(1S,5S,8aR)-5-(3-Benzyloxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-1,5-dimethyl-2-methylene-1,2,3,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid ethyl ester

Base Information

Chemical Name:(1S,5S,8aR)-5-(3-Benzyloxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-1,5-dimethyl-2-methylene-1,2,3,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid ethyl ester
CAS No.:352695-11-5
Molecular Formula:C₃₂H₅₀O₄Si
Molecular Weight:526.832
Hs Code.:

(1S,5S,8aR)-5-(3-Benzyloxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-1,5-dimethyl-2-methylene-1,2,3,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid ethyl ester

Synonyms:(1S,5S,8aR)-5-(3-Benzyloxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-1,5-dimethyl-2-methylene-1,2,3,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid ethyl ester

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Chemical Property of (1S,5S,8aR)-5-(3-Benzyloxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-1,5-dimethyl-2-methylene-1,2,3,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid ethyl ester

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Technology Process of (1S,5S,8aR)-5-(3-Benzyloxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-1,5-dimethyl-2-methylene-1,2,3,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid ethyl ester

There total 12 articles about (1S,5S,8aR)-5-(3-Benzyloxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-1,5-dimethyl-2-methylene-1,2,3,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid ethyl ester 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: 30.0%

: 5717-41-9
ethyl 2-methylbuta-2,3-dienoate

: 352695-10-4
{1-[6-(3-benzyloxy-propyl)-6-methyl-cyclohex-1-enyl]-vinyloxy}-tert-butyl-dimethyl-silane

: (1S,5S)-5-(3-Benzyloxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-1,5-dimethyl-2-methylene-1,2,3,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid ethyl ester

: (1R,5S)-5-(3-Benzyloxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-1,5-dimethyl-2-methylene-1,2,3,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid ethyl ester

: 352695-11-5
(1S,5S,8aR)-5-(3-Benzyloxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-1,5-dimethyl-2-methylene-1,2,3,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid ethyl ester

: (1R,5S,8aR)-5-(3-Benzyloxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-1,5-dimethyl-2-methylene-1,2,3,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid ethyl ester

Guidance literature:: In toluene; at 140 ℃; for 168h; Further byproducts given;
DOI:10.1021/ol016073k

Reference yield: 14.0%

: 5717-41-9
ethyl 2-methylbuta-2,3-dienoate

: 352695-10-4
{1-[6-(3-benzyloxy-propyl)-6-methyl-cyclohex-1-enyl]-vinyloxy}-tert-butyl-dimethyl-silane

: 5-(3-benzyloxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-1,2,5-trimethyl-1,5,6,7,8,8a-hexahydro-naphthalene-1-carboxylic acid ethyl ester

: 2-[3-[6-(3-benzyloxy-propyl)-6-methyl-cyclohex-1-enyl]-3-(tert-butyl-dimethyl-silanyloxy)-cyclobutylidene]-propionic acid ethyl ester

: (1R,5S)-5-(3-Benzyloxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-1,5-dimethyl-2-methylene-1,2,3,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid ethyl ester

: 352695-11-5
(1S,5S,8aR)-5-(3-Benzyloxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-1,5-dimethyl-2-methylene-1,2,3,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid ethyl ester

Guidance literature:: In toluene; at 140 ℃; for 168h; Further byproducts given;
DOI:10.1021/ol016073k

Reference yield:

: 100-39-0
benzyl bromide

: 352695-11-5
(1S,5S,8aR)-5-(3-Benzyloxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-1,5-dimethyl-2-methylene-1,2,3,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 82 percent / NaH / tetrahydrofuran / 5 h / 22 °C

2.1: 92 percent / (COCl)2; DMSO; triethylamine / CH₂Cl₂ / 0.75 h / -78 °C

3.1: LDA / tetrahydrofuran; various solvent(s) / 2 h / -78 °C

3.2: 84 percent / tetrahydrofuran; various solvent(s) / 0 - 22 °C

4.1: 96 percent / CuI; BuNH₂ / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / tetrahydrofuran / 3 h / 22 °C

5.1: 100 percent / aq.KOH / methanol / 4 h / 22 °C

6.1: 75 percent / AcOH; Hg(OAc)2; sulfuric acid / 1.33 h / 22 °C

7.1: 99 percent / Et₃N / tetrahydrofuran / 1.5 h / 0 - 22 °C

8.1: 29 percent / toluene / 216 h / Heating

With potassium hydroxide; copper(l) iodide; oxalyl dichloride; sulfuric acid; mercury(II) diacetate; sodium hydride; acetic acid; dimethyl sulfoxide; N-butylamine; triethylamine; lithium diisopropyl amide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; toluene; 2.1: Swern oxidation / 4.1: Sonogashira coupling reaction;
DOI:10.1021/ol016073k