162601-88-9

Upstream product

• 76530-42-2 (R)-4-ethynyl-3,5,5-trimethylcyclohex-3-enyl acetate 
• 81058-27-7 2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide 
• 521291-38-3 2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-2-[(S)-3-((R)-4-acetoxy-2,6,6-trimethyl-cyclohex-1-enyl)-1-methyl-prop-2-ynyloxy]-3,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-4-yl ester 
• 322474-87-3 4-({(4R)-4-[(1,1-dimethylethyl)dimethylsilyl]oxy}-2,6,6-trimethylcyclohex-1-enyl)but-3-yn-2-one 
• 322474-89-5 Acetic acid (R)-4-((S)-3-hydroxy-but-1-ynyl)-3,5,5-trimethyl-cyclohex-3-enyl ester 
• 322474-88-4 4-[(4R)-4-acetyloxy-2,6,6-trimethylcyclohex-1-enyl]but-3-yn-2-one 
• 224631-90-7 4-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-enyl]but-3-yn-2-one 
• 322474-86-2 1,1-dimethylethyl{[(1R)-4-ethynyl-3,5,5-trimethylcyclohex-3-entl]oxy}dimethylsilane 
• 118829-40-6 (R)-4-ethynyl-3,5,5-trimethylcyclohex-3-en-1-ol 

Relevant academic research and scientific papers

Identification of (3S, 9R)- and (3S, 9S)-megastigma-6,7-dien-3,5,9-triol 9-O-β-D-glucopyranosides as damascenone progenitors in the flowers of Rosa damascena Mill.

The progenitors of damascenone (1), the most intensive C 13-norisoprenoid volatile aroma constituent of rose essential oil, were surveyed in the flowers of Rosa damascena Mill. Besides 9-O-β-D-glucopyranosyl-3-hydroxy-7,8-didehydro-β-ionol (4b), a stable progenitor already isolated from the residual water after steam distillation of flowers of R. damascena Mill., two labile progenitors were identified to be (3S, 9R)- and (3S, 9S)-megastigma-6,7-dien-3,5,9-triol 9-O-β-D-glucopyranosides (2b) based on their synthesis and HPLC-MS analytical data. Compound 2b gave damascenone (1), 3-hydroxy-β-damascone (3) and 4b upon heating under acidic conditions.

Stereocontrolled synthesis of glucosidic damascenone precursors

A stereocontrolled synthesis of optically active β-D-glucopyranosides and glucosidic damascenone precursors was discussed. The method used was asymmetric transfer hydrogenation to α, β-acetylenic ketones catalyzed by chiral ruthenium complexes. To facilitate the confirmation of the stereochemistries of natural glucosides, separation of synthetic four isomers by HPCL was examined.

Stereocontrolled synthesis of optically active β-D-glucopyranosides of 3-hydroxy-7,8-didehydro-β-ionol

A stereocontrolled synthesis of optically active β-D-glucopyranosides 1-4 of 3-hydroxy-7,8-didehydro-β-ionol utilizing an asymmetric transfer hydrogenation to α,β-acetylenic ketones catalyzed by chiral ruthenium complexes as the key step is described.