[(1S,2S,4R,5S)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-vinyl-cyclohexyl]-(6-bromo-benzo[1,3]dioxol-5-ylmethyl)-amine

Base Information

Chemical Name:[(1S,2S,4R,5S)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-vinyl-cyclohexyl]-(6-bromo-benzo[1,3]dioxol-5-ylmethyl)-amine
CAS No.:186809-22-3
Molecular Formula:C₂₉H₄₀BrNO₄Si
Molecular Weight:574.63
Hs Code.:

Synonyms:[(1S,2S,4R,5S)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-vinyl-cyclohexyl]-(6-bromo-benzo[1,3]dioxol-5-ylmethyl)-amine

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Chemical Property of [(1S,2S,4R,5S)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-vinyl-cyclohexyl]-(6-bromo-benzo[1,3]dioxol-5-ylmethyl)-amine

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Technology Process of [(1S,2S,4R,5S)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-vinyl-cyclohexyl]-(6-bromo-benzo[1,3]dioxol-5-ylmethyl)-amine

There total 21 articles about [(1S,2S,4R,5S)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-vinyl-cyclohexyl]-(6-bromo-benzo[1,3]dioxol-5-ylmethyl)-amine 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: 93.0%

: 186809-21-2
[(1S,2S,4R,5S)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-ethynyl-cyclohexyl]-(6-bromo-benzo[1,3]dioxol-5-ylmethyl)-amine

: 186809-22-3
[(1S,2S,4R,5S)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-vinyl-cyclohexyl]-(6-bromo-benzo[1,3]dioxol-5-ylmethyl)-amine

Guidance literature:: With quinoline; hydrogen; Lindlar's catalyst; In methanol;
DOI:10.1021/ja963900h

Reference yield:

: 186809-16-5
Acetic acid (1S,3R,4S)-3-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-cyano-1-ethynyl-pentyl ester

: 186809-22-3
[(1S,2S,4R,5S)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-vinyl-cyclohexyl]-(6-bromo-benzo[1,3]dioxol-5-ylmethyl)-amine

Guidance literature:: Multi-step reaction with 5 steps

1.1: lithium / tetrahydrofuran / 0 - 20 °C

1.2: CuCN / tetrahydrofuran / 0.5 h / 0 °C

1.3: 84 percent / tetrahydrofuran / -96 - -90 °C

2.1: 78 percent / diisobutylaluminum hydride / toluene; hexane / -78 - 0 °C

3.1: 1,3,5-trimethyl-benzene / Heating

4.1: tetrabutylammonium fluoride / tetrahydrofuran; 1,3,5-trimethyl-benzene / 1 h / 0 °C

5.1: 93 percent / H₂; quinoline / Lindlar catalyst / methanol / 19 h / 20 °C

With quinoline; tetrabutyl ammonium fluoride; hydrogen; lithium; diisobutylaluminium hydride; Lindlar's catalyst; In tetrahydrofuran; methanol; hexane; toluene; 1,3,5-trimethyl-benzene; 1.1: Metallation / 1.2: transmetalation / 1.3: silacupration / 2.1: Reduction / 3.1: imino ene cyclization / 4.1: desylilation / 5.1: Reduction;
DOI:10.1021/ja970839n

Reference yield:

: (3S,4R)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-8-(dimethyl-phenyl-silanyl)-octa-6,7-dienal

: 186809-22-3
[(1S,2S,4R,5S)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-vinyl-cyclohexyl]-(6-bromo-benzo[1,3]dioxol-5-ylmethyl)-amine

Guidance literature:: Multi-step reaction with 3 steps

1: 1,3,5-trimethyl-benzene / Heating

2: tetrabutylammonium fluoride / tetrahydrofuran; 1,3,5-trimethyl-benzene / 1 h / 0 °C

3: 93 percent / H₂; quinoline / Lindlar catalyst / methanol / 19 h / 20 °C

With quinoline; tetrabutyl ammonium fluoride; hydrogen; Lindlar's catalyst; In tetrahydrofuran; methanol; 1,3,5-trimethyl-benzene; 1: imino ene cyclization / 2: desylilation / 3: Reduction;
DOI:10.1021/ja970839n