2-benzyl-5-tert-butoxycarbonylamino-4-fluoro-6-methyl-hept-3-enoic acid

Base Information

• Chemical Name: 2-benzyl-5-tert-butoxycarbonylamino-4-fluoro-6-methyl-hept-3-enoic acid
• CAS No.: 919121-10-1
• Molecular Formula: C₂₀H₂₈FNO₄
• Molecular Weight: 365.445

Synonyms:2-benzyl-5-tert-butoxycarbonylamino-4-fluoro-6-methyl-hept-3-enoic acid

Chemical Property of 2-benzyl-5-tert-butoxycarbonylamino-4-fluoro-6-methyl-hept-3-enoic acid

Chemical Property:

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Technology Process of 2-benzyl-5-tert-butoxycarbonylamino-4-fluoro-6-methyl-hept-3-enoic acid

There total 4 articles about 2-benzyl-5-tert-butoxycarbonylamino-4-fluoro-6-methyl-hept-3-enoic acid 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%

(2R,5S,3Z)-2-benzyl-5-[N-(tert-butoxycarbonyl)amino]-4-fluoro-6-methylhept-3-enoyl (S)-sultam (919121-03-2) → 2-benzyl-5-tert-butoxycarbonylamino-4-fluoro-6-methyl-hept-3-enoic acid (919121-10-1)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; at 0 ℃; for 1h;

DOI:10.1039/b608596b

Reference yield:

(5S,2E)-5-[N-(tert-butoxycarbonyl)amino]-4,4-difluoro-6-methylhept-2-enoyl (S)-sultam (919120-99-3) → 2-benzyl-5-tert-butoxycarbonylamino-4-fluoro-6-methyl-hept-3-enoic acid (919121-10-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / LiOH; H₂O₂ / tetrahydrofuran; H₂O / 1 h / 0 °C

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water;

DOI:10.1039/b608596b

Reference yield:

ethyl (3S)-4-methyl-3-(N-tert-butylcarbonyloxy)amino-2,2-difluoropentanoate (676460-38-1) → 2-benzyl-5-tert-butoxycarbonylamino-4-fluoro-6-methyl-hept-3-enoic acid (919121-10-1)

Guidance literature:

Multi-step reaction with 4 steps

1: DIBAl-H / -78 °C

2: LiCl; (iPr)2NEt

3: 75 percent / LiOH; H₂O₂ / tetrahydrofuran; H₂O / 1 h / 0 °C

With lithium hydroxide; dihydrogen peroxide; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; lithium chloride; In tetrahydrofuran; water; 2: Horner-Wadsworth-Emmons coupling;

DOI:10.1039/b608596b

upstream raw materials:

(2R,5S,3Z)-2-benzyl-5-[N-(tert-butoxycarbonyl)amino]-4-fluoro-6-methylhept-3-enoyl (S)-sultam

(5S,2E)-5-[N-(tert-butoxycarbonyl)amino]-4,4-difluoro-6-methylhept-2-enoyl (S)-sultam

ethyl (3S)-4-methyl-3-(N-tert-butylcarbonyloxy)amino-2,2-difluoropentanoate

Downstream raw materials:

methyl (2R,5S,3Z)-2-benzyl-5-[N-(tert-butoxycarbonyl)amino]-4-fluoro-6-methylhept-3-enoate

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