449759-41-5

Basic information

• Product Name: (2Z)-3-Methyl-4-(benzyloxy)-2-butenoic Acid Methyl Ester
• Synonyms: (2Z)-3-Methyl-4-(benzyloxy)-2-butenoic Acid Methyl Ester;QHMCFYFWVUBHQT-FLIBITNWSA-N
• CAS NO: 449759-41-5
• Molecular Formula: C₁₃H₁₆O₃
• Molecular Weight: 220.26434
• Product Categories: Aliphatics, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 449759-41-5.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform
• CAS DataBase Reference: (2Z)-3-Methyl-4-(benzyloxy)-2-butenoic Acid Methyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2Z)-3-Methyl-4-(benzyloxy)-2-butenoic Acid Methyl Ester(449759-41-5)
• EPA Substance Registry System: (2Z)-3-Methyl-4-(benzyloxy)-2-butenoic Acid Methyl Ester(449759-41-5)

Safety Data

• Hazardous Substances Data: 449759-41-5(Hazardous Substances Data)

Usage

Chemical Properties

Colorless Oil

Uses

(2Z)-3-Methyl-4-(benzyloxy)-2-butenoic Acid Methyl Ester can be used as a reactant used in the preparation of Methyl-D-erythritol Phosphate, a substrate in terpenoid biosynthesis.

Upstream product

• 22539-93-1 3-benzyloxypropanone 

Downstream Products

• 62311-47-1 (Z)-4-(benzyloxy)-3-methylbut-2-en-1-ol 
• 449759-42-6 dibenzyl (Z)-(2-methyl-1-benzyloxy-2-buten-4-yl) phosphate 

Relevant articles and documents

Synthesis of 4-diphosphocytidyl-2-C-methyl-D-erythritol and 2-C-methyl-D-erythritol-4-phosphate.

2-C-Methyl-D-erythritol 4-phosphate (MEP, 2) and 4-diphosphocytidyl-2-C-methyl-D-erythritol (CDPME, 3) are metabolites in the MEP pathway for biosynthesis of isoprenoid compounds in bacteria, plant chloroplasts, and algae. The free phosphoacid of 2 was prepared from benzyloxyacetone in five steps with an overall yield of 27% and an enantiomeric ratio (er) of 75:25. Following titration to the corresponding tributylammonium salt, 2 was coupled to cytidine 5'-monophosphate using a protocol originally developed for synthesis of base-sensitive nucleoside diphosphate sugars to give 3 in 40% yield, following purification by size exclusion chromatography.