1R-<1α(αS^*,βS^*),2β,5α>-(+/-)-tert-butyl 5-bromo-α-ethenyl-β,2-dihydroxy-2,6,6-trimethylcyclohexanebutanoate

Base Information

• Chemical Name: 1R-<1α(αS^*,βS^*),2β,5α>-(+/-)-tert-butyl 5-bromo-α-ethenyl-β,2-dihydroxy-2,6,6-trimethylcyclohexanebutanoate
• CAS No.: 83220-43-3
• Molecular Formula: C₁₉H₃₃BrO₄
• Molecular Weight: 405.373

Synonyms:1R-<1α(αS^*,βS^*),2β,5α>-(+/-)-tert-butyl 5-bromo-α-ethenyl-β,2-dihydroxy-2,6,6-trimethylcyclohexanebutanoate

Chemical Property of 1R-<1α(αS^*,βS^*),2β,5α>-(+/-)-tert-butyl 5-bromo-α-ethenyl-β,2-dihydroxy-2,6,6-trimethylcyclohexanebutanoate

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 1R-<1α(αS^*,βS^*),2β,5α>-(+/-)-tert-butyl 5-bromo-α-ethenyl-β,2-dihydroxy-2,6,6-trimethylcyclohexanebutanoate

There total 4 articles about 1R-<1α(αS^*,βS^*),2β,5α>-(+/-)-tert-butyl 5-bromo-α-ethenyl-β,2-dihydroxy-2,6,6-trimethylcyclohexanebutanoate 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: 41.0%

((1S,3S,6S)-3-Bromo-6-hydroxy-2,2,6-trimethyl-cyclohexyl)-acetaldehyde + Lithium; (Z)-1-tert-butoxy-buta-1,3-dien-1-olate → Lithium; (3aR,5R,7aR)-5-bromo-4,4,7a-trimethyl-octahydro-benzofuran-2-olate + 1R-<1α(αS*,βS*),2β,5α>-(+/-)-tert-butyl 5-bromo-α-ethenyl-β,2-dihydroxy-2,6,6-trimethylcyclohexanebutanoate (83220-43-3) + 1R-<1α(αR*,βS*),2β,5α>-(+/-)-tert-butyl 5-bromo-α-ethenyl-β,2-dihydroxy-2,6,6-trimethylcyclohexanebutanoate (83289-28-5)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -23 ℃; for 2h;

DOI:10.1021/ja00388a038

Reference yield:

t-butyl vinylacetate (14036-55-6) → 1R-<1α(αS*,βS*),2β,5α>-(+/-)-tert-butyl 5-bromo-α-ethenyl-β,2-dihydroxy-2,6,6-trimethylcyclohexanebutanoate (83220-43-3)

Guidance literature:

Multi-step reaction with 2 steps

1: LDA

2: LDA / hexamethylphosphoric acid triamide

With lithium diisopropyl amide; In N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1021/ja00388a038

Reference yield:

tert-butyl (E)-crotonate (79218-15-8) → 1R-<1α(αS*,βS*),2β,5α>-(+/-)-tert-butyl 5-bromo-α-ethenyl-β,2-dihydroxy-2,6,6-trimethylcyclohexanebutanoate (83220-43-3)

Guidance literature:

Multi-step reaction with 2 steps

1: LDA

2: LDA / hexamethylphosphoric acid triamide

With lithium diisopropyl amide; In N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1021/ja00388a038

upstream raw materials:

t-butyl vinylacetate

tert-butyl (E)-crotonate

Downstream raw materials:

1R-<1α(αS^*,βS^*),2β,5α>-(+/-)-tert-butyl 5-bromo-α-ethenyl-2-hydroxy-2,6,6-trimethyl-β-(4-nitrobenzoyloxy)cyclohexanebutanoate

4-Nitro-benzoic acid (3aS,4aS,7S,8aS,10R,10aS)-7-bromo-4a,8,8-trimethyl-1-oxo-dodecahydro-2,4-dioxa-benzo[f]azulen-10-yl ester

(3aα,4aβ,7β,8aα,10α,10aα)-(+/-)-7-bromodecahydro-4a,8,8-trimethyl-10-(4-nitrobenzoyloxy)furo<3,4-b>-1-benzoxepin-1(3H)-one

(2α,3α,4β,5aβ,7α,9aα)-(+/-)-7-bromo-2-(bromomethyl)decahydro-6,6,9a-trimethyl-4-(4-nitrobenzoyloxy)-1-benzoxepin-3-carboxylic acid

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