(1R)-1-[(1S,2R)-2-(tert-butyldimethylsilyloxy)-1-(methoxyethoxymethoxy)-2-phenylethyl]-but-3-enyl 3-phenylprop-2-enoate

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Chemical Name:(1R)-1-[(1S,2R)-2-(tert-butyldimethylsilyloxy)-1-(methoxyethoxymethoxy)-2-phenylethyl]-but-3-enyl 3-phenylprop-2-enoate
CAS No.:474958-77-5
Molecular Formula:C₃₁H₄₄O₆Si
Molecular Weight:540.772
Hs Code.:

Synonyms:(1R)-1-[(1S,2R)-2-(tert-butyldimethylsilyloxy)-1-(methoxyethoxymethoxy)-2-phenylethyl]-but-3-enyl 3-phenylprop-2-enoate

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Chemical Property of (1R)-1-[(1S,2R)-2-(tert-butyldimethylsilyloxy)-1-(methoxyethoxymethoxy)-2-phenylethyl]-but-3-enyl 3-phenylprop-2-enoate

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Technology Process of (1R)-1-[(1S,2R)-2-(tert-butyldimethylsilyloxy)-1-(methoxyethoxymethoxy)-2-phenylethyl]-but-3-enyl 3-phenylprop-2-enoate

There total 11 articles about (1R)-1-[(1S,2R)-2-(tert-butyldimethylsilyloxy)-1-(methoxyethoxymethoxy)-2-phenylethyl]-but-3-enyl 3-phenylprop-2-enoate 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: 63.0%

: (1R,2S)-1-(tert-butyldimethylsilyloxy)-2-(methoxyethoxymethoxy)-1-phenyl-hex-5-en-3-ol

: 102-92-1,17082-09-6
Cinnamoyl chloride

: 474958-77-5
(1R)-1-[(1S,2R)-2-(tert-butyldimethylsilyloxy)-1-(methoxyethoxymethoxy)-2-phenylethyl]-but-3-enyl 3-phenylprop-2-enoate

Guidance literature:: With pyridine; dmap; In dichloromethane; at 0 ℃; for 15h;
DOI:10.1021/jo0259358

Reference yield:

: 77120-79-7
1-<(2-methoxyethoxy)methoxy>-2-propene

: 474958-77-5
(1R)-1-[(1S,2R)-2-(tert-butyldimethylsilyloxy)-1-(methoxyethoxymethoxy)-2-phenylethyl]-but-3-enyl 3-phenylprop-2-enoate

Guidance literature:: Multi-step reaction with 9 steps

1.1: sec-BuLi / tetrahydrofuran / 1 h / -78 °C

1.2: BF₃*Et₂O / tetrahydrofuran / -100 °C

2.1: tetrahydrofuran / 2 h / -100 °C

3.1: 42.8 g / NaOH; H₂O₂ / tetrahydrofuran; H₂O / 10 h / 25 °C

4.1: 76 percent / PPh₃; DEAD / toluene / 3 h / -50 °C

5.1: 77.5 percent / NaOH / methanol; H₂O / 1 h / 20 °C

6.1: 86 percent / imidazole / dimethylformamide / 4 h / 20 °C

7.1: OsO₄; NMO / acetone; H₂O / 6 h / 0 °C

7.2: 60 percent / NaIO₄ / acetone; H₂O / 0.5 h / 20 °C

8.1: diethyl ether; pentane / 2 h / -100 °C

8.2: 76 percent / NaOH; H₂O₂ / diethyl ether; pentane; H₂O / 6 h / 20 °C

9.1: 63 percent / pyridine; DMAP / CH₂Cl₂ / 15 h / 0 °C

With pyridine; 1H-imidazole; dmap; sodium hydroxide; osmium(VIII) oxide; N-methyl-2-indolinone; dihydrogen peroxide; sec.-butyllithium; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; pentane;
DOI:10.1021/jo0259358

Reference yield:

: 100-52-7
benzaldehyde

: 474958-77-5
(1R)-1-[(1S,2R)-2-(tert-butyldimethylsilyloxy)-1-(methoxyethoxymethoxy)-2-phenylethyl]-but-3-enyl 3-phenylprop-2-enoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: tetrahydrofuran / 2 h / -100 °C

2.1: 42.8 g / NaOH; H₂O₂ / tetrahydrofuran; H₂O / 10 h / 25 °C

3.1: 76 percent / PPh₃; DEAD / toluene / 3 h / -50 °C

4.1: 77.5 percent / NaOH / methanol; H₂O / 1 h / 20 °C

5.1: 86 percent / imidazole / dimethylformamide / 4 h / 20 °C

6.1: OsO₄; NMO / acetone; H₂O / 6 h / 0 °C

6.2: 60 percent / NaIO₄ / acetone; H₂O / 0.5 h / 20 °C

7.1: diethyl ether; pentane / 2 h / -100 °C

7.2: 76 percent / NaOH; H₂O₂ / diethyl ether; pentane; H₂O / 6 h / 20 °C

8.1: 63 percent / pyridine; DMAP / CH₂Cl₂ / 15 h / 0 °C

With pyridine; 1H-imidazole; dmap; sodium hydroxide; osmium(VIII) oxide; N-methyl-2-indolinone; dihydrogen peroxide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; pentane;
DOI:10.1021/jo0259358