2-((E)-3-{(4S,5S)-5-[(Z)-(R)-5-(tert-Butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-hex-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propenyl)-6-hydroxy-4-methoxy-benzoic acid methyl ester

Base Information

Chemical Name:2-((E)-3-{(4S,5S)-5-[(Z)-(R)-5-(tert-Butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-hex-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propenyl)-6-hydroxy-4-methoxy-benzoic acid methyl ester
CAS No.:460348-32-7
Molecular Formula:C₃₇H₅₄O₉Si
Molecular Weight:670.916
Hs Code.:

2-((E)-3-{(4S,5S)-5-[(Z)-(R)-5-(tert-Butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-hex-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propenyl)-6-hydroxy-4-methoxy-benzoic acid methyl ester

Synonyms:2-((E)-3-{(4S,5S)-5-[(Z)-(R)-5-(tert-Butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-hex-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propenyl)-6-hydroxy-4-methoxy-benzoic acid methyl ester

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Chemical Property of 2-((E)-3-{(4S,5S)-5-[(Z)-(R)-5-(tert-Butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-hex-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propenyl)-6-hydroxy-4-methoxy-benzoic acid methyl ester

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Technology Process of 2-((E)-3-{(4S,5S)-5-[(Z)-(R)-5-(tert-Butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-hex-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propenyl)-6-hydroxy-4-methoxy-benzoic acid methyl ester

There total 13 articles about 2-((E)-3-{(4S,5S)-5-[(Z)-(R)-5-(tert-Butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-hex-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propenyl)-6-hydroxy-4-methoxy-benzoic acid methyl ester 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: 71.0%

: 460348-08-7
methyl 2-bromo-6-hydroxy-4-methoxybenzoate

: 460348-29-2
tert-Butyl-[(Z)-(R)-5-((4S,5S)-2,2-dimethyl-5-prop-2-ynyl-[1,3]dioxolan-4-yl)-5-(4-methoxy-benzyloxy)-1-methyl-pent-3-enyloxy]-dimethyl-silane

: 460348-32-7
2-((E)-3-{(4S,5S)-5-[(Z)-(R)-5-(tert-Butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-hex-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propenyl)-6-hydroxy-4-methoxy-benzoic acid methyl ester

Guidance literature:: tert-Butyl-[(Z)-(R)-5-((4S,5S)-2,2-dimethyl-5-prop-2-ynyl-[1,3]dioxolan-4-yl)-5-(4-methoxy-benzyloxy)-1-methyl-pent-3-enyloxy]-dimethyl-silane; With bis-(1,2-dimethylpropyl)borane; In tetrahydrofuran; at -25 - 20 ℃; for 2h;

With potassium phosphate; In tetrahydrofuran; water;

methyl 2-bromo-6-hydroxy-4-methoxybenzoate; With [Pd(OAc)2+4TFP]; In 1,2-dimethoxyethane; water; for 8h; Heating;
DOI:10.1016/S0040-4039(02)00870-5

Reference yield:

: 2237-36-7
4-methoxysalicylic acid

: 460348-32-7
2-((E)-3-{(4S,5S)-5-[(Z)-(R)-5-(tert-Butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-hex-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propenyl)-6-hydroxy-4-methoxy-benzoic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: iPr₂NEt / dimethylformamide / 2 h / 20 °C

1.2: oxalyl chloride; DMF / CH₂Cl₂ / -10 - 20 °C

1.3: 48 percent / CH₂Cl₂ / 1 h / 20 °C

2.1: t-BuLi / pentane; diethyl ether / 0.17 h / -78 °C

2.2: 75 percent / Br₂ / pentane; diethyl ether

3.1: CH₂Cl₂ / 20 °C

3.2: 76 percent / Na₂CO₃ / methanol; H₂O / 6 h / 20 °C

4.1: Sia₂BH / tetrahydrofuran / 2 h / -25 - 20 °C

4.2: K₃PO₄ / tetrahydrofuran; H₂O

4.3: 71 percent / [Pd(OAc)2+4TFP] / 1,2-dimethoxy-ethane; H₂O / 8 h / Heating

With tert.-butyl lithium; bis-(1,2-dimethylpropyl)borane; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; pentane; 4.3: Suzuki coupling;
DOI:10.1016/S0040-4039(02)00870-5

Reference yield:

: 193544-52-4
(R)-tert-butyl(dimethyl)(pent-4-yn-2-yloxy)silane

: 460348-32-7
2-((E)-3-{(4S,5S)-5-[(Z)-(R)-5-(tert-Butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-hex-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propenyl)-6-hydroxy-4-methoxy-benzoic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

1.2: 86 percent / I₂ / tetrahydrofuran

2.1: SiaBH / tetrahydrofuran / 3 h / -20 - 0 °C

2.2: 89 percent / AcOH / 3 h / 65 °C

3.1: t-BuLi / diethyl ether; pentane / 0.25 h / -78 °C

3.2: 77 percent / diethyl ether; pentane / -78 - 0 °C

4.1: K₂CO₃ / methanol / 5 h / 20 °C

4.2: 74 percent / CF₃SO₃H / diethyl ether / 4 h / 20 °C

5.1: Sia₂BH / tetrahydrofuran / 2 h / -25 - 20 °C

5.2: K₃PO₄ / tetrahydrofuran; H₂O

5.3: 71 percent / [Pd(OAc)2+4TFP] / 1,2-dimethoxy-ethane; H₂O / 8 h / Heating

With n-butyllithium; tert.-butyl lithium; bis-(1,2-dimethylpropyl)borane; potassium carbonate; In tetrahydrofuran; methanol; diethyl ether; hexane; pentane; 5.3: Suzuki coupling;
DOI:10.1016/S0040-4039(02)00870-5