124605-43-2

Basic information

• Product Name: (2S,3R)-(-)-methyl 3-hydroxy-3-phenyl-2-((p-tolylsulfonyl)oxy)propionate
• Synonyms: (2S,3R)-(-)-methyl 3-hydroxy-3-phenyl-2-((p-tolylsulfonyl)oxy)propionate
• CAS NO: 124605-43-2
• Molecular Weight: 350.392
• Mol File: 124605-43-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (2S,3R)-(-)-methyl 3-hydroxy-3-phenyl-2-((p-tolylsulfonyl)oxy)propionate(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R)-(-)-methyl 3-hydroxy-3-phenyl-2-((p-tolylsulfonyl)oxy)propionate(124605-43-2)
• EPA Substance Registry System: (2S,3R)-(-)-methyl 3-hydroxy-3-phenyl-2-((p-tolylsulfonyl)oxy)propionate(124605-43-2)

Safety Data

• Hazardous Substances Data: 124605-43-2(Hazardous Substances Data)

Upstream product

• 124649-67-8 methyl (2S,3R)-3-phenyl-2,3-dihydroxypropanoate 
• 98-59-9 p-toluenesulfonyl chloride 
• 103-26-4 Methyl cinnamate 

Downstream Products

• 124605-42-1 methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionate 
• 32981-85-4 methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate 
• 99458-15-8 Methyl (2R,3S)-(+)-2-hydroxy-3-azido-3-phenyl-propionate 
• 212910-87-7 C₅₁H₅₃Cl₆NO₁₇ 
• 174729-13-6 C₄₄H₄₅Cl₆N₃O₁₆ 
• 174729-12-5 13-O-((2R,3R)-3-phenylglycidoyl)-7,10-O,O'-bis(2,2,2-trichloroethoxycarbonyl)-10-deacetylbaccatin 
• 99528-64-0 cis-2,3-epoxy-3-phenyl-1-propanoic acid 
• 114915-14-9 7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel 
• 114915-20-7 Docetaxel 
• 99528-65-1 (2R,3R)-(+)-methyl 3-phenyloxiranecarboxylate 

Relevant articles and documents

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.

Selective Transformations of threo-2,3-Dihydroxy Esters

Two highly regio- and stereoselective transformations of threo-2,3-dihydroxy esters have been developed.In the first reaction, the α-hydroxy group is converted into a sulfonate group (tosylate or nosylate); the α-tosylates and α-nosylates are then subjected to basic conditions (K2CO3/ROH) to give erythro glycidic esters in high yield.The α-nosylates are also suitable electrophiles for azides, giving access to erythro-α-azido-β-hydroxy esters.The second reaction involves conversion of the diol esters to acetoxy bromo esters.The β-subsituent plays a key role in determining the regiochemistry since cases with β-alkyl substituents afford β-acetoxy-α-bromo esters exclusively, whereas a β-phenyl substitutent directs formation of the α-acetoxy-β-bromo ester.The acetoxy bromo esters can subsequently be converted to the threo glycidic esters (via the bromohydrin esters); selective hydrogenolysis of the bromine substituent can also be achieved.