ethyl 2-[(3R,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]cyclohexylidene]acetate

Base Information

• Chemical Name: ethyl 2-[(3R,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]cyclohexylidene]acetate
• CAS No.: 139356-36-8
• Molecular Formula: C22H44O4Si2
• Molecular Weight: 428.76
• European Community (EC) Number: 866-421-4
• DSSTox Substance ID: DTXSID70431362
• Nikkaji Number: J1.630.548K
• Mol file: 139356-36-8.mol

Synonyms:139356-36-8;ethyl 2-[(3R,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]cyclohexylidene]acetate;DTXSID70431362;VKHVAGVBCANCSM-RTBURBONSA-N;Ethyl 2-((3R,5R)-3,5-bis((tert-butyldimethylsilyl)oxy)cyclohexylidene)acetate;[(3R)-3beta,5alpha-Bis(tert-butyldimethylsiloxy)cyclohexane-1-ylidene]acetic acid ethyl ester;trans-[3,5-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]cyclohexylidene]-acetic acid ethyl ester

Chemical Property of ethyl 2-[(3R,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]cyclohexylidene]acetate

Chemical Property:

• PSA: 44.76000
• LogP: 6.44060
• Solubility.: CDCl3, CD3OD
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 9
• Exact Mass: 428.27781295
• Heavy Atom Count: 28
• Complexity: 530

Purity/Quality:

(3R-trans)-[3,5-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]cyclohexylidene]-aceticAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C=C1CC(CC(C1)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C
• Isomeric SMILES: CCOC(=O)C=C1C[C@H](C[C@@H](C1)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C
• Uses: (3R-trans)-[3,5-Bis[[(1,1-diMethylethyl)diMethylsilyl]oxy]cyclohexylidene]-acetic Acid Ethyl Ester is used in the preparation of Vitamin D compounds.

Technology Process of ethyl 2-[(3R,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]cyclohexylidene]acetate

There total 13 articles about ethyl 2-[(3R,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]cyclohexylidene]acetate 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: 86.0%

trimethylsilanyl-acetic acid ethyl ester (4071-88-9) + 3,5-di-(tert-butyl-dimethylsilyloxy)-(3S,5S)-cyclohexan-1-one (139356-35-7) → [(3R,5R)-3,5-bis-(tert-butyldimethylsilyloxy)cyclohexylidene]acetic acid ethyl ester (139356-36-8)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 2h;

DOI:10.1016/0040-4039(91)80559-O

Reference yield: 71.0%

3,5-di-(tert-butyl-dimethylsilyloxy)-(3S,5S)-cyclohexan-1-one (139356-35-7) → [(3R,5R)-3,5-bis-(tert-butyldimethylsilyloxy)cyclohexylidene]acetic acid ethyl ester (139356-36-8)

Guidance literature:

trimethylsilanyl-acetic acid ethyl ester; With n-butyllithium; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at -78 - 0 ℃; for 0.5h;

3,5-di-(tert-butyl-dimethylsilyloxy)-(3S,5S)-cyclohexan-1-one; In tetrahydrofuran; at -78 ℃; for 3.5h;

Reference yield:

(1S,4S,6S)-4-(tert-butyldimethylsilyloxy)-7-oxa-bicyclo[4.1.0]heptan-2-one → [(3R,5R)-3,5-bis-(tert-butyldimethylsilyloxy)cyclohexylidene]acetic acid ethyl ester (139356-36-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / NaH / tetrahydrofuran / 1 h / 0 °C

2: HCO₂H; Et₃N; Bu₃P / Pd₂(dba)3(CHCl₃) / dioxane / 0.5 h / 20 °C

3: 1.92 g / imidazole / dimethylformamide / 12 h / 20 °C

With 1H-imidazole; formic acid; tributylphosphine; sodium hydride; triethylamine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide; 1: Horner-Wadsworth-Emmons olefination;

DOI:10.1021/ol016052q

upstream raw materials:

trimethylsilanyl-acetic acid ethyl ester

3,5-di-(tert-butyl-dimethylsilyloxy)-(3S,5S)-cyclohexan-1-one

methyl quinicate

methanol

Downstream raw materials:

[(3R,5R)-3,5-bis-(tert-butyldimethylsilanyloxy)cyclohexylidene]-ethanol

(S)-2-((1R,3aS,7aR,E)-4-(2-((3R,5R)-3,5-bis(tertbutyldimethylsilyloxy)cyclohexylidene)ethylidene)-7a-methyloctahydro-1H-inden-1-yl)propanal

((1R,3R)-5-((E)-2-((1R,3aS,7aR)-1-((S)-1,1-dimethoxypropan-2-yl)-7a-methyldihydro-1H-inden-4(2H,5H,6H,7H,7aH)-ylidene)ethylidene)cyclohexane-1,3-diyl)bis(oxy)bis(tertbutyldimethylsilane)

(1R,7aR)-4-[2-[(3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-eth-(E)-ylidene]-1-((R)-1,5-dimethyl-5-trimethylsilanyloxy-hexyl)-7a-methyl-octahydro-indene

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