N^α-benzyloxycarbonyl-β-(2,2,5,7,8-pentamethylchroman-6-sulfonyl)guanidino-L-α-alanine

Base Information

• Chemical Name: N^α-benzyloxycarbonyl-β-(2,2,5,7,8-pentamethylchroman-6-sulfonyl)guanidino-L-α-alanine
• CAS No.: 281666-50-0
• Molecular Formula: C₂₆H₃₄N₄O₇S
• Molecular Weight: 546.645

Synonyms:N^α-benzyloxycarbonyl-β-(2,2,5,7,8-pentamethylchroman-6-sulfonyl)guanidino-L-α-alanine

Chemical Property of N^α-benzyloxycarbonyl-β-(2,2,5,7,8-pentamethylchroman-6-sulfonyl)guanidino-L-α-alanine

Chemical Property:

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Technology Process of N^α-benzyloxycarbonyl-β-(2,2,5,7,8-pentamethylchroman-6-sulfonyl)guanidino-L-α-alanine

There total 3 articles about N^α-benzyloxycarbonyl-β-(2,2,5,7,8-pentamethylchroman-6-sulfonyl)guanidino-L-α-alanine 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: 52.0%

2,2,5,7,8-pentamethylchroman-6-sulfonyl chloride (112160-39-1) + Nα-benzyloxycarbonyl-β-guanidino-L-α-alanine (281666-49-7) → Nα-benzyloxycarbonyl-β-(2,2,5,7,8-pentamethylchroman-6-sulfonyl)guanidino-L-α-alanine (281666-50-0)

Guidance literature:

With sodium hydroxide; In acetone; at 0 - 20 ℃; for 4h;

DOI:10.1016/S0040-4020(00)00123-X

Reference yield:

N-benzyloxycarbonyl-L-asparagine (2304-96-3) → Nα-benzyloxycarbonyl-β-(2,2,5,7,8-pentamethylchroman-6-sulfonyl)guanidino-L-α-alanine (281666-50-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 47 percent / [bis(trifluoroacetoxy)iodo]-benzene; pyridine / dimethylformamide; H₂O / 4.5 h / 20 °C

2: 40 percent / Na₂CO₃ / H₂O / 20 °C

3: 52 percent / NaOH / acetone / 4 h / 0 - 20 °C

With pyridine; sodium hydroxide; sodium carbonate; bis-[(trifluoroacetoxy)iodo]benzene; In water; N,N-dimethyl-formamide; acetone; 1: Decarbonylation / 2: Substitution / 3: Substitution;

DOI:10.1016/S0040-4020(00)00123-X

Reference yield:

(S)-3-amino-2-(((benzyloxy)carbonyl)amino)propanoic acid (35761-26-3) → Nα-benzyloxycarbonyl-β-(2,2,5,7,8-pentamethylchroman-6-sulfonyl)guanidino-L-α-alanine (281666-50-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 40 percent / Na₂CO₃ / H₂O / 20 °C

2: 52 percent / NaOH / acetone / 4 h / 0 - 20 °C

With sodium hydroxide; sodium carbonate; In water; acetone; 1: Substitution / 2: Substitution;

DOI:10.1016/S0040-4020(00)00123-X

upstream raw materials:

2,2,5,7,8-pentamethylchroman-6-sulfonyl chloride

N^α-benzyloxycarbonyl-β-guanidino-L-α-alanine

N-benzyloxycarbonyl-L-asparagine

(S)-3-amino-2-(((benzyloxy)carbonyl)amino)propanoic acid

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