110905-24-3

Basic information

• Product Name: 2-Oxazolidinone, 3-(bromoacetyl)-4-(phenylmethyl)-, (4R)-
• CAS NO: 110905-24-3
• Molecular Formula: C12H12BrNO3
• Molecular Weight: 298.136
• Mol File: 110905-24-3.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 2-Oxazolidinone, 3-(bromoacetyl)-4-(phenylmethyl)-, (4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Oxazolidinone, 3-(bromoacetyl)-4-(phenylmethyl)-, (4R)-(110905-24-3)
• EPA Substance Registry System: 2-Oxazolidinone, 3-(bromoacetyl)-4-(phenylmethyl)-, (4R)-(110905-24-3)

Safety Data

• Hazardous Substances Data: 110905-24-3(Hazardous Substances Data)

Upstream product

• 22118-09-8 2-bromoacetyl chloride 
• 40217-17-2 (R)-4-(phenylmethyl)-2-oxazolidinone 
• 54896-72-9 (R)-3-phenyl-2-ureido-propionic acid 
• 275378-96-6 (R)-N-Carbamyl-phenylalanine methyl ester 
• 275378-91-1 ((R)-1-Hydroxymethyl-2-phenyl-ethyl)-urea 
• 184714-56-5 (R)-4-benzyl-3-(2-chloroacetyl)oxazolidin-2-one 
• 598-21-0 2-Bromoacetyl bromide 
• 3530-82-3 5-benzyl-hydantoin 

Downstream Products

• 201231-65-4 (R)-4-Benzyl-3-[2-(triphenyl-λ⁵-phosphanylidene)-acetyl]-oxazolidin-2-one 
• 380239-75-8 (4R,3'S,4'R,5'R)-4-Benzyl-3-[5'-(t-butyldimethylsilyloxy)-3'-hydroxy-4'-methylheptanoyl]-2-oxazolidinone 
• 714974-10-4 (3'S,4R,4'S,6'S,8'R,10'S)-4-benzyl-3-[3'-hydroxy-4',6',8',10'-tetramethyl-11'-(tetrahydropyran-2''-yloxy)undecanoyl]-2-oxazolidinone 
• 1174528-02-9 C₂₀H₂₁NO₅ 
• 137789-54-9 [2-(4-benzyl-2-oxo-oxazolidin-3-yl)-2-oxo-ethyl]-phosphonic acid diethyl ester 
• 113122-43-3 Methyl-carbamic acid (E)-(1S,2R)-1-[(R)-2-((R)-4-benzyl-2-oxo-oxazolidin-3-yl)-1-bromo-2-oxo-ethyl]-2-methyl-hex-4-enyl ester 
• 136620-81-0 (4R)-3-((2'S,3'S)-2'-azido-3'-hydroxy-3'-phenylpropanoyl)-4-(phenylmethyl)-2-oxazolidinone 
• 110905-26-5 (4R)-3-((2'S,3'S)-2'-azido-3'-hydroxy-4'-methyl-4'-pentenoyl)-4-(phenylmethyl)-2-oxazolidinone 

Relevant articles and documents

Towards the total synthesis of marineosin A: Construction of the macrocyclic pyrrole and an advanced, functionalized spiroaminal model

Herein, we describe the enantioselective construction of the 12-membered macrocyclic pyrrole core of marineosin A in 5.1 % overall yield from (S)-propylene oxide. The route features a key Stetter reaction to install a 1,4-diketone, which is subjected to Paal-Knorr pyrrole synthesis and ring-closing metathesis to afford the macrocycle. A divergence point in the synthetic scheme also enabled access to a highly functionalized spiroaminal model system through an acid-mediated hydroxy oxo amide cyclization strategy. Copyright

A short approach to the bicyclo[4.3.0]nonane fragment of stawamycin

The bicyclo[4.3.0]nonane (C11-C21) fragment of stawamycin has been prepared by a sequence involving 11 steps (10% overall yield) from methyl (R)-(-)-3-hydroxy-2-methylpropionate. Key steps are a Pd-catalysed Stille coupling reaction

Total synthesis of a stereoisomer of bistramide C and assignment of configuration of the natural product

After the isolation of the bioactive polyether bistramide C from the marine ascidian Lissoclinum bistratum in 1988, NMR spectroscopic investigations over the next 12 years reduced the total number of possible stereoisomers of this compound from 1024 to 32. Based on the preparation of segments of the natural product as well as the total synthesis of a randomly selected stereoisomer of bistramide C, the stereochemical puzzle could be further simplified to eight possible stereoisomers. A convergent three-segment coupling strategy, the use of a common, D-glucose-derived intermediate for the preparation of pyran rings in two segments, a stereoselective photo-spiroketalization, and the use of azides to minimize protective group manipulations before segment couplings are highlights of the synthetic approach. The total synthesis also provided the key segments for a chiroptical analysis according to van't Hoff's principle of optical superposition, which was crucial for the assignment of a sole relative and absolute configuration of the natural product. Bistramide C represents therefore the first member of this class of structurally unusual marine polyethers whose configuration is known as a result of the combined use of synthetic and chiroptical tools.