N-(benzyloxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactopyranosyl)serylalanylalanine

Base Information

Chemical Name:N-(benzyloxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactopyranosyl)serylalanylalanine
CAS No.:118398-58-6
Molecular Formula:C₃₁H₄₂N₄O₁₅
Molecular Weight:710.692
Hs Code.:

Synonyms:N-(benzyloxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactopyranosyl)serylalanylalanine

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Chemical Property of N-(benzyloxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactopyranosyl)serylalanylalanine

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Technology Process of N-(benzyloxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactopyranosyl)serylalanylalanine

There total 9 articles about N-(benzyloxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactopyranosyl)serylalanylalanine 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: 43.0%

: 118398-54-2
N-(benzyloxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactopyranosyl)serylalanylalanine allyl ester

: 118398-58-6
N-(benzyloxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactopyranosyl)serylalanylalanine

Guidance literature:: With morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; for 0.5h; Ambient temperature;
DOI:10.1021/jo00265a007

Reference yield:

: 1145-80-8
N-(benzyloxycarbonyl)-L-serine

: 118398-58-6
N-(benzyloxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactopyranosyl)serylalanylalanine

Guidance literature:: Multi-step reaction with 7 steps

1: 83 percent / NaHCO₃, tricaprylmethylammonium chloride / H₂O; CH₂Cl₂ / 72 h

3: glacial acetic acid / tetrahydrofuran / 2 h / 0 - 20 °C

4: pyridine / tetrahydrofuran / 0 °C

5: 89 percent / morpholine, tetrakis(triphenylphosphine)palladium⁽⁰⁾ / tetrahydrofuran / 0.5 h / Ambient temperature

6: 61 percent / triethylamine, ethyl 2-ethoxy-1,2-dihydroquinoline-1-carboxylate / CH₂Cl₂; CHCl₃ / 48 h / Ambient temperature

7: 43 percent / morpholine, tetrakis(triphenylphosphine)palladium⁽⁰⁾ / tetrahydrofuran / 0.5 h / Ambient temperature

With morpholine; pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Aliquat 336; sodium hydrogencarbonate; acetic acid; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; In tetrahydrofuran; dichloromethane; chloroform; water;
DOI:10.1021/jo00265a007

Reference yield:

: 88295-41-4
N-(benzyloxycarbonyl)serine allyl ester

: 118398-58-6
N-(benzyloxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactopyranosyl)serylalanylalanine

Guidance literature:: Multi-step reaction with 6 steps

2: glacial acetic acid / tetrahydrofuran / 2 h / 0 - 20 °C

3: pyridine / tetrahydrofuran / 0 °C

4: 89 percent / morpholine, tetrakis(triphenylphosphine)palladium⁽⁰⁾ / tetrahydrofuran / 0.5 h / Ambient temperature

5: 61 percent / triethylamine, ethyl 2-ethoxy-1,2-dihydroquinoline-1-carboxylate / CH₂Cl₂; CHCl₃ / 48 h / Ambient temperature

6: 43 percent / morpholine, tetrakis(triphenylphosphine)palladium⁽⁰⁾ / tetrahydrofuran / 0.5 h / Ambient temperature

With morpholine; pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; acetic acid; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; In tetrahydrofuran; dichloromethane; chloroform;
DOI:10.1021/jo00265a007