158612-99-8

Basic information

• Product Name: 2-Oxazolidinone, 4-[(phenylmethoxy)methyl]-, (4S)-
• CAS NO: 158612-99-8
• Molecular Formula: C11H13NO3
• Molecular Weight: 207.229
• Mol File: 158612-99-8.mol

Chemical Properties

• CAS DataBase Reference: 2-Oxazolidinone, 4-[(phenylmethoxy)methyl]-, (4S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Oxazolidinone, 4-[(phenylmethoxy)methyl]-, (4S)-(158612-99-8)
• EPA Substance Registry System: 2-Oxazolidinone, 4-[(phenylmethoxy)methyl]-, (4S)-(158612-99-8)

Safety Data

• Hazardous Substances Data: 158612-99-8(Hazardous Substances Data)

Upstream product

• 32315-10-9 bis(trichloromethyl) carbonate 
• 58577-87-0 O-benzyl-L-serinol 
• 530-62-1 1,1'-carbonyldiimidazole 
• 792158-82-8 (S)-2-amino-4-phenoxybutan-1-ol 
• 4726-96-9 O-Benzyl-L-serine 
• 52161-82-7 O-benzyl-L-serine 
• 46460-82-6 O-benzyl-L-serine methyl ester 
• 23680-31-1 BOC-O-benzyl-L-serine 
• 80963-10-6 methyl O-benzyl-N-(tert-butoxycarbonyl)-L-serinate 
• 66866-45-3 C₂₀H₂₉NO₇ 
• 79069-15-1 N-(tert-butyloxycarbonyl)-O-benzyl-L-serinol 

Downstream Products

• 1357177-74-2 (4S)-4-[(benzyloxy)methyl]-3-(2-hydroxyethyl)-1,3-oxazolidin-2-one 
• 1357177-75-3 S-(2-{(4S)-4-[(benzyloxy)methyl]-2-oxo-1,3-oxazolidin-3-yl}ethyl) ethanethioate 
• 312736-43-9 (S)-4-benzyloxymethyl-2-oxo-oxazolidine-3-carboxylic acid tert-butyl ester 
• 159309-75-8 (S)-4-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyl)-oxazolidin-2-one 

Relevant articles and documents

Synthesis and evaluation of novel modified γ-lactam prostanoids as EP4 subtype-selective agonists

To identify chemically and metabolically stable subtype-selective EP4 agonists, design and synthesis of a series of modified γ-lactam prostanoids has been continued. Prostanoids bearing 2-oxo-1,3-oxazolidine, 2-oxo-1,3-thiazolidine and 5-thioxopyrrolidine as a surrogate for the γ-hydroxycyclopentanone without a troublesome 11-hydroxy group were identified as highly subtype-selective EP4 agonists. Among the tested, several representative compounds demonstrated in vivo efficacy after oral dosing in rats. Their pharmacokinetic and structure-activity relationship studies are presented.

Rearrangements and racemisation during the synthesis of L-serine derived oxazolidin-2-ones

The propensity for N-Boc-4-hydroxymethyl-oxazolidin-2-ones to undergo rapid O-O and N-O carbonyl transfer makes these L-serine derived chiral auxiliaries unsuitable for attachment to polymers.

Polymer supported oxazolidin-2-ones derived from L-serine - A cautionary tale

The capacity of N-Boc-4-hydroxymethyl-oxazolidin-2-ones to undergo rapid O-O and N-O acyl transfer makes these serine derived chiral auxiliaries unsuitable for attachment to polymers. (C) 2000 Elsevier Science Ltd.

Synthesis of the (α,α-difluoroalkyl)phosphonate analogue of phosphoserine

The synthesis of the (α,α-difluoroalkyl)phosphonate analogue of L- phosphoserine, 5, in a form appropriate for solid phase peptide synthesis, is reported. Two independent routes are described, starting from L-serine or (R)-isopropylideneglycerol. In each case, PCF2-C bond formation is achieved by triflate displacement with diethyl lithiodifluoromethylphosphonate.