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

Base Information

• Chemical Name: 2,5,5-trimethyl-2-<2'-<4''-(1(S)-carboxyethyl)-1''(R)-methyl-3''-<(trimethylsilyl)methylene>cyclohex-2''-yl>ethyl>-1,3-dioxane
• CAS No.: 116400-02-3
• Molecular Formula: C₂₃H₄₂O₄Si
• Molecular Weight: 410.67
• Mol file: 116400-02-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about 2,5,5-trimethyl-2-<2'-<4''-(1(S)-carboxyethyl)-1''(R)-methyl-3''-<(trimethylsilyl)methylene>cyclohex-2''-yl>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''S)-2''-formyl-6''(R)-methylcyclohex-2''-enyl)ethyl>-1,3-dioxane (116399-90-7) → 2,5,5-trimethyl-2-<2'-<4''-(1(S)-carboxyethyl)-1''(R)-methyl-3''-<(trimethylsilyl)methylene>cyclohex-2''-yl>ethyl>-1,3-dioxane (116400-02-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 2.) 4-(dimethylamino)pyridine (DMAP) / 1.) Et₂O, pentane, -78 deg C, 10 min, 2.) Et₂O, pentane, RT, 16 h

2: 63 percent / Et₂NH, n-BuLi / tetrahydrofuran; hexane / 1.) -78 deg C, 4 h, 2.) RT, 4 d

3: 1.) LDA / 1.) THF, hexane, from -78 to 50 deg C, 2.5 h, 2.) THF, hexane, RT, 1 h

With dmap; n-butyllithium; diethylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane;

DOI:10.1021/ja00029a028

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) → 2,5,5-trimethyl-2-<2'-<4''-(1(S)-carboxyethyl)-1''(R)-methyl-3''-<(trimethylsilyl)methylene>cyclohex-2''-yl>ethyl>-1,3-dioxane (116400-02-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) n-BuLi, TMEDA / 1.) hexane, RT, 90 min, 2.) hexane, 0 deg, 30 min

2: 2.) 4-(dimethylamino)pyridine (DMAP) / 1.) Et₂O, pentane, -78 deg C, 10 min, 2.) Et₂O, pentane, RT, 16 h

3: 63 percent / Et₂NH, n-BuLi / tetrahydrofuran; hexane / 1.) -78 deg C, 4 h, 2.) RT, 4 d

4: 1.) LDA / 1.) THF, hexane, from -78 to 50 deg C, 2.5 h, 2.) THF, hexane, RT, 1 h

With dmap; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; diethylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane;

DOI:10.1021/ja00029a028

Reference yield:

2,5,5-trimethyl-2-<2'-<1''R-methyl-3''-<(trimethylsilyl)hydroxymethyl>cyclohex-3''-en-2''-yl>ethyl>-1,3-dioxane acetyl ester (116399-91-8) → 2,5,5-trimethyl-2-<2'-<4''-(1(S)-carboxyethyl)-1''(R)-methyl-3''-<(trimethylsilyl)methylene>cyclohex-2''-yl>ethyl>-1,3-dioxane (116400-02-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 63 percent / Et₂NH, n-BuLi / tetrahydrofuran; hexane / 1.) -78 deg C, 4 h, 2.) RT, 4 d

2: 1.) LDA / 1.) THF, hexane, from -78 to 50 deg C, 2.5 h, 2.) THF, hexane, RT, 1 h

With n-butyllithium; diethylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane;

DOI:10.1021/ja00029a028

upstream raw materials:

2,5,5-trimethyl-2-<2'-<1''R-methyl-3''-<(trimethylsilyl)hydroxymethyl>cyclohex-3''-en-2''-yl>ethyl>-1,3-dioxane acetyl ester

methyl iodide

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

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

Downstream raw materials:

C₁₂H₁₃O₂(CH₃)3(O)(OO)

2-deoxyartemisinin

(2R,1'S,3'S,4'S)-2-<4'-methyl-3'-(3''-oxobutyl)-2'(E)-<(trimethylsilyl)methylene>cyclohexyl>propionic acid