterations in the polar headgroups of e.g. glycosphingolipids, but also affects the lipophilic anchors comprised of different fatty acids on the one hand and different sphingoid bases on the other hand. The structural variations within different sphingoid bases e.g. in pathogens can be used to identify novel biomarkers and drug targets and the specific change in the profile of common and uncommon sphingolipids are associated with pathological conditions like diabetes or cancer. Therefore, the emerging field of sphingolipidomics is dedicated to collect data on the sphingolipidome of a cell and hence to assign changes therein to certain states of a cell or to pathological conditions. This powerful tool however is still limited by the availability of structural information about the individual lipid species as well as by the availability of appropriate internal standards for quantification. Herein we describe the synthesis of a variety of 1-deoxy-sphingoid bases. 1-DeoxySphingolipids have recently acquired significant attention due to its pathological role in the rare inherited neuropathy, HSAN1 but also as predictive biomarkers in diabetes type II. Some of the compounds synthesized and characterized herein, have been used and will be used to elucidate the correct structure of these disease-related lipids and their metabolites.

An enantioselective synthesis of the bicyclic core of the marine natural product awajanomycin

A concise stereoselective synthesis of the N-benzylated bicyclic core of the marine natural product awajanomycin is described starting with naturally occurring l-alanine. Key steps in the synthesis include a ring-closing metathesis to establish a δ-lactam ring followed by a stereoselective hydroxylation to instal the quaternary centre.