(S)-3-[4-(2-Azido-ethoxy)-3-nitro-benzoylamino]-2-(naphthalene-1-sulfonylamino)-propionic acid benzyl ester

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Chemical Name:(S)-3-[4-(2-Azido-ethoxy)-3-nitro-benzoylamino]-2-(naphthalene-1-sulfonylamino)-propionic acid benzyl ester
CAS No.:215050-33-2
Molecular Formula:C₂₉H₂₆N₆O₈S
Molecular Weight:618.627
Hs Code.:

Synonyms:(S)-3-[4-(2-Azido-ethoxy)-3-nitro-benzoylamino]-2-(naphthalene-1-sulfonylamino)-propionic acid benzyl ester

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Chemical Property of (S)-3-[4-(2-Azido-ethoxy)-3-nitro-benzoylamino]-2-(naphthalene-1-sulfonylamino)-propionic acid benzyl ester

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Technology Process of (S)-3-[4-(2-Azido-ethoxy)-3-nitro-benzoylamino]-2-(naphthalene-1-sulfonylamino)-propionic acid benzyl ester

There total 8 articles about (S)-3-[4-(2-Azido-ethoxy)-3-nitro-benzoylamino]-2-(naphthalene-1-sulfonylamino)-propionic acid benzyl ester 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: 57.0%

: 85-46-1
1-Naphthalenesulfonyl chloride

: 215050-05-8
(S)-2-Amino-3-[4-(2-azido-ethoxy)-3-nitro-benzoylamino]-propionic acid benzyl ester

: 215050-33-2
(S)-3-[4-(2-Azido-ethoxy)-3-nitro-benzoylamino]-2-(naphthalene-1-sulfonylamino)-propionic acid benzyl ester

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 25 ℃; for 4h;
DOI:10.1016/S0968-0896(98)00090-X

Reference yield:

: 453-71-4
3-nitro-4-fluorobenzoic acid

: 215050-33-2
(S)-3-[4-(2-Azido-ethoxy)-3-nitro-benzoylamino]-2-(naphthalene-1-sulfonylamino)-propionic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 98 percent / toluene / 8 h / 80 °C

2: 73 percent / molecular sieves 4A / Bu₄NF / dimethylformamide / 4 h / 25 °C

3: 99 percent / LiOH*H₂O / H₂O; dioxane / 4 h / 25 °C

4: 82 percent / DCC / 4-DMAP / CH₂Cl₂ / 4 h / 25 °C

5: 84 percent / CF₃CO₂H / CH₂Cl₂ / 2 h / 25 °C / Acid hydrolysis

6: 57 percent / i-Pr₂NEt / CH₂Cl₂ / 4 h / 25 °C

With lithium hydroxide; 4 A molecular sieve; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; dmap; tetrabutyl ammonium fluoride; In 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1: Esterification / 2: Substitution / 3: Hydrolysis / 4: Substitution / 5: Hydrolysis / 6: Substitution;
DOI:10.1016/S0968-0896(98)00090-X

Reference yield:

: 13512-57-7
N-[(1,1-dimethylethoxycarbonyl)amino]-L-asparagine benzyl ester

: 215050-33-2
(S)-3-[4-(2-Azido-ethoxy)-3-nitro-benzoylamino]-2-(naphthalene-1-sulfonylamino)-propionic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 41 percent / PhI(OCOCF₃)2; pyridine / dimethylformamide; H₂O / 3.5 h / 25 °C

2: 82 percent / DCC / 4-DMAP / CH₂Cl₂ / 4 h / 25 °C

3: 84 percent / CF₃CO₂H / CH₂Cl₂ / 2 h / 25 °C / Acid hydrolysis

4: 57 percent / i-Pr₂NEt / CH₂Cl₂ / 4 h / 25 °C

With pyridine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; bis-[(trifluoroacetoxy)iodo]benzene; dmap; In dichloromethane; water; N,N-dimethyl-formamide; 1: Reduction / 2: Substitution / 3: Hydrolysis / 4: Substitution;
DOI:10.1016/S0968-0896(98)00090-X