methyl (S)-N²-benzyloxycarbonyl-N⁶-tert-butoxycarbonyl-N⁴-phenylcarbamoyl-4-azalysinate

Base Information

• Chemical Name: methyl (S)-N²-benzyloxycarbonyl-N⁶-tert-butoxycarbonyl-N⁴-phenylcarbamoyl-4-azalysinate
• CAS No.: 439864-36-5
• Molecular Formula: C₂₆H₃₄N₄O₇
• Molecular Weight: 514.579

Synonyms:methyl (S)-N²-benzyloxycarbonyl-N⁶-tert-butoxycarbonyl-N⁴-phenylcarbamoyl-4-azalysinate

Chemical Property of methyl (S)-N²-benzyloxycarbonyl-N⁶-tert-butoxycarbonyl-N⁴-phenylcarbamoyl-4-azalysinate

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Technology Process of methyl (S)-N²-benzyloxycarbonyl-N⁶-tert-butoxycarbonyl-N⁴-phenylcarbamoyl-4-azalysinate

There total 10 articles about methyl (S)-N²-benzyloxycarbonyl-N⁶-tert-butoxycarbonyl-N⁴-phenylcarbamoyl-4-azalysinate 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: 69.0%

phenyl isocyanate (103-71-9) + methyl N2-benzyloxycarbonyl-N6-tert-butoxycarbonyl-2(S),6-diamino-4-azahexanoate (239789-53-8) → methyl (S)-N2-benzyloxycarbonyl-N6-tert-butoxycarbonyl-N4-phenylcarbamoyl-4-azalysinate (439864-36-5)

Guidance literature:

In diethyl ether; at 20 ℃; for 5h;

DOI:10.1021/jo010456e

Reference yield:

N-benzyloxycarbonyl-L-asparagine (2304-96-3) → methyl (S)-N2-benzyloxycarbonyl-N6-tert-butoxycarbonyl-N4-phenylcarbamoyl-4-azalysinate (439864-36-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 89 percent / iodosobenzene diacetate / ethyl acetate; acetonitrile; H₂O / 4.5 h / 15 - 20 °C

2: 78 percent / HCl / 5 °C

3: 65 percent / acetic acid; sodium cyanoborohydride / methanol

4: 69 percent / diethyl ether / 5 h / 20 °C

With hydrogenchloride; [bis(acetoxy)iodo]benzene; sodium cyanoborohydride; acetic acid; In methanol; diethyl ether; water; ethyl acetate; acetonitrile;

DOI:10.1021/jo010456e

Reference yield:

N-(t-butoxycarbonyl)glycinal (89711-08-0) → methyl (S)-N2-benzyloxycarbonyl-N6-tert-butoxycarbonyl-N4-phenylcarbamoyl-4-azalysinate (439864-36-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / acetic acid; sodium cyanoborohydride / methanol

2: 69 percent / diethyl ether / 5 h / 20 °C

With sodium cyanoborohydride; acetic acid; In methanol; diethyl ether;

DOI:10.1021/jo010456e

upstream raw materials:

phenyl isocyanate

methyl N²-benzyloxycarbonyl-N⁶-tert-butoxycarbonyl-2(S),6-diamino-4-azahexanoate

di-tert-butyl dicarbonate

2-(N-tert-butoxycarbonylamino)ethanol

Downstream raw materials:

(S)-N²-9-fluorenylmethoxycarbonyl-N⁶-tert-butoxycarbonyl-N⁴-phenylcarbamoyl-4-azalysine

(S)-N⁶-tert-butoxycarbonyl-N⁴-phenylcarbamoyl-4-azalysine

(S)-N²-benzyloxycarbonyl-N⁶-tertbutoxycarbonyl-N⁴-phenylcarbamoyl-4-azalysine

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