(2R,3S)-Methyl 2-azido-3-(dimethylphenylsilyl)hex-4-enoate

Base Information

• Chemical Name: (2R,3S)-Methyl 2-azido-3-(dimethylphenylsilyl)hex-4-enoate
• CAS No.: 136824-23-2
• Molecular Formula: C₁₅H₂₁N₃O₂Si
• Molecular Weight: 303.436
• Mol file: 136824-23-2.mol

Synonyms:(2R,3S)-Methyl 2-azido-3-(dimethylphenylsilyl)hex-4-enoate

Chemical Property of (2R,3S)-Methyl 2-azido-3-(dimethylphenylsilyl)hex-4-enoate

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of (2R,3S)-Methyl 2-azido-3-(dimethylphenylsilyl)hex-4-enoate

There total 1 articles about (2R,3S)-Methyl 2-azido-3-(dimethylphenylsilyl)hex-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:

(E)-(3R)-Methyl 3-(dimethylphenylsilyl)hex-4-enoate (136174-52-2) → (2R,3S)-Methyl 2-azido-3-(dimethylphenylsilyl)hex-4-enoate (136824-23-2) + (E)-(2S,3S)-2-Azido-3-(dimethyl-phenyl-silanyl)-hex-4-enoic acid methyl ester (136824-24-3)

Guidance literature:

With n-butyllithium; 2,4,6-Triisopropylbenzenesulfonyl azide; acetic acid; diisopropylamine; Yield given. Multistep reaction; 1. THF, hexanes, -78 deg C, 30 min; 2. THF, -78 deg C to r.t., 8 h;

DOI:10.1021/jo00026a030

Reference yield: 80.0%

2-iodobenzaldehyde (26260-02-6) + (2R,3S)-Methyl 2-azido-3-(dimethylphenylsilyl)hex-4-enoate (136824-23-2) → (4R,5R,6S,E)-methyl 4-azido-6-(2-iodophenyl)-6-methoxy-5-methylhex-2-enoate

Guidance literature:

With Trimethylmethoxysilane; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 - 0 ℃; for 48h; stereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2021.132119

Reference yield: 77.0%

2-bromophenylacetaldehyde (96557-30-1) + (2R,3S)-Methyl 2-azido-3-(dimethylphenylsilyl)hex-4-enoate (136824-23-2) → (4R,5R,6R,E)-methyl 4-azido-7-(2-bromophenyl)-6-methoxy-5-methylhept-2-enoate

Guidance literature:

With Trimethylmethoxysilane; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 - 0 ℃; for 48h; stereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2021.132119

upstream raw materials:

(E)-(3R)-Methyl 3-(dimethylphenylsilyl)hex-4-enoate