2,5,5-trimethyl-2-<2'-((1''S)-2''-formyl-6''(R)-methylcyclohex-2''-enyl)ethyl>-1,3-dioxane

Base Information

• Chemical Name: 2,5,5-trimethyl-2-<2'-((1''S)-2''-formyl-6''(R)-methylcyclohex-2''-enyl)ethyl>-1,3-dioxane
• CAS No.: 116399-90-7
• Molecular Formula: C₁₇H₂₈O₃
• Molecular Weight: 280.408
• Mol file: 116399-90-7.mol

Synonyms:2,5,5-trimethyl-2-<2'-((1''S)-2''-formyl-6''(R)-methylcyclohex-2''-enyl)ethyl>-1,3-dioxane

Chemical Property of 2,5,5-trimethyl-2-<2'-((1''S)-2''-formyl-6''(R)-methylcyclohex-2''-enyl)ethyl>-1,3-dioxane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2,5,5-trimethyl-2-<2'-((1''S)-2''-formyl-6''(R)-methylcyclohex-2''-enyl)ethyl>-1,3-dioxane

There total 6 articles about 2,5,5-trimethyl-2-<2'-((1''S)-2''-formyl-6''(R)-methylcyclohex-2''-enyl)ethyl>-1,3-dioxane 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:

2,5,5-trimethyl-2-<2'-(1''(R)-methyl-3''-oxocyclohex-2''-yl)ethyl>-1,3-dioxane p-tosylhydrazone (116400-00-1,138284-28-3,138284-30-7) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 2,5,5-trimethyl-2-<2'-((1''S)-2''-formyl-6''(R)-methylcyclohex-2''-enyl)ethyl>-1,3-dioxane (116399-90-7)

Guidance literature:

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; Yield given. Multistep reaction; 1.) hexane, RT, 90 min, 2.) hexane, 0 deg, 30 min;

DOI:10.1021/ja00029a028

Reference yield:

2,5,5-trimethyl-2-<2'-(1''(R)-methyl-3''-oxocyclohex-2''-yl)ethyl>-1,3-dioxane (116399-89-4) → 2,5,5-trimethyl-2-<2'-((1''S)-2''-formyl-6''(R)-methylcyclohex-2''-enyl)ethyl>-1,3-dioxane (116399-90-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / pyridine / tetrahydrofuran / Heating

2: 1.) n-BuLi, TMEDA, 2.) DMF

With pyridine; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; N,N-dimethyl-formamide; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)96582-1

Reference yield:

2-(2,5,5-trimethyl-1,3-dioxan-2-yl)ethyl bromide (87842-52-2) → 2,5,5-trimethyl-2-<2'-((1''S)-2''-formyl-6''(R)-methylcyclohex-2''-enyl)ethyl>-1,3-dioxane (116399-90-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) LDA, HMPA / 1.) THF, -78 deg C

2: Al(Hg) / tetrahydrofuran; H₂O

3: 94 percent / pyridine / tetrahydrofuran / Heating

4: 1.) n-BuLi, TMEDA, 2.) DMF

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; aluminum amalgam; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; N,N-dimethyl-formamide; lithium diisopropyl amide; In tetrahydrofuran; water;

DOI:10.1016/S0040-4039(00)96582-1

upstream raw materials:

2,5,5-trimethyl-2-<2'-(1''(R)-methyl-3''-oxocyclohex-2''-yl)ethyl>-1,3-dioxane p-tosylhydrazone

N,N-dimethyl-formamide

2,5,5-trimethyl-2-<2'-(1''(R)-methyl-3''-oxocyclohex-2''-yl)ethyl>-1,3-dioxane

2-(2,5,5-trimethyl-1,3-dioxan-2-yl)ethyl bromide

Downstream raw materials:

2,5,5-trimethyl-2-<2'-<4''-(1(S)-carboxyethyl)-1''(R)-methyl-3''-<(trimethylsilyl)methylene>cyclohex-2''-yl>ethyl>-1,3-dioxane

(S)-2-{(1S,3S,4R)-4-Methyl-3-(3-oxo-butyl)-2-[1-trimethylsilanyl-meth-(E)-ylidene]-cyclohexyl}-propionic acid

(+)-9-isoartemisinin

2-{(1S,3S,4R)-4-Methyl-3-[2-(2,5,5-trimethyl-[1,3]dioxan-2-yl)-ethyl]-2-[1-trimethylsilanyl-meth-(E)-ylidene]-cyclohexyl}-propionic acid methyl ester