N-[2-bis[(benzyloxycarbonyl)methyl]aminoethyl]-N-[(2S,4S)-4-[2-(benzyloxycarbonyl)-1-[(benzyloxycarbonyl)methyl]pyrrolidinyl]]-D-serine benzyl ester

Base Information

Chemical Name:N-[2-bis[(benzyloxycarbonyl)methyl]aminoethyl]-N-[(2S,4S)-4-[2-(benzyloxycarbonyl)-1-[(benzyloxycarbonyl)methyl]pyrrolidinyl]]-D-serine benzyl ester
CAS No.:288582-39-8
Molecular Formula:C₅₁H₅₅N₃O₁₁
Molecular Weight:886.011
Hs Code.:

N-[2-bis[(benzyloxycarbonyl)methyl]aminoethyl]-N-[(2S,4S)-4-[2-(benzyloxycarbonyl)-1-[(benzyloxycarbonyl)methyl]pyrrolidinyl]]-D-serine benzyl ester

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Chemical Property of N-[2-bis[(benzyloxycarbonyl)methyl]aminoethyl]-N-[(2S,4S)-4-[2-(benzyloxycarbonyl)-1-[(benzyloxycarbonyl)methyl]pyrrolidinyl]]-D-serine benzyl ester

Chemical Property:

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Technology Process of N-[2-bis[(benzyloxycarbonyl)methyl]aminoethyl]-N-[(2S,4S)-4-[2-(benzyloxycarbonyl)-1-[(benzyloxycarbonyl)methyl]pyrrolidinyl]]-D-serine benzyl ester

There total 6 articles about N-[2-bis[(benzyloxycarbonyl)methyl]aminoethyl]-N-[(2S,4S)-4-[2-(benzyloxycarbonyl)-1-[(benzyloxycarbonyl)methyl]pyrrolidinyl]]-D-serine 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:

: (2S,4S)-4-{((R)-1-Benzyloxycarbonyl-2-hydroxy-ethyl)-[2-(bis-benzyloxycarbonylmethyl-amino)-ethyl]-amino}-pyrrolidine-2-carboxylic acid benzyl ester

: 5437-45-6
Benzyl bromoacetate

: 288582-39-8
N-[2-bis[(benzyloxycarbonyl)methyl]aminoethyl]-N-[(2S,4S)-4-[2-(benzyloxycarbonyl)-1-[(benzyloxycarbonyl)methyl]pyrrolidinyl]]-D-serine benzyl ester

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 0 - 20 ℃;
DOI:10.1021/jo000071g

Reference yield:

: 133099-79-3
D-serine benzyl ester

: 288582-39-8
N-[2-bis[(benzyloxycarbonyl)methyl]aminoethyl]-N-[(2S,4S)-4-[2-(benzyloxycarbonyl)-1-[(benzyloxycarbonyl)methyl]pyrrolidinyl]]-D-serine benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: diisopropylethylamine; (CF₃SO₂)2O / CH₂Cl₂ / 0.75 h / -20 °C

1.2: 68 percent / diisopropylethylamine / CH₂Cl₂ / -20 - -8 °C

2.1: 27 percent / phosphate buffer / acetonitrile; H₂O / pH 8 / Heating

3.1: CF₃COOH / CH₂Cl₂ / 20 °C

4.1: diisopropylethylamine / tetrahydrofuran / 0 - 20 °C

With phosphate buffer; trifluoromethylsulfonic anhydride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; acetonitrile; 1.1: sulfonation / 1.2: Substitution / 2.1: Alkylation / 3.1: carbamate cleavage / 4.1: Alkylation;
DOI:10.1021/jo000071g

Reference yield:

: 89813-47-8
N-(tert-butoxycarbonyl)-(2S,4R)-4-hydroxyproline benzyl ester

: 288582-39-8
N-[2-bis[(benzyloxycarbonyl)methyl]aminoethyl]-N-[(2S,4S)-4-[2-(benzyloxycarbonyl)-1-[(benzyloxycarbonyl)methyl]pyrrolidinyl]]-D-serine benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: diisopropylethylamine; (CF₃SO₂)2O / CH₂Cl₂ / 0.75 h / -20 °C

1.2: 68 percent / diisopropylethylamine / CH₂Cl₂ / -20 - -8 °C

2.1: 27 percent / phosphate buffer / acetonitrile; H₂O / pH 8 / Heating

3.1: CF₃COOH / CH₂Cl₂ / 20 °C

4.1: diisopropylethylamine / tetrahydrofuran / 0 - 20 °C

With phosphate buffer; trifluoromethylsulfonic anhydride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; acetonitrile; 1.1: sulfonation / 1.2: Substitution / 2.1: Alkylation / 3.1: carbamate cleavage / 4.1: Alkylation;
DOI:10.1021/jo000071g