(1R,2S)-2-methyl-3-[(triisopropylsilyloxy)methyl]-1-(4,5,6-trimethoxy-3',4'-methylenedioxybiphenyl-2-yl)but-3-en-1-ol

Base Information

Chemical Name:(1R,2S)-2-methyl-3-[(triisopropylsilyloxy)methyl]-1-(4,5,6-trimethoxy-3',4'-methylenedioxybiphenyl-2-yl)but-3-en-1-ol
CAS No.:1441119-48-7
Molecular Formula:C₃₁H₄₆O₇Si
Molecular Weight:558.788
Hs Code.:

Synonyms:(1R,2S)-2-methyl-3-[(triisopropylsilyloxy)methyl]-1-(4,5,6-trimethoxy-3',4'-methylenedioxybiphenyl-2-yl)but-3-en-1-ol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1R,2S)-2-methyl-3-[(triisopropylsilyloxy)methyl]-1-(4,5,6-trimethoxy-3',4'-methylenedioxybiphenyl-2-yl)but-3-en-1-ol

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Technology Process of (1R,2S)-2-methyl-3-[(triisopropylsilyloxy)methyl]-1-(4,5,6-trimethoxy-3',4'-methylenedioxybiphenyl-2-yl)but-3-en-1-ol

There total 4 articles about (1R,2S)-2-methyl-3-[(triisopropylsilyloxy)methyl]-1-(4,5,6-trimethoxy-3',4'-methylenedioxybiphenyl-2-yl)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: 74.0%

: (E)-2-(triisopropylsilyloxymethyl)-1-[(4,5,6-trimethoxy-3',4'-methylenedioxybiphenyl-2-yl)methoxy]but-2-ene

: 1441119-48-7
(1R,2S)-2-methyl-3-[(triisopropylsilyloxy)methyl]-1-(4,5,6-trimethoxy-3',4'-methylenedioxybiphenyl-2-yl)but-3-en-1-ol

Guidance literature:: With n-butyllithium; 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline]; In diethyl ether; hexane; at -78 ℃; for 4h; enantioselective reaction; Inert atmosphere;
DOI:10.1002/ejoc.201201247

Reference yield:

: 73252-54-7
(2-bromo-3,4,5-trimethoxyphenyl)methanol

: 1441119-48-7
(1R,2S)-2-methyl-3-[(triisopropylsilyloxy)methyl]-1-(4,5,6-trimethoxy-3',4'-methylenedioxybiphenyl-2-yl)but-3-en-1-ol

Guidance literature:: Multi-step reaction with 3 steps

1: CyJohnPhos; potassium phosphate; palladium diacetate / toluene / 10 h / 80 - 90 °C / Inert atmosphere

2: potassium tert-butylate / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

3: n-butyllithium; 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline] / diethyl ether; hexane / 4 h / -78 °C / Inert atmosphere

With potassium phosphate; n-butyllithium; potassium tert-butylate; palladium diacetate; 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline]; CyJohnPhos; In tetrahydrofuran; diethyl ether; hexane; toluene; 1: |Suzuki Coupling / 2: |Williamson Ether Synthesis / 3: |[2,3]-Wittig Rearrangement;
DOI:10.1002/ejoc.201201247

Reference yield:

: 1441119-44-3
(2-(benzo[d][1,3]dioxol-5-yl)-3,4,5-trimethoxyphenyl)methanol

: 1441119-48-7
(1R,2S)-2-methyl-3-[(triisopropylsilyloxy)methyl]-1-(4,5,6-trimethoxy-3',4'-methylenedioxybiphenyl-2-yl)but-3-en-1-ol

Guidance literature:: Multi-step reaction with 2 steps

1: potassium tert-butylate / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

2: n-butyllithium; 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline] / diethyl ether; hexane / 4 h / -78 °C / Inert atmosphere

With n-butyllithium; potassium tert-butylate; 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline]; In tetrahydrofuran; diethyl ether; hexane; 1: |Williamson Ether Synthesis / 2: |[2,3]-Wittig Rearrangement;
DOI:10.1002/ejoc.201201247