635313-41-6

Upstream product

• 906448-60-0 (2S,3R)-3-azido-3-(4-methoxyphenyl)-propane-1,2-diol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 159848-93-8 (S)-3-tert-butoxycarbonylamino-3-(4-methoxyphenyl)-1-oxopropane 
• 1059626-59-3 C₂₂H₂₇NO₅ 
• 1059626-61-7 (1R,2S)-[2-benzyloxy-3-hydroxy-1-(4-methoxyphenyl)-propyl]-carbamic acid tert-butyl ester 
• 193073-85-7 methyl (R)-2-((tert-butoxycarbonyl)amino)-2-(4-methoxyphenyl)acetate 
• 159848-74-5 1,1-dimethylethyl (R)-N-[2-hydroxy-1-(4-methoxyphenyl)-ethyl]carbamate 
• 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 
• 57591-61-4 methyl (R)-2-amino-2-(4-hydroxyphenyl)acetate hydrochloride 
• 22818-40-2 D-4-hydroxyphenylglycine 
• 782501-32-0 (2R,3S)-1,2-O-isopropylidene-3-mesyloxy-3-p-methoxyphenyl-1,2-propanediol 
• 782501-33-1 (2S,3R)-3-azido-1,2-O-isopropylidene-3-p-methoxyphenyl-1,2-propanediol 
• 782501-34-2 (2S,3R)-3-amino-1,2-O-isopropylidene-3-p-methoxyphenyl-1,2-propanediol 

Downstream Products

• 635313-42-7 3R-(tert-butoxycarbonyl)-amino-3-(4-methoxyphenyl)-2S-propane-1-(tert-butyl dimethylsiloxy)-2-ol 
• 635313-43-8 2R-amino-1-(tert-butyldimethylsiloxy)methyl-2-(4-methoxyphenyl)-(1R)-ethyl 4-nitrobenzoate 
• 700359-87-1 [3-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-1-(4-methoxy-phenyl)-propyl]-carbamic acid tert-butyl ester 
• 383420-35-7 (2R,3R)-3-tert-butoxycarbonylamino-3-(4-methoxyphenyl)-1,2-propanediol 
• 220736-25-4 (4R,5R)-cytoxazone 
• 220736-25-4 (4R,5S)-5-(hydroxymethyl)-4-(4-methoxyphenyl)-1,3-oxazolidin-2-one 

Relevant academic research and scientific papers

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.

Co(iii)(salen)-catalyzed HKR of two stereocentered alkoxy- and azido epoxides: A concise enantioselective synthesis of (S,S)-reboxetine and (+)-epi-cytoxazone

The HKR of racemic syn- or anti- alkoxy- and azido epoxides catalyzed by Co(salen) complex affords a practical access to a series of enantioenriched syn- or anti- alkoxy- and azido epoxides and the corresponding 1,2-diols. This strategy has been successfully employed in the concise, enantioselective synthesis of bioactive molecules such as (S,S)-reboxetine and (+)-epi-cytoxazone.

An efficient synthesis of (+)-epi-cytoxazone via asymmetric organocatalysis

The catalytic enantioselective synthesis of (+)-epi-cytoxazone has been accomplished in four steps from p-methoxybenzaldehyde N-Boc-imine with good diastereo- and enantioselectivity. This approach involves asymmetric Mannich reaction of an aldehyde with N

Asymmetric synthesis of (+)-epi-cytoxazone

The asymmetric synthesis of (+)-epi-cytoxazone, a stereoisomer of potent cytokine modulator cytoxazone, starting from anisaldehyde in six steps, is described. The required configuration was established via Sharpless kinetic resolution followed by the Mits

A novel stereoselective total synthesis of (+)-5-epi-cytoxazone

Stereoselective synthesis of a potent cytokine modulator cytoxazone isomer has been achieved from 2,3-O-isopropylidene D-glyceraldehyde involving Grignard reaction, subsequent formation of an azide followed by reduction to the aminodiol, and finally cyclization of the N-Boc diol. Copyright

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.

A mild and efficient method for chemoselective deprotection of acetonides by bismuth(III) trichloride

Acetonides undergo chemoselective deprotection to afford the corresponding 1,2-diols in excellent yields using bismuth trichloride in acetonitrile/dichloromethane at ambient temperature.