99528-64-0

Upstream product

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

Downstream Products

• 197714-17-3 methyl (2S,3R)-3-phenyl-2-[(p-nitrobenzoyl)oxy]butanoate 
• 197714-29-7 methyl (2R,3R)-2-[(tert-butoxycarbonyl)amino]-3-phenylbutanoate 
• 197714-18-4 methyl (2S,3R)-2-[(tert-butoxycarbonyl)amino]-3-phenylbutanoate 
• 197714-31-1 (2R,3R)-2-[(tert-butoxycarbonyl)amino]-3-phenylbutanol 
• 197714-07-1 methyl (2R,3R)-2-(methanesulfonyloxy)-3-phenylbutanoate 
• 197714-21-9 methyl (2S,3R)-2-(methanesulfonyloxy)-3-phenylbutanoate 
• 117486-31-4 (2S,3R)-2-Hydroxy-3-phenylbutyric acid methyl ester 
• 198493-85-5 (2R,3R)-2-[(tert-butoxycarbonyl)amino]-3-phenylbutanoic acid 
• 91828-71-6 (2R,3R)-2-Hydroxy-3-phenylbutyric acid methyl ester 
• 145432-51-5 (βR)-N-(tert-butoxycarbonyl)-β-methyl-L-phenylalanine 
• 212910-87-7 C₅₁H₅₃Cl₆NO₁₇ 
• 174729-13-6 C₄₄H₄₅Cl₆N₃O₁₆ 
• 114915-14-9 7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel 
• 114915-20-7 Docetaxel 

Relevant academic research and scientific papers

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.

Synthesis of taxoids 3. A novel and efficient method for preparation of taxoids by employing cis-glycidic acid

A novel route for the synthesis of docetaxel (2) using esterification of (2R,3R)-glycidic acid with 7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)-10- deacetylbaccatin III is described. Subsequent stereo- and regio-selective conversion afforded 2 and related novel compounds.

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.

Baccatin derivatives and processes for preparing the same

Disclosed are 13α-(3-substituted-2-hydroxypropionyloxy)baccatin compounds represented by the formula: STR1 wherein R1 represents a lower alkanoyl group or a protective group for hydroxy group; R2 represents a protective group for hyd