(2R,3E,5S,6S,7S,8R)-5-acetoxy-6-acetoxymethyl-7-(3,4-dimethoxybenzyloxy)-2,4,8-trimethyl-3-nonene-1,9-diol

Base Information

Chemical Name:(2R,3E,5S,6S,7S,8R)-5-acetoxy-6-acetoxymethyl-7-(3,4-dimethoxybenzyloxy)-2,4,8-trimethyl-3-nonene-1,9-diol
CAS No.:240821-16-3
Molecular Formula:C₂₆H₄₀O₉
Molecular Weight:496.598
Hs Code.:

Synonyms:(2R,3E,5S,6S,7S,8R)-5-acetoxy-6-acetoxymethyl-7-(3,4-dimethoxybenzyloxy)-2,4,8-trimethyl-3-nonene-1,9-diol

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Chemical Property of (2R,3E,5S,6S,7S,8R)-5-acetoxy-6-acetoxymethyl-7-(3,4-dimethoxybenzyloxy)-2,4,8-trimethyl-3-nonene-1,9-diol

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Technology Process of (2R,3E,5S,6S,7S,8R)-5-acetoxy-6-acetoxymethyl-7-(3,4-dimethoxybenzyloxy)-2,4,8-trimethyl-3-nonene-1,9-diol

There total 25 articles about (2R,3E,5S,6S,7S,8R)-5-acetoxy-6-acetoxymethyl-7-(3,4-dimethoxybenzyloxy)-2,4,8-trimethyl-3-nonene-1,9-diol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

: 240821-14-1
Acetic acid (E)-(1S,4R)-1-[(1S,2S,3R)-1-acetoxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-2-(3,4-dimethoxy-benzyloxy)-3-methyl-butyl]-5-(tert-butyl-diphenyl-silanyloxy)-2,4-dimethyl-pent-2-enyl ester

: 240821-16-3
(2R,3E,5S,6S,7S,8R)-5-acetoxy-6-acetoxymethyl-7-(3,4-dimethoxybenzyloxy)-2,4,8-trimethyl-3-nonene-1,9-diol

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; Ambient temperature;
DOI:10.1055/s-1999-2730

Reference yield:

: (2R,3E,6S,7S,8R)-6-(tert-butyldimethylsilyloxymethyl)-1,9-di(tert-butyldiphenylsilyloxy)-7-(3,4-dimethoxybenzyloxy)-2,4,8-trimethyl-3-nonen-5-ol

: 240821-16-3
(2R,3E,5S,6S,7S,8R)-5-acetoxy-6-acetoxymethyl-7-(3,4-dimethoxybenzyloxy)-2,4,8-trimethyl-3-nonene-1,9-diol

Guidance literature:: Multi-step reaction with 5 steps

1: 91 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C

2: 99 percent / PPTS / ethanol / 6 h / 50 - 55 °C

3: 96 percent / Zn(BH₄)2 / diethyl ether / 7 h / 0 °C

4: 96 percent / Et₃N; DMAP / CH₂Cl₂ / 10.5 h / 0 °C

5: 100 percent / TBAF; AcOH / tetrahydrofuran / 144 h / 20 °C

With pyridine; dmap; zinc(II) tetrahydroborate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; Dess-Martin periodane; acetic acid; triethylamine; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; 1: Oxidation / 2: Hydrolysis / 3: Hydrogenolysis / 4: Acetylation / 5: desilylation;
DOI:10.1248/cpb.47.1288

Reference yield:

: 240821-06-1
(2R,3E,6S,7S,8R)-6-(tert-butyldimethylsilyloxymethyl)-1,9-di(tert-butyldiphenylsilyloxy)-7-(3,4-dimethoxybenzyloxy)-2,4,8-trimethyl-3-nonen-5-one

: 240821-16-3
(2R,3E,5S,6S,7S,8R)-5-acetoxy-6-acetoxymethyl-7-(3,4-dimethoxybenzyloxy)-2,4,8-trimethyl-3-nonene-1,9-diol

Guidance literature:: Multi-step reaction with 4 steps

1: 99 percent / PPTS / ethanol / 6 h / 50 - 55 °C

2: 96 percent / Zn(BH₄)2 / diethyl ether / 7 h / 0 °C

3: 96 percent / Et₃N; DMAP / CH₂Cl₂ / 10.5 h / 0 °C

4: 100 percent / TBAF; AcOH / tetrahydrofuran / 144 h / 20 °C

With dmap; zinc(II) tetrahydroborate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; acetic acid; triethylamine; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; 1: Hydrolysis / 2: Hydrogenolysis / 3: Acetylation / 4: desilylation;
DOI:10.1248/cpb.47.1288