383420-35-7

Upstream product

• 922728-71-0 (4R,5R)-4-(4-Methoxy-phenyl)-2,2-dioxo-2λ⁶-[1,2,3]oxathiazinan-5-ol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 22818-40-2 D-4-hydroxyphenylglycine 
• 57591-61-4 methyl (R)-2-amino-2-(4-hydroxyphenyl)acetate hydrochloride 
• 700359-87-1 [3-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-1-(4-methoxy-phenyl)-propyl]-carbamic acid tert-butyl ester 
• 383420-34-6 (2R,3R)-3-benzylamino-N-tert-butoxycarbonyl-3-(4-methoxyphenyl)-1,2-propanediol 
• 159848-93-8 (S)-3-tert-butoxycarbonylamino-3-(4-methoxyphenyl)-1-oxopropane 
• 383420-33-5 (2R,3R)-3-benzylamino-N-tert-butoxycarbonyl-1,2-O-isopropylidene-3-(4-methoxyphenyl)-1,2-propanediol 
• 383420-32-4 (2R,3R)-3-benzylamino-1,2-O-isopropylidene-3-(4-methoxyphenyl)-1,2-propanediol 
• 635313-43-8 2R-amino-1-(tert-butyldimethylsiloxy)methyl-2-(4-methoxyphenyl)-(1R)-ethyl 4-nitrobenzoate 
• 850166-76-6 (R)-(1-(4-methoxyphenyl)-2-oxoethyl) tert-butyl carbamate 
• 143323-49-3 (R)-methyl 2-((tert-butoxycarbonyl)amino)-2-(4-hydroxyphenyl)acetate 
• 848477-96-3 4-[(2R,3R)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-(4-methoxyphenyl)-1-oxopropyl]morpholine 
• 848477-64-5 4-[(2R,3R)-3-azido-2-hydroxy-3-(4-methoxyphenyl)-1-oxo-propyl]morpholine 

Downstream Products

• 220736-25-4 (4R,5R)-cytoxazone 

Relevant academic research and scientific papers

Diastereoselective Radical Couplings Enable the Asymmetric Synthesis of anti-β-Amino-α-hydroxy Carboxylic Acid Derivatives

anti-β-Amino-α-(aminoxy) esters or amides are synthesized by merging polar asymmetric aza-Michael additions of lithium 1-phenylethylamides to α,β-unsaturated carboxylic acid derivatives and diastereoselective radical couplings with the persistent free rad

Proline-catalyzed α-aminooxylation of β-amino aldehydes: Access to enantiomerically pure syn - And anti -3-Amino-3-aryl-1,2-alkanediols

A new synthetic method for enantioselective synthesis of syn or anti-3-amino-3-aryl-1,2-alkanediols via proline catalyzed α-aminooxylation of β-amino aldehydes are described. This methodology is successfully applied to a concise and protecting group-free asymmetric synthesis of (-)-cytoxazone, (+)-epi-cytoxazone and formal synthesis of N-thiolated 2-oxazolidinone.

NaIO4-mediated asymmetric bromohydroxylation of α,β-unsaturated carboxamides with high diastereoselectivity: a short route to (-)-cytoxazone and droxidopa

The NaIO4-mediated asymmetric bromohydroxylation of α,β-unsaturated carboxamides was achieved using lithium bromide as the bromine source under acidic conditions at rt to afford the corresponding chiral α-bromo-β-hydroxy carboxamides. Excellent

Enantioselective synthesis of (-)-cytoxazone and (+)-epi-cytoxazone via Rh-catalyzed diastereoselective oxidative C-H aminations

An efficient enantioselective synthesis of (-)-cytoxazone (1) and (+)-epi-cytoxazone (2) using proline-catalyzed asymmetric α-amino-oxylation of aldehydes followed by Rh-catalyzed diastereoselective oxidative C-H amination as the key steps is described. s

Synthesis of 2-oxazolidinones from β-lactams: Stereospecific total synthesis of (-)-cytoxazone and all of its stereoisomers

The synthetic correlation between two different antibiotic frameworks, the β-lactams and 2-oxazolidinones, is described for the first time. In this approach, 2-oxazolidinones are prepared in stereomerically pure form from 3-hydroxy β-lactams by a ring-ope

Dynamic ligand exchange of the lanthanide complex leading to structural and functional transformation: One-pot sequential catalytic asymmetric epoxidation-regioselective epoxide-opening process

The characteristic property of the lanthanide complex, which easily undergoes a dynamic ligand exchange and alters its structure and function in situ, is described. After the completion of the catalytic asymmetric epoxidation of various α,β-unsaturated amides 2 in the presence of the Sm-(S)-BINOL-Ph3-As=O (1:1:1) complex 1 (2-10 mol %), the addition of Me3SiN3 directly to the reaction mixture led to smooth epoxide-opening at room temperature, affording the corresponding anti-β-azido-α-hydroxyamide 4 in excellent overall yield (up to 99%) with complete regioselectivity and excellent enantiomeric excess (up to >99%). The key to the success of the sequential process was the in situ generation of the highly reactive samarium azide complex through dynamic ligand exchange. In situ IR spectroscopy and other experiments provided strong evidence that the samarium azide complex was generated. In addition, the relatively high Lewis basicity of the amide moiety had a key role in the high reactivity of both the epoxidation and the epoxide-opening reactions. Examinations of other nucleophiles such as sulfur or carbon nucleophiles as well as transformations of epoxide-opened products are also described.

Stereoselective synthesis of (-)-cytoxazone and (+)-5-epi-cytoxazone

A novel, stereo selective synthesis of (-)-cytoxazone 1a and stereoselective synthesis of (+)-5-epi-cytoxazone 1b were achieved via stereoselective Grignard addition of vinylmagnesium bromide on N-Boc aldehyde obtained from p-hydroxy-D-phenylglycine 2 followed by cyclization of N-Boc alcohol 6, ozonolysis and reduction to get (+)-5-epi-cytoxazone. Compound 6 underwent mitsunobu conditions, deprotection of ester followed by cyclization of N-Boc alcohol to get (-)-cytoxazone.

Stereoselective synthesis of (-)-cytoxazone

A novel stereoselective synthesis of (-)-cytoxazone 1 was achieved via addition of p-methoxyphenylmagnesium bromide to the benzylimine derived from (S)-2,3-O-isopropylidene glyceraldehyde followed by one-step regioselective cyclization of N-Boc amino diol