4688-38-4

Usage

Uses

Used in Pharmaceutical Industry:
(3R,4S)-4,5-ISOPROPYLIDENE-PENT-2-YN-3-OL is used as a starting material for the synthesis of various pharmaceuticals and fine chemicals due to its unique chemical structure and reactivity.
Used in Organic Synthesis:
(3R,4S)-4,5-ISOPROPYLIDENE-PENT-2-YN-3-OL is used as a building block in the synthesis of other organic compounds, contributing to the development of new chemical entities.
Used in Material Science and Nanotechnology:
(3R,4S)-4,5-ISOPROPYLIDENE-PENT-2-YN-3-OL has potential applications in the field of material science and nanotechnology, where its unique properties can be utilized for the development of advanced materials and nanostructures.

InChI:InChI=1/C8H12O3/c1-4-6(9)7-5-10-8(2,3)11-7/h1,6-7,9H,5H2,2-3H3/t6-,7+/m0/s1

Upstream product

• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 70277-75-7 lithium acetylide 

Downstream Products

• 18524-19-1 (S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-prop-2-en-1-ol 
• 208114-17-4 (1S,5'R)-1-(2',2'-dimethyl-[1',3']dioxolan-4-yl)-3-phenyl-prop-2-yn-ol 
• 208048-44-6 cis-(1S,5'R)-1-diazoacetic acid 1-(2',2'-dimethyl-[1',3']dioxolane-4'-yl)-3-phenyl-prop-2-enyl ester 
• 208048-43-5 trans-(1S,5'R)-1-diazoacetic acid 1-(2',2'-dimethyl-[1',3']dioxolane-4'-yl)-3-phenyl-prop-2-enyl ester 
• 208048-46-8 cis-(1R,5'R)-1-diazoacetic acid 1-(2',2'-dimethyl-[1',3']dioxolane-4'-yl)-3-phenyl-prop-2-enyl ester 
• 208048-45-7 trans-(1R,5'R)-1-diazoacetic acid 1-(2',2'-dimethyl-[1',3']dioxolane-4'-yl)-3-phenyl-prop-2-enyl ester 

Relevant academic research and scientific papers

Synthesis of optically active β,γ-unsaturated α-amino acids of α,β-unsaturated γ-amino acids. S(N)2- vs. S(N)2'-dichotomy of the Mitsunobu amination of allylic alcohols

Novel and efficient syntheses (6-9 steps, overall yields 10-30%) are described for optically pure β,γ-unsaturated α-amino acids and α,β-unsaturated γ-amino acids, starting from (R)-isopropylidene glyceraldehyde and ethyl (S)-lactate, respectively. The key step is the Mitsunobu reaction of chiral secondary allylic alcohols with phthalimide as the nucleophile, where α,γ allylic transpositions are observed for the first time. The structure-α,γ-ratio-relationship is studied and also the stereochemistry of the allylic transposition. The α-substitution proceeds via clean S(N)2 inversion, whereas the γ-substitution corresponds to an (E)-anti attack of the nucleophilic with varying stereoselectivities.