162601-88-9

Upstream product

• 76530-42-2 (R)-4-ethynyl-3,5,5-trimethylcyclohex-3-enyl acetate 
• 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 
• 118829-40-6 (R)-4-ethynyl-3,5,5-trimethylcyclohex-3-en-1-ol 
• 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 
• 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 

Relevant academic research and scientific papers

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.

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 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.