N^α-(9-fluorenylmethyloxycarbonyl)-N^γ-(2-chlorobenzyloxycarbonyl)-L-α,γ-diaminobutyric acid

Base Information

• Chemical Name: N^α-(9-fluorenylmethyloxycarbonyl)-N^γ-(2-chlorobenzyloxycarbonyl)-L-α,γ-diaminobutyric acid
• CAS No.: 811434-05-6
• Molecular Formula: C₂₇H₂₅ClN₂O₆
• Molecular Weight: 508.958

Synonyms:N^α-(9-fluorenylmethyloxycarbonyl)-N^γ-(2-chlorobenzyloxycarbonyl)-L-α,γ-diaminobutyric acid

Chemical Property of N^α-(9-fluorenylmethyloxycarbonyl)-N^γ-(2-chlorobenzyloxycarbonyl)-L-α,γ-diaminobutyric acid

Chemical Property:

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Technology Process of N^α-(9-fluorenylmethyloxycarbonyl)-N^γ-(2-chlorobenzyloxycarbonyl)-L-α,γ-diaminobutyric acid

There total 2 articles about N^α-(9-fluorenylmethyloxycarbonyl)-N^γ-(2-chlorobenzyloxycarbonyl)-L-α,γ-diaminobutyric acid 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: 85.7%

2-chlorobenzyloxycarbonyl-N-hydroxysuccinimide (65853-65-8) + Nα-(9-fluorenylmethoxycarbonyl)-L-2,4-diaminobutyric acid (161420-87-7,201484-12-0) → Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-(2-chlorobenzyloxycarbonyl)-L-α,γ-diaminobutyric acid (811434-05-6)

Guidance literature:

With triethylamine; In water; dimethyl sulfoxide; at 20 ℃; for 3h;

DOI:10.1246/bcsj.77.1915

Reference yield:

N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamine (71989-20-3) → Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-(2-chlorobenzyloxycarbonyl)-L-α,γ-diaminobutyric acid (811434-05-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 88.9 percent / I,I-bis(trifluoroacetoxy)iodobenzene; H₂O / dimethylsulfoxide / 20 h

2: 85.7 percent / triethylamine / H₂O; dimethylsulfoxide / 3 h / 20 °C

With water; triethylamine; bis-[(trifluoroacetoxy)iodo]benzene; In water; dimethyl sulfoxide; 1: Hofmann rearrangement;

DOI:10.1246/bcsj.77.1915

Reference yield:

Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-(2-chlorobenzyloxycarbonyl)-L-α,γ-diaminobutyric acid (811434-05-6) + Fmoc-Thr(Bzl)-O-HMP-resin + Fmoc-Leu-OH (35661-60-0) + Fmoc-D-Phe-OH (86123-10-6) + (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid (125238-99-5,114360-56-4) + (2S,3R)-Fmoc-O-benzyl-threonine (117872-75-0) → Fmoc-L-α,γ-diaminobutyryl(2-ClZ)-Thr(Bzl)-L-α,γ-diaminobutyryl(2-ClZ)-L-α,γ-diaminobutyryl-L-α,γ-diaminobutyryl(2-ClZ)-d-Phe-Leu-L-α,γ-diaminobutyryl(2-ClZ)-L-α,γ-diaminobutyryl(2-ClZ)-Thr(Bzl)-OH

Guidance literature:

N^α-(9-fluorenylmethyloxycarbonyl)-N^γ-(2-chlorobenzyloxycarbonyl)-L-α,γ-diaminobutyric acid; Fmoc-Thr(Bzl)-O-HMP-resin; With N-[(dimethylamino)(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy)methylidene]-N-methylmethanaminium hexafluorophosphate; solid phase reaction;

With trifluoroacetic acid; In water; at 20 ℃; for 1h;

Fmoc-Leu-OH; Fmoc-D-Phe-OH; (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid; (2S,3R)-Fmoc-O-benzyl-threonine; Further stages;

DOI:10.1248/cpb.59.597

upstream raw materials:

2-chlorobenzyloxycarbonyl-N-hydroxysuccinimide

N_α-(9-fluorenylmethoxycarbonyl)-L-2,4-diaminobutyric acid

N₂-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamine

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