4-bromo-3-[(2S,3R)-2-hydroxy-3-methoxymethyl-6,7-dimethyl-3-(2-trimethylsilylethoxycarbonyl)oct-6-enyl]benzoic acid methyl ester

Base Information

Chemical Name:4-bromo-3-[(2S,3R)-2-hydroxy-3-methoxymethyl-6,7-dimethyl-3-(2-trimethylsilylethoxycarbonyl)oct-6-enyl]benzoic acid methyl ester
CAS No.:840524-78-9
Molecular Formula:C₂₆H₄₁BrO₆Si
Molecular Weight:557.597
Hs Code.:

Synonyms:4-bromo-3-[(2S,3R)-2-hydroxy-3-methoxymethyl-6,7-dimethyl-3-(2-trimethylsilylethoxycarbonyl)oct-6-enyl]benzoic acid methyl ester

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Chemical Property of 4-bromo-3-[(2S,3R)-2-hydroxy-3-methoxymethyl-6,7-dimethyl-3-(2-trimethylsilylethoxycarbonyl)oct-6-enyl]benzoic acid methyl ester

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Technology Process of 4-bromo-3-[(2S,3R)-2-hydroxy-3-methoxymethyl-6,7-dimethyl-3-(2-trimethylsilylethoxycarbonyl)oct-6-enyl]benzoic acid methyl ester

There total 10 articles about 4-bromo-3-[(2S,3R)-2-hydroxy-3-methoxymethyl-6,7-dimethyl-3-(2-trimethylsilylethoxycarbonyl)oct-6-enyl]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: 47.0%

: 840524-76-7
(R)-4-bromo-3-[3-methoxymethyl-6,7-dimethyl-2-oxo-3-(2-trimethylsilylethoxycarbonyl)oct-6-enyl]benzoic acid methyl ester

: 840524-77-8
4-bromo-3-[(2R,3R)-2-hydroxy-3-methoxymethyl-6,7-dimethyl-3-(2-trimethylsilylethoxycarbonyl)oct-6-enyl]benzoic acid methyl ester

: 840524-78-9
4-bromo-3-[(2S,3R)-2-hydroxy-3-methoxymethyl-6,7-dimethyl-3-(2-trimethylsilylethoxycarbonyl)oct-6-enyl]benzoic acid methyl ester

Guidance literature:: With sodium tetrahydroborate; In methanol; at 0 ℃; for 2.5h;
DOI:10.1002/anie.200461327

Reference yield:

: 2916-68-9
2-(Trimethylsilyl)ethanol

: 840524-78-9
4-bromo-3-[(2S,3R)-2-hydroxy-3-methoxymethyl-6,7-dimethyl-3-(2-trimethylsilylethoxycarbonyl)oct-6-enyl]benzoic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 77 percent / 1,3-dicyclohexylcarbodiimide; DMAP / CH₂Cl₂ / 72 h / 20 °C

2: aq. KOH / methanol / 15 h / 45 °C

3: 1.08 g / cyanuric fluoride; pyridine / CH₂Cl₂ / 1 h / 0 °C

4: 63 percent / hexamethyldisilazane; n-BuLi / diethyl ether / 0 - 20 °C

5: 78 percent / aq. NaCl / dimethylsulfoxide / 20 h / 125 °C

6: 36 percent / NaBH₄ / methanol / 2.5 h / 0 °C

With pyridine; dmap; potassium hydroxide; sodium tetrahydroborate; n-butyllithium; trifluoro-[1,3,5]triazine; dicyclohexyl-carbodiimide; 1,1,1,3,3,3-hexamethyl-disilazane; sodium chloride; In methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; 5: Krapcho decarboxylation;
DOI:10.1002/anie.200461327

Reference yield:

: 216320-01-3
5-iodo-2,3-dimethyl-2-pentene

: 840524-78-9
4-bromo-3-[(2S,3R)-2-hydroxy-3-methoxymethyl-6,7-dimethyl-3-(2-trimethylsilylethoxycarbonyl)oct-6-enyl]benzoic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: NaH / dimethylformamide / 72 h

2: 3.92 g / NaH / tetrahydrofuran / 1 h

3: porcine liver esterase; aq. phosphate buffer / dimethylsulfoxide / 168 h / 20 °C / pH 8.0

4: 77 percent / 1,3-dicyclohexylcarbodiimide; DMAP / CH₂Cl₂ / 72 h / 20 °C

5: aq. KOH / methanol / 15 h / 45 °C

6: 1.08 g / cyanuric fluoride; pyridine / CH₂Cl₂ / 1 h / 0 °C

7: 63 percent / hexamethyldisilazane; n-BuLi / diethyl ether / 0 - 20 °C

8: 78 percent / aq. NaCl / dimethylsulfoxide / 20 h / 125 °C

9: 36 percent / NaBH₄ / methanol / 2.5 h / 0 °C

With pyridine; porcine liver esterase; dmap; potassium hydroxide; sodium tetrahydroborate; n-butyllithium; trifluoro-[1,3,5]triazine; phosphate buffer; sodium hydride; dicyclohexyl-carbodiimide; 1,1,1,3,3,3-hexamethyl-disilazane; sodium chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 8: Krapcho decarboxylation;
DOI:10.1002/anie.200461327