99528-64-0

Basic information

• Product Name: cis-2,3-epoxy-3-phenyl-1-propanoic acid
• Synonyms: cis-2,3-epoxy-3-phenyl-1-propanoic acid
• CAS NO: 99528-64-0
• Molecular Weight: 164.161
• Mol File: 99528-64-0.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: cis-2,3-epoxy-3-phenyl-1-propanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: cis-2,3-epoxy-3-phenyl-1-propanoic acid(99528-64-0)
• EPA Substance Registry System: cis-2,3-epoxy-3-phenyl-1-propanoic acid(99528-64-0)

Safety Data

• Hazardous Substances Data: 99528-64-0(Hazardous Substances Data)

Upstream product

• 99528-65-1 (2R,3R)-(+)-methyl 3-phenyloxiranecarboxylate 
• 126060-73-9 ethyl (2R,3R)-3-phenyl-2,3-oxiranepropanoate 
• 124649-67-8 methyl (2S,3R)-3-phenyl-2,3-dihydroxypropanoate 
• 124605-43-2 (2S,3R)-(-)-methyl 3-hydroxy-3-phenyl-2-((p-tolylsulfonyl)oxy)propionate 
• 103-26-4 Methyl cinnamate 
• 4610-69-9 (Z)-ethyl cinnamate 
• 77-92-9 citric acid 

Downstream Products

• 174729-12-5 13-O-((2R,3R)-3-phenylglycidoyl)-7,10-O,O'-bis(2,2,2-trichloroethoxycarbonyl)-10-deacetylbaccatin 
• 114915-20-7 Docetaxel 
• 114915-14-9 7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel 
• 174729-13-6 C₄₄H₄₅Cl₆N₃O₁₆ 
• 212910-87-7 C₅₁H₅₃Cl₆NO₁₇ 
• 145432-51-5 (βR)-N-(tert-butoxycarbonyl)-β-methyl-L-phenylalanine 
• 91828-71-6 (2R,3R)-2-Hydroxy-3-phenylbutyric acid methyl ester 
• 198493-85-5 (2R,3R)-2-[(tert-butoxycarbonyl)amino]-3-phenylbutanoic acid 
• 117486-31-4 (2S,3R)-2-Hydroxy-3-phenylbutyric acid methyl ester 
• 197714-21-9 methyl (2S,3R)-2-(methanesulfonyloxy)-3-phenylbutanoate 
• 197714-07-1 methyl (2R,3R)-2-(methanesulfonyloxy)-3-phenylbutanoate 
• 197714-31-1 (2R,3R)-2-[(tert-butoxycarbonyl)amino]-3-phenylbutanol 
• 197714-18-4 methyl (2S,3R)-2-[(tert-butoxycarbonyl)amino]-3-phenylbutanoate 
• 197714-29-7 methyl (2R,3R)-2-[(tert-butoxycarbonyl)amino]-3-phenylbutanoate 

Relevant articles and documents

Synthesis of taxoids 4. Novel and versatile methods for preparation of new taxoids by employing cis- or trans-phenyl glycidic acid

A novel route to the synthesis of docetaxel using esterification of (2R,3R)-or (2R,3S)-glycidic acid with 7,10-bis-O-(2,2,2- trichloroethoxycarbonyl)-10-deacetylbaccatin III is described. Related novel taxoids which have new side chains were synthesized from these synthetic intermediates.

A Catalytic Asymmetric Synthesis of N-Boc-β-Methylphenylalanines

An efficient, stereodivergent, and enantioselective synthesis of the syn and anti diastereomers of N-Boc-β-methylphenylalanine has been developed. Starting from enantiomerically pure (2S,3S)-2,3-epoxy-3-phenyl-1-propanol, a three-step sequence, consisting of the oxidation of the primary alcohol up to the carboxyl stage, ring opening of the epoxy acid with Me2CuCNLi2, and esterification of the resulting hydroxy acid with methyl iodide, leads to the hydroxy ester anti-W, which has been converted in a stereodivergent manner into both the (2S,3R) and the (2R,3R) diastereomers of N-Boc-β-methylphenylalanine, syn-1 and anti-1, respectively. Activation of the secondary hydroxy group in anti-10 as a mesylate, followed by nucleophilic displacement with sodium azide, hydrogenolysis with simultaneous protection of the amino group, and saponification with LiOH, affords syn-1. The same reaction sequence applied to syn-10, obtained in turn by Mitsunobu reaction of anti-10 with p-nitrobenzoic acid followed by the hydrolysis of the resulting p-nitrobenzoate, leads to anti-1. Both products have been obtained with ≥99% enantiomeric excess.