232280-22-7

Upstream product

• 72657-23-9 methyl (R)-3-hydroxy-2-methylpropionate 
• 80522-42-5 triisopropylsilyl trifluoromethanesulfonate 

Downstream Products

• 1320344-44-2 ({(2R)-2-(2S,5S,6S)-6-[(1S,2S,3S)-2-(benzyloxy)-4-(methoxymethoxy)-1,3-dimethylbutyl]-5-methyltetrahydro-2H-2-pyranylpropyl}oxy)(triisopropyl)silane 
• 1320344-52-2 (2R,3R,6S,7S,8R,9S,10S)-9-(benzyloxy)-11-(methoxymethoxy)-2,6,8,10-tetramethyl-1-[(1,1,1-triisopropylsilyl)oxy]undecan-3,7-diol 
• 1320344-51-1 (2R,3R,6S,7S,8R,9S,10S)-9-(benzyloxy)-7-[(4-methoxybenzyl)oxy]-11-(methoxymethoxy)-2,6,8,10-tetramethyl-1-[(1,1,1-triisopropylsilyl)oxy]-4-undecan-3-ol 
• 1320344-50-0 (2R,3R,4E,6S,7S,8R,9S,10S)-9-(benzyloxy)-7-[(4-methoxybenzyl)oxy]-11-(methoxymethoxy)-2,6,8,10-tetramethyl-1-[(1,1,1-triisopropylsilyl)oxy]-4-undecen-3-ol 
• 1320344-49-7 (2R,4E,6S,7S,8R,9S,10S)-9-(benzyloxy)-7-[(4-methoxybenzyl)oxy]-11-(methoxymethoxy)-2,6,8,10-tetramethyl-1-[(1,1,1-triisopropylsilyl)oxy]-4-undecen-3-one 
• 241155-48-6 (4R,5S)-4,5-Dimethyl-2-methylene-6-triisopropylsilanyloxy-hexanoic acid (E)-(2S,3R)-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-hepta-4,6-dienyl ester 
• 232280-20-5 (1R,6S)-2-O-acetyl-1,4-anhydro-3,5,6-trideoxy-1-{3-[(4-methoxybenzyl)oxy]propyl}-6-methyl-2-C-methyl-5-methylene-7-O-(triisopropylsilyl)-D-xylo-heptitol 
• 232280-19-2 (2R,3R)-1,2-O-isopropylidene-6-[(4-methoxybenzyl)oxy]-3-{(3S)-3-methyl-2-methylene-4-[(triisopropylsilyl)oxy]butoxy}hexane-1,2-diol 
• 232280-13-6 (1R,6S)-1,4-anhydro-3,5,6-trideoxy-1-{3-[(4-methoxybenzyl)oxy]propyl}-6-methyl-2-C-methyl-5-methylene-7-O-(triisopropylsilyl)-D-xylo-heptitol 
• 232280-12-5 (3R)-1-diazo-6-[(4-methoxybenzyl)oxy]-2-{(3S)-3-methyl-2-methylene-4-[(triisopropylsilyl)oxy]butoxy}hexan-2-one 
• 232280-11-4 (2R)-5-[(4-methoxybenzyl)oxy]-2-{(3S)-3-methyl-2-methylene-4-[(triisopropylsilyl)oxy]butoxy}pentanal 
• 256643-35-3 (2R,3R,4S,5S,6R,7S,8R)-5-benzoyloxy-1-benzyloxy-7-tert-butyldimethylsilyloxy-2,4,6,8-tetramethyl-9-(triisopropylsilyloxy)-3-nonanol 
• 256643-36-4 (2R,3R,4S,5S,6R,7S,8R)-1-benzyloxy-7-tert-butyldimethylsilyloxy-2,4,6,8-tetramethyl-9-(triisopropylsilyloxy)-3,5-nonanediol 
• 256643-34-2 (2R,4R,5R,6R,7S,8R)-1-benzyloxy-7-tert-butyldimethylsilyloxy-5-hydroxy-2,4,6,8-tetramethyl-9-(triisopropylsilyloxy)-3-nonanone 

Relevant academic research and scientific papers

Syntheses of Gymnothespirolignans B and C and Non-natural Isomer 9-Epi-gymnothespirolignan B

Syntheses of polycyclic spiro lignans gymnothespirolignans B and C as well as the unnatural isomer 9-epi-gymnothespirolignan B were accomplished using (R)-Roche ester and an appropriately substituted fluorenone. Key features of the convergent syntheses include coupling of the fluorenone and an iodo-alkene intermediate derived from (R)-Roche ester in the presence of the Lewis acid TiCl(OiPr)3, C9-O bond formation via an SN2 reaction with retention of stereochemistry, and diastereoselective hydrogenations of a common alkene intermediate guided by accessibility or positioning by the C8-methoxy.

Toward a total synthesis of brassinosteroids; structure assessment of the Ireland-Claisen products of geranyl and neryl esters

As estimated by 1H NMR analysis, thermal isomerisation of the kinetic silylenolate derived from the ester (Z)-8a proceeds with acceptable diastereo and facial selectivity, thence affording an acid having the required absolute configuration for further elaboration to brassinosteroids.