2-<2-(1,3-dioxolan-2-yl)ethyl>-2-<1(S)-<ε-(benzyloxycarbonyl)-N^α-(cyclobutylcarbonyl)-L-lysyl>amino>-2-phenylethyl>-1,3-dioxolane

Base Information

• Chemical Name: 2-<2-(1,3-dioxolan-2-yl)ethyl>-2-<1(S)-<ε-(benzyloxycarbonyl)-N^α-(cyclobutylcarbonyl)-L-lysyl>amino>-2-phenylethyl>-1,3-dioxolane
• CAS No.: 96792-08-4
• Molecular Formula: C₃₅H₄₇N₃O₈
• Molecular Weight: 637.773

Synonyms:2-<2-(1,3-dioxolan-2-yl)ethyl>-2-<1(S)-<ε-(benzyloxycarbonyl)-N^α-(cyclobutylcarbonyl)-L-lysyl>amino>-2-phenylethyl>-1,3-dioxolane

Chemical Property of 2-<2-(1,3-dioxolan-2-yl)ethyl>-2-<1(S)-<ε-(benzyloxycarbonyl)-N^α-(cyclobutylcarbonyl)-L-lysyl>amino>-2-phenylethyl>-1,3-dioxolane

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Technology Process of 2-<2-(1,3-dioxolan-2-yl)ethyl>-2-<1(S)-<ε-(benzyloxycarbonyl)-N^α-(cyclobutylcarbonyl)-L-lysyl>amino>-2-phenylethyl>-1,3-dioxolane

There total 4 articles about 2-<2-(1,3-dioxolan-2-yl)ethyl>-2-<1(S)-<ε-(benzyloxycarbonyl)-N^α-(cyclobutylcarbonyl)-L-lysyl>amino>-2-phenylethyl>-1,3-dioxolane 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: 86.0%

(S)-1-[4-(2-[1,3]Dioxolan-2-yl-ethyl)-[1,3]dioxolan-4-yl]-2-phenyl-ethylamine + N2-(Cyclobutylcarbonyl)-N6-[(phenylmethoxy)-carbonyl]-L-lysine (96867-10-6) → 2-<2-(1,3-dioxolan-2-yl)ethyl>-2-<1(S)-<ε-(benzyloxycarbonyl)-Nα-(cyclobutylcarbonyl)-L-lysyl>amino>-2-phenylethyl>-1,3-dioxolane (96792-08-4)

Guidance literature:

With 1-hydroxybenzotriazol-hydrate; dicyclohexyl-carbodiimide; In dichloromethane; for 64h; Ambient temperature;

DOI:10.1021/jm00146a014

Reference yield:

(S)-methyl 2-amino-6-(benzyloxycarbonylamino)hexanoate (24498-31-5) → 2-<2-(1,3-dioxolan-2-yl)ethyl>-2-<1(S)-<ε-(benzyloxycarbonyl)-Nα-(cyclobutylcarbonyl)-L-lysyl>amino>-2-phenylethyl>-1,3-dioxolane (96792-08-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 84.4 percent / Et₃N / CH₂Cl₂ / a) 0 deg C, 1 h, b) RT, 2 h

2: 93.2 percent / 1N NaOH / methanol / a) 0 deg C, 1 h, b) RT, 64 h

3: 86 percent / 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide / CH₂Cl₂ / 64 h / Ambient temperature

With sodium hydroxide; 1-hydroxybenzotriazol-hydrate; triethylamine; dicyclohexyl-carbodiimide; In methanol; dichloromethane;

DOI:10.1021/jm00146a014

Reference yield:

Nε-(benzyloxycarbonyl)-Nα-(cyclobutylcarbonyl)-L-lysine methyl ester (96867-09-3) → 2-<2-(1,3-dioxolan-2-yl)ethyl>-2-<1(S)-<ε-(benzyloxycarbonyl)-Nα-(cyclobutylcarbonyl)-L-lysyl>amino>-2-phenylethyl>-1,3-dioxolane (96792-08-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 93.2 percent / 1N NaOH / methanol / a) 0 deg C, 1 h, b) RT, 64 h

2: 86 percent / 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide / CH₂Cl₂ / 64 h / Ambient temperature

With sodium hydroxide; 1-hydroxybenzotriazol-hydrate; dicyclohexyl-carbodiimide; In methanol; dichloromethane;

DOI:10.1021/jm00146a014

upstream raw materials:

N₂-(Cyclobutylcarbonyl)-N₆-[(phenylmethoxy)-carbonyl]-L-lysine

(S)-methyl 2-amino-6-(benzyloxycarbonylamino)hexanoate

N^ε-(benzyloxycarbonyl)-N^α-(cyclobutylcarbonyl)-L-lysine methyl ester

Cyclobutanecarbonyl chloride

Downstream raw materials:

5(S)-<ε-(butyloxycarbonyl)-N^α-(cyclobutylcarbonyl)-L-lysyl>amino>-4-oxo-6-phenylhexanoyl-L-proline hydroxylamide

succinimidyl 5(S)-<ε-(butyloxycarbonyl)-N^α-(cyclobutylcarbonyl)-L-lysyl>amino>-4-oxo-6-phenylhexanoate

5(S)-<α-(cyclobutylcarbonyl)-L-lysyl>amino>-4-oxo-6-phenylhexanoyl-L-proline hydroxylamide

2-(2-carboxyethyl)-2-<1(S)-<ε-(benzyloxycarbonyl)-N^α-(cyclobutylcarbonyl)-L-lysyl>amino>-2-phenylethyl>-1,3-dioxolane

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