(2R,3S,Z)-methyl 2-(4-bromophenyl)-3-methyl-5-phenyl-5-(trimethylsilyloxy)pent-4-enoate

Base Information

• Chemical Name: (2R,3S,Z)-methyl 2-(4-bromophenyl)-3-methyl-5-phenyl-5-(trimethylsilyloxy)pent-4-enoate
• CAS No.: 1151770-34-1
• Molecular Formula: C₂₂H₂₇BrO₃Si
• Molecular Weight: 447.444

Synonyms:(2R,3S,Z)-methyl 2-(4-bromophenyl)-3-methyl-5-phenyl-5-(trimethylsilyloxy)pent-4-enoate

Chemical Property of (2R,3S,Z)-methyl 2-(4-bromophenyl)-3-methyl-5-phenyl-5-(trimethylsilyloxy)pent-4-enoate

Chemical Property:

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Technology Process of (2R,3S,Z)-methyl 2-(4-bromophenyl)-3-methyl-5-phenyl-5-(trimethylsilyloxy)pent-4-enoate

There total 3 articles about (2R,3S,Z)-methyl 2-(4-bromophenyl)-3-methyl-5-phenyl-5-(trimethylsilyloxy)pent-4-enoate 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: 75.0%

(Z)-trimethyl((1-phenylbut-1-en-1-yl)oxy)silane (120869-79-6) + methyl 2-(4-bromophenyl)-2-diazoacetate (264881-99-4) → (2R,3S,Z)-methyl 2-(4-bromophenyl)-3-methyl-5-phenyl-5-(trimethylsilyloxy)pent-4-enoate (1151770-34-1) + (2S,3R,Z)-methyl 2-(4-bromophenyl)-3-methyl-5-phenyl-5-(trimethylsilyloxy)pent-4-enoate + (1S,2S,3R)-methyl 1-(4-bromophenyl)-3-ethyl-2-phenyl-2-(trimethylsilyloxy)cyclopropanecarboxylate (1151770-35-2) + (Z)-methyl 2-(4-bromophenyl)-3-methyl-5-phenyl-5-(trimethylsilyloxy)pent-4-enoate

Guidance literature:

With Rh₂[(N-(4-dodecylphenyl)sulfonyl)-(S)-prolinate]4; In 2,2-Dimethylbutane; at 20 ℃; for 19h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2008.11.059

Reference yield: 40.0%

(Z)-trimethyl((1-phenylbut-1-en-1-yl)oxy)silane (120869-79-6) + methyl 2-(4-bromophenyl)-2-diazoacetate (264881-99-4) → (2R,3S,Z)-methyl 2-(4-bromophenyl)-3-methyl-5-phenyl-5-(trimethylsilyloxy)pent-4-enoate (1151770-34-1) + (2S,3R,Z)-methyl 2-(4-bromophenyl)-3-methyl-5-phenyl-5-(trimethylsilyloxy)pent-4-enoate + (1R,2R,3S)-methyl 1-(4-bromophenyl)-3-ethyl-2-phenyl-2-(trimethylsilyloxy)cyclopropanecarboxylate + (1S,2S,3R)-methyl 1-(4-bromophenyl)-3-ethyl-2-phenyl-2-(trimethylsilyloxy)cyclopropanecarboxylate (1151770-35-2) + (Z)-methyl 2-(4-bromophenyl)-3-methyl-5-phenyl-5-(trimethylsilyloxy)pent-4-enoate + methyl 1-(4-bromophenyl)-3-ethyl-2-phenyl-2-(trimethylsilyloxy)cyclopropanecarboxylate

Guidance literature:

With Rh₂(S-biTIPS)2; In 2,2-Dimethylbutane; dichloromethane; at 20 ℃; for 19h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2008.11.059

Reference yield:

(Z)-trimethyl((1-phenylbut-1-en-1-yl)oxy)silane (120869-79-6) + methyl 2-(4-bromophenyl)-2-diazoacetate (264881-99-4) → (2R,3S,Z)-methyl 2-(4-bromophenyl)-3-methyl-5-phenyl-5-(trimethylsilyloxy)pent-4-enoate (1151770-34-1) + (2S,3R,Z)-methyl 2-(4-bromophenyl)-3-methyl-5-phenyl-5-(trimethylsilyloxy)pent-4-enoate + (1R,2R,3S)-methyl 1-(4-bromophenyl)-3-ethyl-2-phenyl-2-(trimethylsilyloxy)cyclopropanecarboxylate + (1S,2S,3R)-methyl 1-(4-bromophenyl)-3-ethyl-2-phenyl-2-(trimethylsilyloxy)cyclopropanecarboxylate (1151770-35-2) + (Z)-methyl 2-(4-bromophenyl)-3-methyl-5-phenyl-5-(trimethylsilyloxy)pent-4-enoate

Guidance literature:

With Rh₂(S-PTAD)4; In 2,2-Dimethylbutane; at 20 ℃; for 19h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2008.11.059

upstream raw materials:

(Z)-trimethyl((1-phenylbut-1-en-1-yl)oxy)silane

methyl 2-(4-bromophenyl)-2-diazoacetate

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