(S)-N²-benzyloxycarbonyl-N⁶-tert-butoxycarbonyl-N⁴-cyclohexylcarbamoyl-4-azalysine

Base Information

• Chemical Name: (S)-N²-benzyloxycarbonyl-N⁶-tert-butoxycarbonyl-N⁴-cyclohexylcarbamoyl-4-azalysine
• CAS No.: 439864-42-3
• Molecular Formula: C₂₅H₃₈N₄O₇
• Molecular Weight: 506.599

Synonyms:(S)-N²-benzyloxycarbonyl-N⁶-tert-butoxycarbonyl-N⁴-cyclohexylcarbamoyl-4-azalysine

Chemical Property of (S)-N²-benzyloxycarbonyl-N⁶-tert-butoxycarbonyl-N⁴-cyclohexylcarbamoyl-4-azalysine

Chemical Property:

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Technology Process of (S)-N²-benzyloxycarbonyl-N⁶-tert-butoxycarbonyl-N⁴-cyclohexylcarbamoyl-4-azalysine

There total 11 articles about (S)-N²-benzyloxycarbonyl-N⁶-tert-butoxycarbonyl-N⁴-cyclohexylcarbamoyl-4-azalysine 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: 70.0%

methyl (S)-N2-benzyloxycarbonyl-N6-tert-butoxycarbonyl-N4-cyclohexylcarbamoyl-4-azalysinate (439864-35-4) → (S)-N2-benzyloxycarbonyl-N6-tert-butoxycarbonyl-N4-cyclohexylcarbamoyl-4-azalysine (439864-42-3)

Guidance literature:

With lithium hydroxide; In methanol; water; at 20 ℃;

DOI:10.1021/jo010456e

Reference yield:

N-benzyloxycarbonyl-L-asparagine (2304-96-3) → (S)-N2-benzyloxycarbonyl-N6-tert-butoxycarbonyl-N4-cyclohexylcarbamoyl-4-azalysine (439864-42-3)

Guidance literature:

Multi-step reaction with 5 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: 79 percent / diethyl ether / 5 h / 20 °C

5: 70 percent / LiOH / H₂O; methanol / 20 °C

With hydrogenchloride; lithium hydroxide; [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) → (S)-N2-benzyloxycarbonyl-N6-tert-butoxycarbonyl-N4-cyclohexylcarbamoyl-4-azalysine (439864-42-3)

Guidance literature:

Multi-step reaction with 3 steps

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

2: 79 percent / diethyl ether / 5 h / 20 °C

3: 70 percent / LiOH / H₂O; methanol / 20 °C

With lithium hydroxide; sodium cyanoborohydride; acetic acid; In methanol; diethyl ether; water;

DOI:10.1021/jo010456e

upstream raw materials:

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

di-tert-butyl dicarbonate

2-(N-tert-butoxycarbonylamino)ethanol

N-benzyloxycarbonyl-L-asparagine

Downstream raw materials:

N⁶-tert-butoxycarbonyl-N⁴-cyclohexylcarbamoyl-4-azalysine

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

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