195624-97-6

Upstream product

• 60512-85-8 (E)-isopropyl cinnamate 
• 79-15-2 N-bromoacetamide 
• 7780-06-5 isopropyl cinnamate 
• 140-10-3 (E)-3-phenylacrylic acid 

Downstream Products

• 32981-85-4 methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate 
• 136561-53-0 (2R,3S)-2-hydroxy-3-amino-3-phenylpropionic acid 
• 157240-36-3 (2R,3S)-3-phenylisoserine methyl ester 
• 153652-70-1 (4S,5R)-3-Benzoyl-2,2-dimethyl-4-phenyl-1,3-oxazolidine-5-carboxylic acid 
• 202390-84-9 Methyl (4S,5R)-3-benzoyl-2,2-dimethyl-4-phenyl-1,3-oxazolidine-5-carboxylate 
• 607394-06-9 (4S,5R)-3-Acetyl-2,2-dimethyl-4-phenyl-oxazolidine-5-carboxylic acid 
• 150949-07-8 methyl (2S,3S)-phenylisoserine 
• 158830-39-8 methyl (2S,3S)-2-hydroxy-3-(N-tert-butoxycarbonylamino)-3-phenylpropanoate 
• 274681-82-2 (4S,5S)-5-(isopropoxycarbonyl)-2-methyl-4-phenyl-2-oxazoline 
• 274681-83-3 (4S,5R)-5-(isopropoxycarbonyl)-2-methyl-4-phenyl-2-oxazoline 
• 274681-84-4 isopropyl (2S,3S)-3-(acetylamino)-2-azido-3-phenylpropionate 
• 274681-94-6 methyl (2S,3S)-2-amino-3-[(tert-butoxycarbonyl)amino]-3-phenylpropanoate 
• 274681-92-4 methyl (2S,3S)-2-azido-3-(tert-butoxycarbonylamino)-3-phenylpropionate 
• 274681-91-3 methyl (2S,3S)-2-azido-3-(benzoylamino)-3-phenylpropionate 

Relevant academic research and scientific papers

Heterogeneous asymmetric aminohydroxylation of alkenes using a silica gel-supported bis-cinchona alkaloid

Excellent enantioselectivities of up to > 99% ee have been achieved in the heterogeneous asymmetric aminohydroxylation of trans-cinnamate derivatives using silica gel-supported (QN)2PHAL [SGS-(QN)2PHAL 1]; the dark brown 1·Os complex

Concentration dependence of the sharpless asymmetric amidohydroxylation of isopropyl cinnamate

(Equation presented) A need to prepare large quantities of phenylisoserine for the semisynthesis of paclitaxel prompted us to examine the Sharpless amidohydroxylation reaction to see if it could be run at concentrations greater than those reported in the literature. During these investigations, we discovered that the amount of amidoalcohol produced in the reaction decreased while the diol side product increased as the concentration increased. We discovered that acetamide suppresses this side reaction and allows us to run the chemistry at 0.1 g/mL rather than the 0.014 g/mL reported in the literature.

An asymmetric aminohydroxylation route to (+)-L-733,060

An enantioselective synthesis of (+)-L-733,060 starting from cinnamic acid using Sharpless asymmetric aminohydroxylation and Wittig reactions as the key steps is described.

A highly efficient and practical new PEG-bound bi-cinchona alkaloid ligand for the catalytic asymmetric aminohydroxylation of alkenes

A new recyclable PEG-bound bi-cinchona alkaloid ligand has been developed for homogeneous catalytic asymmetric aminohydroxylation; it can be easily recovered by precipitation and reused more than five times without any significant loss in its catalytic efficiency.

Osmylated macroporous resins: Safe, highly efficient and recyclable catalysts for asymmetric aminohydroxylation of olefins

Osmylated macroporous resins displayed excellent catalytic performances in the asymmetric aminohydroxylation of olefins and, moreover, these resins were easily recovered and reused without any significant decrease in catalytic efficiencies.

The design and synthesis of guanosine compounds with in vitro activity against the colon cancer cell line SW480: Non-taxane derived mimics of taxol?

In the course of our investigation into the use of taxol as a lead compound to design new molecules with anti-cancer activity, we have synthesized four compounds based on protected guanosine coupled to taxol isoserine side-chain analogues. These analogues show in vitro anti-cancer activity against the colon cancer cell line SW480 that their constituent parts do not.

Preparation of β-amino-α-mercapto acids and amides: Stereocontrolled syntheses of 2′-sulfur analogues of the taxol C-13 side chain, both syn and anti S-acetyl-N-benzoyl-3-phenylisocysteine

Stereoselective syntheses of both syn and anti S-acetyl-N-benzoyl-3-phenylisocysteine as coupling-ready reagents via the ring-opening reactions of trans- and cis-oxazoline-5-carboxylates with thiolacetic acid were demonstrated. In addition, we report upon ring-opening reactions of oxazoline-5-carboxamides. Ab initio molecular calculations were used to explain the different reactivities of these oxazolines with respect to the ring-opening reaction.

Aminohydroxylation of olefins in the presence of acetamide

The present invention is a process to prepare on of a phenylisoserine ester of the formula (II) φ-CH(NH—CO—CH3)—CH(OH)—CO—O—R1 with reduced amount of diol by-product by the use of a compound of the formula R2—CO—NH2 where R2 is C1-C6 alkyl with the proviso that R2 is not tertiary.

Efficient asymmetric synthesis of 2,3-diamino-3-phenylpropanoic acid derivatives

An efficient, stereoselective synthesis of selectively-protected anti and syn, methyl 2-amino-3-(Boc-amino)-3-phenylpropanoate is described. Preparation of syn β-acetylamino-α-hydroxy ester was from isopropyl cinnamate via an acetamide-based Sharpless ami

Efficient syntheses and ring-opening reactions of trans- and cis-Oxazoline-5-carboxylates

cis- and trans-Oxazoline-5-carboxylates were synthesized effeciently from isopropyl trans-cinnamate utilizing the sharpless AA reaction. trans-Oxazoline was much more reactive than the cis-isomer toward ring opening reactions. From ab initio molecular calculation, the cis-isomer was predicted to be less reactive than the trans-isomer by 2.7 kcal/mol. Both syn and anti acetylthio ester and anti diamino ester were synthesized from these cis- and trans- oxazoline-5-carboxylates.