methyl (S)-(Z)-6-aza-8-hydroxy-7-methyl-6-(p-toluenesulfonyl)oct-2-enoate

Base Information

• Chemical Name: methyl (S)-(Z)-6-aza-8-hydroxy-7-methyl-6-(p-toluenesulfonyl)oct-2-enoate
• CAS No.: 903516-11-0
• Molecular Formula: C₁₆H₂₃NO₅S
• Molecular Weight: 341.428

Synonyms:methyl (S)-(Z)-6-aza-8-hydroxy-7-methyl-6-(p-toluenesulfonyl)oct-2-enoate

Chemical Property of methyl (S)-(Z)-6-aza-8-hydroxy-7-methyl-6-(p-toluenesulfonyl)oct-2-enoate

Chemical Property:

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Technology Process of methyl (S)-(Z)-6-aza-8-hydroxy-7-methyl-6-(p-toluenesulfonyl)oct-2-enoate

There total 2 articles about methyl (S)-(Z)-6-aza-8-hydroxy-7-methyl-6-(p-toluenesulfonyl)oct-2-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:

(5S)-4-aza-1-hydroxy-5-methyl-7-oxa-4-(p-toluenesulfonyl)cycloheptane (767288-12-0) + bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate (88738-78-7) → methyl (S)-(Z)-6-aza-8-hydroxy-7-methyl-6-(p-toluenesulfonyl)oct-2-enoate (903516-11-0) + methyl (2E,7S)-6-aza-8-hydroxy-7-methyl-6-(p-toluenesulfonyl)oct-2-enoate

Guidance literature:

bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate; With 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 1h;

(5S)-4-aza-1-hydroxy-5-methyl-7-oxa-4-(p-toluenesulfonyl)cycloheptane; In tetrahydrofuran; toluene; at -78 ℃; for 72h;

DOI:10.1021/jo060495w

Reference yield:

(5S)-4-aza-1-hydroxy-5-methyl-7-oxa-4-(p-toluenesulfonyl)cycloheptane (767288-12-0) + methyl (triphenylphosphoranylidene)acetate (21204-67-1,2605-67-6) → methyl (S)-(Z)-6-aza-8-hydroxy-7-methyl-6-(p-toluenesulfonyl)oct-2-enoate (903516-11-0) + methyl (2E,7S)-6-aza-8-hydroxy-7-methyl-6-(p-toluenesulfonyl)oct-2-enoate

Guidance literature:

With benzoic acid; In toluene; at 90 ℃; for 1h; Title compound not separated from byproducts;

DOI:10.1021/jo060495w

Reference yield: 83.0%

methyl (S)-(Z)-6-aza-8-hydroxy-7-methyl-6-(p-toluenesulfonyl)oct-2-enoate (903516-11-0) → methyl (7S)-(2Z)-6-aza-8-bromo-7-methyl-6-(p-toluenesulfonyl)oct-2-enoate (903516-12-1)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1021/jo060495w

upstream raw materials:

(5S)-4-aza-1-hydroxy-5-methyl-7-oxa-4-(p-toluenesulfonyl)cycloheptane

bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate

methyl (triphenylphosphoranylidene)acetate

Downstream raw materials:

methyl (7S)-(2Z)-6-aza-8-bromo-7-methyl-6-(p-toluenesulfonyl)oct-2-enoate

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