ethyl (1S,2S,5S,6S)-6-((4-bromobenzyl)carbamoyl)-5-(hydroxymethyl)-4-methyl-2-propyl-3-((triisopropylsilyl)oxy)cyclohex-3-ene-1-carboxylate

Base Information

Chemical Name:ethyl (1S,2S,5S,6S)-6-((4-bromobenzyl)carbamoyl)-5-(hydroxymethyl)-4-methyl-2-propyl-3-((triisopropylsilyl)oxy)cyclohex-3-ene-1-carboxylate
CAS No.:1579293-66-5
Molecular Formula:C₃₁H₅₀BrNO₅Si
Molecular Weight:624.731
Hs Code.:

ethyl (1S,2S,5S,6S)-6-((4-bromobenzyl)carbamoyl)-5-(hydroxymethyl)-4-methyl-2-propyl-3-((triisopropylsilyl)oxy)cyclohex-3-ene-1-carboxylate

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Chemical Property of ethyl (1S,2S,5S,6S)-6-((4-bromobenzyl)carbamoyl)-5-(hydroxymethyl)-4-methyl-2-propyl-3-((triisopropylsilyl)oxy)cyclohex-3-ene-1-carboxylate

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Technology Process of ethyl (1S,2S,5S,6S)-6-((4-bromobenzyl)carbamoyl)-5-(hydroxymethyl)-4-methyl-2-propyl-3-((triisopropylsilyl)oxy)cyclohex-3-ene-1-carboxylate

There total 5 articles about ethyl (1S,2S,5S,6S)-6-((4-bromobenzyl)carbamoyl)-5-(hydroxymethyl)-4-methyl-2-propyl-3-((triisopropylsilyl)oxy)cyclohex-3-ene-1-carboxylate 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: 51.0%

: 1579293-65-4
ethyl (3aS,4S,5S,7aS)-7-methyl-3-oxo-5-propyl-6-((triisopropylsilyl)oxy)-1,3,3a,4,5,7a-hexahydroisobenzofuran-4-carboxylate

: 3959-07-7
4-Bromobenzylamine

: 1579293-66-5
ethyl (1S,2S,5S,6S)-6-((4-bromobenzyl)carbamoyl)-5-(hydroxymethyl)-4-methyl-2-propyl-3-((triisopropylsilyl)oxy)cyclohex-3-ene-1-carboxylate

Guidance literature:: In tetrahydrofuran; at 23 ℃; for 30h; Inert atmosphere;
DOI:10.1021/ja501005g

Reference yield:

: 96-04-8
2,3-heptanedione

: 1579293-66-5
ethyl (1S,2S,5S,6S)-6-((4-bromobenzyl)carbamoyl)-5-(hydroxymethyl)-4-methyl-2-propyl-3-((triisopropylsilyl)oxy)cyclohex-3-ene-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: dichloromethane / 30 h / 23 °C / Inert atmosphere

2.1: triethylamine / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

2.2: 24.5 h / 0 - 23 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / dichloromethane / 2 h / -78 °C / Inert atmosphere

3.2: -78 °C / Inert atmosphere

4.1: (S)-(-)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole; 2,6-dimethylpyridine; potassium phosphate / dichloromethane / 18 h / 23 °C / Inert atmosphere

5.1: tetrahydrofuran / 30 h / 23 °C / Inert atmosphere

With 2,6-dimethylpyridine; potassium phosphate; (S)-(-)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja501005g

Reference yield:

: 1579293-42-7
ethyl (Z)-3-methyl-4-oxooct-2-enoate

: 1579293-66-5
ethyl (1S,2S,5S,6S)-6-((4-bromobenzyl)carbamoyl)-5-(hydroxymethyl)-4-methyl-2-propyl-3-((triisopropylsilyl)oxy)cyclohex-3-ene-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: triethylamine / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

1.2: 24.5 h / 0 - 23 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / dichloromethane / 2 h / -78 °C / Inert atmosphere

2.2: -78 °C / Inert atmosphere

3.1: (S)-(-)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole; 2,6-dimethylpyridine; potassium phosphate / dichloromethane / 18 h / 23 °C / Inert atmosphere

4.1: tetrahydrofuran / 30 h / 23 °C / Inert atmosphere

With 2,6-dimethylpyridine; potassium phosphate; (S)-(-)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja501005g