(-)-(2S,5S)-2-[(tert-butyldimethylsilanyloxy)-(3,4-dimethoxyphenyl)methyl]but-3-en-1-ol

Base Information

Chemical Name:(-)-(2S,5S)-2-[(tert-butyldimethylsilanyloxy)-(3,4-dimethoxyphenyl)methyl]but-3-en-1-ol
CAS No.:689277-88-1
Molecular Formula:C₁₉H₃₂O₄Si
Molecular Weight:352.546
Hs Code.:

Synonyms:(-)-(2S,5S)-2-[(tert-butyldimethylsilanyloxy)-(3,4-dimethoxyphenyl)methyl]but-3-en-1-ol

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Chemical Property of (-)-(2S,5S)-2-[(tert-butyldimethylsilanyloxy)-(3,4-dimethoxyphenyl)methyl]but-3-en-1-ol

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Technology Process of (-)-(2S,5S)-2-[(tert-butyldimethylsilanyloxy)-(3,4-dimethoxyphenyl)methyl]but-3-en-1-ol

There total 4 articles about (-)-(2S,5S)-2-[(tert-butyldimethylsilanyloxy)-(3,4-dimethoxyphenyl)methyl]but-3-en-1-ol 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: 85.0%

: 689277-87-0
(+)-(2S,5S)-4-benzyl-3-{2-[(tert-butyldimethylsilanyloxy)-(3,4-dimethoxyphenyl)methyl]but-3-enoyl}oxazolidin-2-one

: 689277-88-1
(-)-(2S,5S)-2-[(tert-butyldimethylsilanyloxy)-(3,4-dimethoxyphenyl)methyl]but-3-en-1-ol

Guidance literature:: With sodium tetrahydroborate; In tetrahydrofuran; water; at 25 ℃; for 16h;
DOI:10.1021/ol049878b

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 689277-88-1
(-)-(2S,5S)-2-[(tert-butyldimethylsilanyloxy)-(3,4-dimethoxyphenyl)methyl]but-3-en-1-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 1.45 g / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

2: 85 percent / NaBH₄ / tetrahydrofuran; H₂O / 16 h / 25 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/ol049878b

Reference yield:

: 120-14-9
3,4-dimethoxy-benzaldehyde

: 689277-88-1
(-)-(2S,5S)-2-[(tert-butyldimethylsilanyloxy)-(3,4-dimethoxyphenyl)methyl]but-3-en-1-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: (n-Bu)2BOTf; Et₃N / CH₂Cl₂ / 1.33 h / -78 - 0 °C

1.2: CH₂Cl₂ / 2 h / -78 - 0 °C

1.3: H₂O₂ / CH₂Cl₂; aq. phosphate buffer / 20 °C / pH 7.2

2.1: 1.45 g / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

3.1: 85 percent / NaBH₄ / tetrahydrofuran; H₂O / 16 h / 25 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; di-n-butylboryl trifluoromethanesulfonate; triethylamine; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/ol049878b