62311-47-1

Usage

Uses

Used in Pharmaceutical Industry:
(2Z)-3-Methyl-4-(benzyloxy)-2-buten-1-ol is used as a reactant for the preparation of Methyl-D-erythritol Phosphate, which is essential in the biosynthesis of terpenoids. Terpenoids are a large and diverse class of organic compounds that have various applications in the pharmaceutical industry, including the development of drugs with diverse biological activities.
Used in Chemical Synthesis:
As a colorless oil, (2Z)-3-Methyl-4-(benzyloxy)-2-buten-1-ol can be utilized in various chemical synthesis processes, particularly in the production of complex organic molecules that require its specific structural features. Its versatility as a reactant makes it valuable in the development of new compounds for various applications.
Used in Research and Development:
(2Z)-3-Methyl-4-(benzyloxy)-2-buten-1-ol's role in terpenoid biosynthesis makes it an important molecule for research and development in the fields of biochemistry and molecular biology. Understanding its interactions and mechanisms can lead to the discovery of novel pathways and potential therapeutic targets.

Upstream product

• 22539-93-1 3-benzyloxypropanone 
• 449759-41-5 methyl (Z)-(3-methyl-4-benzyloxy)-2-buten-1-oate 

Downstream Products

• 449759-42-6 dibenzyl (Z)-(2-methyl-1-benzyloxy-2-buten-4-yl) phosphate 
• 960060-53-1 C₂₁H₂₂F₃NO₃ 

Relevant academic research and scientific papers

The asymmetric aza-claisen rearrangement: development of widely applicable pentaphenylferrocenyl palladacycle catalysts

Systematic studies have been performed to develop highly efficient catalysts for the asymmetric aza-Claisen rearrangement of trihaloacetimidates. Herein, we describe the stepwise development of these catalyst systems involving four different catalyst generations finally resulting in the development of a planar chiral pentaphenylferrocenyl oxazoline palladacycle. This complex is more reactive and has a broader substrate tolerance than all previously known catalyst systems for asymmetric aza-Claisen rearrange-ments. Our investigations also reveal that subtle changes can have a big impact on the activity. With the enhanced catalyst activity, the asymmetric aza-Claisen rearrangement has a very broad scope: the methodology not only allows the formation of highly enantioenriched primary allylic amines, but also secondary and tertiary amines; al-lylic amines with N-substituted quaternary stereocenters are conveniently accessible as well. The reaction conditions tolerate many important functional groups, thus providing stereoselective access to valuable functionalized building blocks, for example, for the synthesis of unnatural amino acids. Our results suggest that face-selective olefin coordination is the enantioselectivitydetermining step, which is almost exclusively controlled by the element of planar chirality.

Asymmetric formation of allylic amines with N-substituted quaternary stereocenters by PdII-catalyzed aza-Claisen rearrangements

(Chemical Equation Presented) With the ferrocene imidazoline palladacycle FIP-Cl as precatalyst, quaternary N-substituted stereocenters can be generated in an asymmetric aza-Claisen rearrangement. Excellent enantioselectivities are obtained even if R and R′ have a similar or identical size (see scheme: e.g. 96% ee for CH3/CD3).

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.