{(Z)-(1R,2S)-5-Bromo-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2,4-dimethyl-pent-3-enyloxy}-tert-butyl-dimethyl-silane

Base Information

Chemical Name:{(Z)-(1R,2S)-5-Bromo-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2,4-dimethyl-pent-3-enyloxy}-tert-butyl-dimethyl-silane
CAS No.:827603-05-4
Molecular Formula:C₂₄H₄₁BrO₃Si
Molecular Weight:485.577
Hs Code.:

Synonyms:{(Z)-(1R,2S)-5-Bromo-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2,4-dimethyl-pent-3-enyloxy}-tert-butyl-dimethyl-silane

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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 {(Z)-(1R,2S)-5-Bromo-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2,4-dimethyl-pent-3-enyloxy}-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of {(Z)-(1R,2S)-5-Bromo-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2,4-dimethyl-pent-3-enyloxy}-tert-butyl-dimethyl-silane

There total 10 articles about {(Z)-(1R,2S)-5-Bromo-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2,4-dimethyl-pent-3-enyloxy}-tert-butyl-dimethyl-silane 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:

: 496035-35-9
(2S,4S)-1-hydroxy-5-(p-methoxybenzyloxy)-2,4-dimethylpentan-3-one

: 827603-05-4
{(Z)-(1R,2S)-5-Bromo-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2,4-dimethyl-pent-3-enyloxy}-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 6 steps

1.1: dicyclohexylboron chloride; triethylamine / diethyl ether

1.2: LiBH₄ / diethyl ether

2.1: TEMPO; bis-acetoxyiodobenzene / CH₂Cl₂ / 3 h / 20 °C

3.1: KHMDS; 18-crown-6 / tetrahydrofuran; toluene / 0.5 h / -78 °C

3.2: tetrahydrofuran; toluene / 0.67 h

4.1: 1.64 g / 2,6-lutidine / CH₂Cl₂ / 4 h / -78 °C

5.1: 90 percent / DIBAL-H / CH₂Cl₂; hexane / 1 h / -78 °C

6.1: CBr₄; PPh₃

With 2,6-dimethylpyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; 18-crown-6 ether; carbon tetrabromide; [bis(acetoxy)iodo]benzene; dicyclohexylboron chloride; potassium hexamethylsilazane; diisobutylaluminium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene;
DOI:10.1021/jo048534w

Reference yield:

: (2R,3R,4S,5S)-6-(4-Methoxy-benzyloxy)-3,5-dimethyl-hexane-1,2,4-triol

: 827603-05-4
{(Z)-(1R,2S)-5-Bromo-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2,4-dimethyl-pent-3-enyloxy}-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 5 steps

1.1: 296 mg / sodium periodate; sodium bicarbonate / methanol; H₂O / 0.17 h / 20 °C / pH 7

2.1: KHMDS; 18-crown-6 / tetrahydrofuran; toluene / 0.5 h / -78 °C

2.2: tetrahydrofuran; toluene / 0.67 h

3.1: 1.64 g / 2,6-lutidine / CH₂Cl₂ / 4 h / -78 °C

4.1: 90 percent / DIBAL-H / CH₂Cl₂; hexane / 1 h / -78 °C

5.1: CBr₄; PPh₃

With 2,6-dimethylpyridine; sodium periodate; 18-crown-6 ether; carbon tetrabromide; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; triphenylphosphine; In tetrahydrofuran; methanol; hexane; dichloromethane; water; toluene;
DOI:10.1021/jo048534w

Reference yield:

: 827603-03-2
(2S,4S,5R)-6-(tert-butyldimethylsilyloxy)-5-hydroxy-1-(4-methoxybenzyloxy)-2,4-dimethylhexan-3-one

: 827603-05-4
{(Z)-(1R,2S)-5-Bromo-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2,4-dimethyl-pent-3-enyloxy}-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 7 steps

1.1: 99 percent / Me₄NHB(OAc)3; acetic acid; camphorsulfonic acid / acetonitrile / 18 h / -40 - -22 °C

2.1: hydrochloric acid / methanol; H₂O / 0.08 h / 20 °C

3.1: 296 mg / sodium periodate; sodium bicarbonate / methanol; H₂O / 0.17 h / 20 °C / pH 7

4.1: KHMDS; 18-crown-6 / tetrahydrofuran; toluene / 0.5 h / -78 °C

4.2: tetrahydrofuran; toluene / 0.67 h

5.1: 1.64 g / 2,6-lutidine / CH₂Cl₂ / 4 h / -78 °C

6.1: 90 percent / DIBAL-H / CH₂Cl₂; hexane / 1 h / -78 °C

7.1: CBr₄; PPh₃

With 2,6-dimethylpyridine; hydrogenchloride; sodium periodate; 18-crown-6 ether; carbon tetrabromide; camphor-10-sulfonic acid; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; acetic acid; triphenylphosphine; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; hexane; dichloromethane; water; toluene; acetonitrile;
DOI:10.1021/jo048534w