methyl 4,6-bis[(2-methoxyethoxy)methyloxy]-2-[(1'E,6'S,10'S)-6',10'-bis(tert-butyldimethylsilyloxy)undec-1'-en-1'-yl]benzoate

Base Information

Chemical Name:methyl 4,6-bis[(2-methoxyethoxy)methyloxy]-2-[(1'E,6'S,10'S)-6',10'-bis(tert-butyldimethylsilyloxy)undec-1'-en-1'-yl]benzoate
CAS No.:445380-30-3
Molecular Formula:C₃₉H₇₂O₁₀Si₂
Molecular Weight:757.166
Hs Code.:

Synonyms:methyl 4,6-bis[(2-methoxyethoxy)methyloxy]-2-[(1'E,6'S,10'S)-6',10'-bis(tert-butyldimethylsilyloxy)undec-1'-en-1'-yl]benzoate

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Chemical Property of methyl 4,6-bis[(2-methoxyethoxy)methyloxy]-2-[(1'E,6'S,10'S)-6',10'-bis(tert-butyldimethylsilyloxy)undec-1'-en-1'-yl]benzoate

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Technology Process of methyl 4,6-bis[(2-methoxyethoxy)methyloxy]-2-[(1'E,6'S,10'S)-6',10'-bis(tert-butyldimethylsilyloxy)undec-1'-en-1'-yl]benzoate

There total 7 articles about methyl 4,6-bis[(2-methoxyethoxy)methyloxy]-2-[(1'E,6'S,10'S)-6',10'-bis(tert-butyldimethylsilyloxy)undec-1'-en-1'-yl]benzoate 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:

: 132260-56-1
methyl 4,6-bis<<(2-methoxyethoxy)methyl>oxy>-2-iodobenzoate

: 311805-80-8
(5R,9S)-5,9-bis(tert-butyldimethylsilyloxy)decanal

: 445380-30-3
methyl 4,6-bis[(2-methoxyethoxy)methyloxy]-2-[(1'E,6'S,10'S)-6',10'-bis(tert-butyldimethylsilyloxy)undec-1'-en-1'-yl]benzoate

Guidance literature:: (5R,9S)-5,9-bis(tert-butyldimethylsilyloxy)decanal; Bu₃SnCHI₂; With chromium dichloride; In N,N-dimethyl-formamide; at 0 ℃;

methyl 4,6-bis<<(2-methoxyethoxy)methyl>oxy>-2-iodobenzoate; With trifuran-2-yl-phosphane; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In toluene; at 100 ℃; for 4h; Further stages.;
DOI:10.1039/b005942k

Reference yield:

: 132260-56-1
methyl 4,6-bis<<(2-methoxyethoxy)methyl>oxy>-2-iodobenzoate

: 311805-80-8
(5R,9S)-5,9-bis(tert-butyldimethylsilyloxy)decanal

: 213203-63-5
tri-n-butyl(diiodomethyl)stannane

: 445380-30-3
methyl 4,6-bis[(2-methoxyethoxy)methyloxy]-2-[(1'E,6'S,10'S)-6',10'-bis(tert-butyldimethylsilyloxy)undec-1'-en-1'-yl]benzoate

Guidance literature:: (5R,9S)-5,9-bis(tert-butyldimethylsilyloxy)decanal; tri-n-butyl(diiodomethyl)stannane; With chromium dichloride; In N,N-dimethyl-formamide; at 0 ℃; for 5h;

methyl 4,6-bis<<(2-methoxyethoxy)methyl>oxy>-2-iodobenzoate; With trifuran-2-yl-phosphane; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In toluene; at 80 ℃; for 4h; Further stages.;
DOI:10.1039/b201164f

Reference yield:

: 311805-64-8
(5S,9S)-5,9-bis(tert-butyldimethylsilyloxy)decan-1-ol

: 445380-30-3
methyl 4,6-bis[(2-methoxyethoxy)methyloxy]-2-[(1'E,6'S,10'S)-6',10'-bis(tert-butyldimethylsilyloxy)undec-1'-en-1'-yl]benzoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 80 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.5 h / -78 °C

2.1: CrCl₂ / dimethylformamide / 5 h / 0 °C

2.2: 290 mg / P(2-furyl)3 / Pd₂(dba)3 / toluene / 4 h / 80 °C

With chromium dichloride; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; N,N-dimethyl-formamide; 1.1: Swern oxidation / 2.2: Stille coupling reaction;
DOI:10.1039/b201164f