methyl (5S,6R)-6-((S)-2-azido-2-phenylethoxy)-6-(2-bromophenyl)-5-methylhex-3-ynoate

Base Information

• Chemical Name: methyl (5S,6R)-6-((S)-2-azido-2-phenylethoxy)-6-(2-bromophenyl)-5-methylhex-3-ynoate
• CAS No.: 1204508-82-6
• Molecular Formula: C₂₂H₂₂BrN₃O₃
• Molecular Weight: 456.339

Synonyms:methyl (5S,6R)-6-((S)-2-azido-2-phenylethoxy)-6-(2-bromophenyl)-5-methylhex-3-ynoate

Chemical Property of methyl (5S,6R)-6-((S)-2-azido-2-phenylethoxy)-6-(2-bromophenyl)-5-methylhex-3-ynoate

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Technology Process of methyl (5S,6R)-6-((S)-2-azido-2-phenylethoxy)-6-(2-bromophenyl)-5-methylhex-3-ynoate

There total 1 articles about methyl (5S,6R)-6-((S)-2-azido-2-phenylethoxy)-6-(2-bromophenyl)-5-methylhex-3-ynoate 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: 92.0%

(Ra)-methyl 3-(dimethyl(phenyl)silyl)hexa-3,4-dienoate + (S)-(2-azido-2-phenylethoxy)(tert-butyl)dimethylsilane (1204508-42-8) + ortho-bromobenzaldehyde (6630-33-7) → methyl (5S,6R)-6-((S)-2-azido-2-phenylethoxy)-6-(2-bromophenyl)-5-methylhex-3-ynoate (1204508-82-6)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In propiononitrile; at -78 ℃; for 12h; optical yield given as %de; Inert atmosphere;

DOI:10.1021/ol902681t

Reference yield: 67.0%

methyl (5S,6R)-6-((S)-2-azido-2-phenylethoxy)-6-(2-bromophenyl)-5-methylhex-3-ynoate (1204508-82-6) → methyl 2-((4S,5R,8S)-5-(2-bromophenyl)-4-methyl-8-phenyl-4,5,7,8-tetrahydro-[1,2,3]triazolo[1,5-d][1,4]oxazepin-3-yl)acetate (1204509-46-5)

Guidance literature:

In toluene; at 130 ℃; for 40h; regioselective reaction; Inert atmosphere;

DOI:10.1021/ol902681t

upstream raw materials:

(S)-(2-azido-2-phenylethoxy)(tert-butyl)dimethylsilane

ortho-bromobenzaldehyde

Downstream raw materials:

methyl 2-((4S,5R,8S)-5-(2-bromophenyl)-4-methyl-8-phenyl-4,5,7,8-tetrahydro-[1,2,3]triazolo[1,5-d][1,4]oxazepin-3-yl)acetate

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