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

Base Information

Chemical Name:(1R,2S)-2-methyl-1-(3',4',5',6-tetramethoxy-4,5-methylenedioxybiphenyl-2-yl)-3-[(triisopropylsilyloxy)methyl]but-3-en-1-ol
CAS No.:1441119-49-8
Molecular Formula:C₃₂H₄₈O₈Si
Molecular Weight:588.814
Hs Code.:

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

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

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

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

: 1441119-47-6
(E)-1-[(3',4',5',6-tetramethoxy-4,5-methylenedioxybiphenyl-2-yl)methoxy]-2-(triisopropylsilyloxymethyl)but-2-ene

: 1441119-49-8
(1R,2S)-2-methyl-1-(3',4',5',6-tetramethoxy-4,5-methylenedioxybiphenyl-2-yl)-3-[(triisopropylsilyloxy)methyl]but-3-en-1-ol

: (1S,2R)-2-methyl-1-(3',4',5',6-tetramethoxy-4,5-methylenedioxybiphenyl-2-yl)-3-[(triisopropylsilyloxy)methyl]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 8h; Overall yield = 54 %; enantioselective reaction; Inert atmosphere;
DOI:10.1002/ejoc.201201247

Reference yield:

: 418755-58-5
6-bromo-7-methoxybenzo[1,3]dioxole-5-carboxylic acid ethyl ester

: 1441119-49-8
(1R,2S)-2-methyl-1-(3',4',5',6-tetramethoxy-4,5-methylenedioxybiphenyl-2-yl)-3-[(triisopropylsilyloxy)methyl]but-3-en-1-ol

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

Guidance literature:: Multi-step reaction with 4 steps

1: diisobutylaluminium hydride / toluene / -78 °C

2: CyJohnPhos; potassium phosphate; palladium diacetate / toluene / 80 °C / Inert atmosphere

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

4: n-butyllithium; 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline] / diethyl ether; hexane / 8 h / -78 °C / Inert atmosphere

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

Reference yield:

: 1192659-02-1
(6-bromo-7-methoxybenzo[d][1,3] dioxol-5-yl-)methanol

: 1441119-49-8
(1R,2S)-2-methyl-1-(3',4',5',6-tetramethoxy-4,5-methylenedioxybiphenyl-2-yl)-3-[(triisopropylsilyloxy)methyl]but-3-en-1-ol

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

Guidance literature:: Multi-step reaction with 3 steps

1: CyJohnPhos; potassium phosphate; palladium diacetate / toluene / 80 °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 / 8 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