2-Bromo-6-hydroxy-4-methoxy-benzoic acid (Z)-(S)-5-((4S,5S)-2,2-dimethyl-5-prop-2-ynyl-[1,3]dioxolan-4-yl)-5-(4-methoxy-benzyloxy)-1-methyl-pent-3-enyl ester

Base Information

Chemical Name:2-Bromo-6-hydroxy-4-methoxy-benzoic acid (Z)-(S)-5-((4S,5S)-2,2-dimethyl-5-prop-2-ynyl-[1,3]dioxolan-4-yl)-5-(4-methoxy-benzyloxy)-1-methyl-pent-3-enyl ester
CAS No.:460348-31-6
Molecular Formula:C₃₀H₃₅BrO₈
Molecular Weight:603.507
Hs Code.:

Synonyms:2-Bromo-6-hydroxy-4-methoxy-benzoic acid (Z)-(S)-5-((4S,5S)-2,2-dimethyl-5-prop-2-ynyl-[1,3]dioxolan-4-yl)-5-(4-methoxy-benzyloxy)-1-methyl-pent-3-enyl ester

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Chemical Property of 2-Bromo-6-hydroxy-4-methoxy-benzoic acid (Z)-(S)-5-((4S,5S)-2,2-dimethyl-5-prop-2-ynyl-[1,3]dioxolan-4-yl)-5-(4-methoxy-benzyloxy)-1-methyl-pent-3-enyl ester

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Technology Process of 2-Bromo-6-hydroxy-4-methoxy-benzoic acid (Z)-(S)-5-((4S,5S)-2,2-dimethyl-5-prop-2-ynyl-[1,3]dioxolan-4-yl)-5-(4-methoxy-benzyloxy)-1-methyl-pent-3-enyl ester

There total 13 articles about 2-Bromo-6-hydroxy-4-methoxy-benzoic acid (Z)-(S)-5-((4S,5S)-2,2-dimethyl-5-prop-2-ynyl-[1,3]dioxolan-4-yl)-5-(4-methoxy-benzyloxy)-1-methyl-pent-3-enyl 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: 76.0%

: 460348-10-1
2-bromo-6-hydroxy-4-methoxy-benzoic acid

: 460348-30-5
(Z)-(S)-6-((4S,5S)-2,2-Dimethyl-5-prop-2-ynyl-[1,3]dioxolan-4-yl)-6-(4-methoxy-benzyloxy)-hex-4-en-2-ol

: 460348-31-6
2-Bromo-6-hydroxy-4-methoxy-benzoic acid (Z)-(S)-5-((4S,5S)-2,2-dimethyl-5-prop-2-ynyl-[1,3]dioxolan-4-yl)-5-(4-methoxy-benzyloxy)-1-methyl-pent-3-enyl ester

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 5h;
DOI:10.1016/S0040-4039(02)00870-5

Reference yield:

: 2237-36-7
4-methoxysalicylic acid

: 460348-31-6
2-Bromo-6-hydroxy-4-methoxy-benzoic acid (Z)-(S)-5-((4S,5S)-2,2-dimethyl-5-prop-2-ynyl-[1,3]dioxolan-4-yl)-5-(4-methoxy-benzyloxy)-1-methyl-pent-3-enyl ester

Guidance literature:: Multi-step reaction with 5 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: 100 percent / NaOH / 1,2-dimethoxy-ethane; H₂O / Heating

5.1: 76 percent / DCC; DMAP / CH₂Cl₂ / 5 h / 20 °C

With dmap; sodium hydroxide; tert.-butyl lithium; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In 1,2-dimethoxyethane; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; pentane;
DOI:10.1016/S0040-4039(02)00870-5

Reference yield:

: 150406-35-2
(S)-tert-butyldimethyl(pent-4-yn-2-yloxy)silane

: 460348-31-6
2-Bromo-6-hydroxy-4-methoxy-benzoic acid (Z)-(S)-5-((4S,5S)-2,2-dimethyl-5-prop-2-ynyl-[1,3]dioxolan-4-yl)-5-(4-methoxy-benzyloxy)-1-methyl-pent-3-enyl ester

Guidance literature:: Multi-step reaction with 6 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: 56 percent / diethyl ether; pentane / -78 - 0 °C

4.1: K₂CO₃ / methanol / 5 h / 20 °C

4.2: 72 percent / CF₃SO₃H / diethyl ether / 4 h / 20 °C

5.1: 97 percent / TBAF / tetrahydrofuran / 10 h / 20 °C

6.1: 76 percent / DCC; DMAP / CH₂Cl₂ / 5 h / 20 °C

With dmap; n-butyllithium; tetrabutyl ammonium fluoride; tert.-butyl lithium; bis-(1,2-dimethylpropyl)borane; potassium carbonate; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; pentane;
DOI:10.1016/S0040-4039(02)00870-5