N^α-[(5R,8RS)-8-tert-butyldimethylsilyloxy-2,6-dioxo-1-azaspiro[4.4]octyl]-L-phenylalanine benzyl ester

Base Information

• Chemical Name: N^α-[(5R,8RS)-8-tert-butyldimethylsilyloxy-2,6-dioxo-1-azaspiro[4.4]octyl]-L-phenylalanine benzyl ester
• CAS No.: 406478-99-7
• Molecular Formula: C₂₉H₃₈N₂O₅Si
• Molecular Weight: 522.717

Synonyms:N^α-[(5R,8RS)-8-tert-butyldimethylsilyloxy-2,6-dioxo-1-azaspiro[4.4]octyl]-L-phenylalanine benzyl ester

Chemical Property of N^α-[(5R,8RS)-8-tert-butyldimethylsilyloxy-2,6-dioxo-1-azaspiro[4.4]octyl]-L-phenylalanine benzyl ester

Chemical Property:

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Technology Process of N^α-[(5R,8RS)-8-tert-butyldimethylsilyloxy-2,6-dioxo-1-azaspiro[4.4]octyl]-L-phenylalanine benzyl ester

There total 5 articles about N^α-[(5R,8RS)-8-tert-butyldimethylsilyloxy-2,6-dioxo-1-azaspiro[4.4]octyl]-L-phenylalanine 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: 99.0%

t-butyldimethylsiyl triflate (69739-34-0) + Nα-[(5R,8RS)-8-hydroxy-2,6-dioxo-1-azaspiro[4.4]octyl]-L-phenylalanine benzyl ester (406478-98-6) → Nα-[(5R,8RS)-8-tert-butyldimethylsilyloxy-2,6-dioxo-1-azaspiro[4.4]octyl]-L-phenylalanine benzyl ester (406478-99-7)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 25 ℃; for 6h;

DOI:10.1016/S0968-0896(01)00287-5

Reference yield:

L-phenylalanine benzyl ester hydrochloride (2462-32-0) → Nα-[(5R,8RS)-8-tert-butyldimethylsilyloxy-2,6-dioxo-1-azaspiro[4.4]octyl]-L-phenylalanine benzyl ester (406478-99-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: HOBt; NEM; EDC / CH₂Cl₂ / 0.08 h / 0 °C

1.2: 100 percent / CH₂Cl₂ / 2 h / 25 °C

2.1: OsO₄ / tetrahydrofuran; H₂O / 0.08 h / 25 °C

2.2: 100 percent / NaIO₄ / tetrahydrofuran; H₂O / 5 h / 25 °C

3.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 6 h / 25 °C

With 2,6-dimethylpyridine; N-Ethylmaleimide; osmium(VIII) oxide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/S0968-0896(01)00287-5

Reference yield:

(R)-2-allyl-5-oxopyrrolidine-2-carboxylic acid (406478-96-4) → Nα-[(5R,8RS)-8-tert-butyldimethylsilyloxy-2,6-dioxo-1-azaspiro[4.4]octyl]-L-phenylalanine benzyl ester (406478-99-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: HOBt; NEM; EDC / CH₂Cl₂ / 0.08 h / 0 °C

1.2: 100 percent / CH₂Cl₂ / 2 h / 25 °C

2.1: OsO₄ / tetrahydrofuran; H₂O / 0.08 h / 25 °C

2.2: 100 percent / NaIO₄ / tetrahydrofuran; H₂O / 5 h / 25 °C

3.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 6 h / 25 °C

With 2,6-dimethylpyridine; N-Ethylmaleimide; osmium(VIII) oxide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/S0968-0896(01)00287-5

upstream raw materials:

t-butyldimethylsiyl triflate

N^α-[(5R,8RS)-8-hydroxy-2,6-dioxo-1-azaspiro[4.4]octyl]-L-phenylalanine benzyl ester

L-phenylalanine benzyl ester hydrochloride

(R)-2-allyl-5-oxopyrrolidine-2-carboxylic acid

Downstream raw materials:

N^α-[(5R,8RS)-8-tert-butyldimethylsilyloxy-2,6-dioxo-1-azaspiro[4.4]octyl]-L-phenylalanyl-L-prolinamide

(S)-1-[(S)-2-((R)-2,6-Dioxo-1,7-diaza-spiro[4.4]non-8-en-7-yl)-3-phenyl-propionyl]-pyrrolidine-2-carboxylic acid amide

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