(1S,2R)-1-{2-[(4-methoxyphenyl)methoxy]ethyl}-2-methylbut-3-enyl (2S)-4-methyl-2-(1,1,2,2-tetramethyl-1-silapropoxy)pentanoate

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Chemical Name:(1S,2R)-1-{2-[(4-methoxyphenyl)methoxy]ethyl}-2-methylbut-3-enyl (2S)-4-methyl-2-(1,1,2,2-tetramethyl-1-silapropoxy)pentanoate
CAS No.:350245-11-3
Molecular Formula:C₂₇H₄₆O₅Si
Molecular Weight:478.745
Hs Code.:

Synonyms:(1S,2R)-1-{2-[(4-methoxyphenyl)methoxy]ethyl}-2-methylbut-3-enyl (2S)-4-methyl-2-(1,1,2,2-tetramethyl-1-silapropoxy)pentanoate

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Chemical Property of (1S,2R)-1-{2-[(4-methoxyphenyl)methoxy]ethyl}-2-methylbut-3-enyl (2S)-4-methyl-2-(1,1,2,2-tetramethyl-1-silapropoxy)pentanoate

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Technology Process of (1S,2R)-1-{2-[(4-methoxyphenyl)methoxy]ethyl}-2-methylbut-3-enyl (2S)-4-methyl-2-(1,1,2,2-tetramethyl-1-silapropoxy)pentanoate

There total 2 articles about (1S,2R)-1-{2-[(4-methoxyphenyl)methoxy]ethyl}-2-methylbut-3-enyl (2S)-4-methyl-2-(1,1,2,2-tetramethyl-1-silapropoxy)pentanoate 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: 78.0%

: 220249-55-8
(3S,4R)-1-(4-methoxybenzyloxy)-4-(trifluoromethyl)hex-5-en-3-ol

: 350245-09-9
2-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentanoyl chloride

: 350245-11-3
(1S,2R)-1-{2-[(4-methoxyphenyl)methoxy]ethyl}-2-methylbut-3-enyl (2S)-4-methyl-2-(1,1,2,2-tetramethyl-1-silapropoxy)pentanoate

Guidance literature:: With dmap; TEA; In dichloromethane; at 0 ℃; for 0.75h;
DOI:10.1021/ol010044s

Reference yield:

: (tert-butyldimethylsilyl)oxy (2S)-4-methyl-2-[(tert-butyldimethylsilyl)oxy]pentanoate

: 350245-11-3
(1S,2R)-1-{2-[(4-methoxyphenyl)methoxy]ethyl}-2-methylbut-3-enyl (2S)-4-methyl-2-(1,1,2,2-tetramethyl-1-silapropoxy)pentanoate

Guidance literature:: Multi-step reaction with 2 steps

1: oxalyl chloride; DMF / CH₂Cl₂ / 4.5 h / 20 °C

2: 2.22 g / DMAP; Et₃N / CH₂Cl₂ / 0.75 h / 0 °C

With dmap; oxalyl dichloride; triethylamine; N,N-dimethyl-formamide; In dichloromethane;
DOI:10.1021/jo0302197

Reference yield:

: 350245-11-3
(1S,2R)-1-{2-[(4-methoxyphenyl)methoxy]ethyl}-2-methylbut-3-enyl (2S)-4-methyl-2-(1,1,2,2-tetramethyl-1-silapropoxy)pentanoate

: 162473-78-1
desepoxyarenastatin A

Guidance literature:: Multi-step reaction with 7 steps

1.1: DDQ / CH₂Cl₂; H₂O / 2 h / 0 - 20 °C

1.2: 76 mg / Dess-Martin periodinane / CH₂Cl₂ / 2 h

2.1: 94 percent / CH₂Cl₂ / 2 h / 0 - 20 °C

3.1: 83 percent / TFA / CH₂Cl₂ / 8 h / 0 - 20 °C

4.1: 64 percent / DIEA; HBTU / acetonitrile / 2 h / 0 - 20 °C

5.1: 88 percent / BF₃*Et₂O / CHCl₃ / 1 h

6.1: 68 percent / Bu₄NCN / CH₂Cl₂ / 16 h

7.1: 31 percent / Et₃N / Pd(OAc)2 / acetonitrile / 20 h / 80 - 85 °C

With boron trifluoride diethyl etherate; tetra-n-butylammonium cyanide; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium diacetate; In dichloromethane; chloroform; water; acetonitrile; 1.2: Dess-Martin oxidation / 2.1: Wittig reaction / 7.1: Heck reaction;
DOI:10.1021/jo0302197