N^a-(9-fluorenylmethoxycarbonyl)-N^im-(triphenylmethyl)-(S)-erythro-3-hydroxyhistidine

Base Information

• Chemical Name: N^a-(9-fluorenylmethoxycarbonyl)-N^im-(triphenylmethyl)-(S)-erythro-3-hydroxyhistidine
• CAS No.: 308849-84-5
• Molecular Formula: C₄₀H₃₃N₃O₅
• Molecular Weight: 635.719

Synonyms:N^a-(9-fluorenylmethoxycarbonyl)-N^im-(triphenylmethyl)-(S)-erythro-3-hydroxyhistidine

Chemical Property of N^a-(9-fluorenylmethoxycarbonyl)-N^im-(triphenylmethyl)-(S)-erythro-3-hydroxyhistidine

Chemical Property:

Purity/Quality:

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Technology Process of N^a-(9-fluorenylmethoxycarbonyl)-N^im-(triphenylmethyl)-(S)-erythro-3-hydroxyhistidine

There total 2 articles about N^a-(9-fluorenylmethoxycarbonyl)-N^im-(triphenylmethyl)-(S)-erythro-3-hydroxyhistidine 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:

(2'S,3'R,4R)-3-[2'-azido-3'-hydroxy-3'-(N-(triphenylmethyl)imidazol-4''-yl)propanoyl]-4-isopropyl-2-oxazolidinone (121895-46-3) → Na-(9-fluorenylmethoxycarbonyl)-Nim-(triphenylmethyl)-(S)-erythro-3-hydroxyhistidine (308849-84-5)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. LiOH / tetrahydrofuran / 0.67 h / 25 °C

2: 0.56 g / H₂; aq. K₂CO₃ / 10percent Pd/C / tetrahydrofuran / 16 h

With lithium hydroxide; hydrogen; potassium carbonate; 10percent Pd/C; In tetrahydrofuran;

DOI:10.1021/ja011820u

Reference yield:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + (2S,3R)-2-Azido-3-hydroxy-3-(1-trityl-1H-imidazol-4-yl)-propionic acid → Na-(9-fluorenylmethoxycarbonyl)-Nim-(triphenylmethyl)-(S)-erythro-3-hydroxyhistidine (308849-84-5)

Guidance literature:

With hydrogen; potassium carbonate; 10percent Pd/C; In tetrahydrofuran; for 16h;

DOI:10.1021/ja011820u

Reference yield: 69.0%

benzylamine (100-46-9) + Na-(9-fluorenylmethoxycarbonyl)-Nim-(triphenylmethyl)-(S)-erythro-3-hydroxyhistidine (308849-84-5) → O-benzyl-Na-(9-fluorenylmethoxycarbonyl)-Nim-(triphenylmethyl)-(S)-erythro-3-hydroxyhistidine (477335-39-0)

Guidance literature:

In ethyl acetate; at 20 ℃; for 3h;

DOI:10.1021/ja0208916

upstream raw materials:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(2'S,3'R,4R)-3-[2'-azido-3'-hydroxy-3'-(N-(triphenylmethyl)imidazol-4''-yl)propanoyl]-4-isopropyl-2-oxazolidinone

Downstream raw materials:

O-benzyl-N^a-(9-fluorenylmethoxycarbonyl)-N^im-(triphenylmethyl)-(S)-erythro-3-hydroxyhistidine

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