(N-(3-benzyloxypyridyl-2-carbonyl)-D-Ser-Pip-Gly-Sar-NMe-Val)2 (serine hydroxyl) dilactone

Base Information

• Chemical Name: (N-(3-benzyloxypyridyl-2-carbonyl)-D-Ser-Pip-Gly-Sar-NMe-Val)2 (serine hydroxyl) dilactone
• CAS No.: 203807-29-8
• Molecular Formula: C₆₆H₈₄N₁₂O₁₆
• Molecular Weight: 1301.46
• Mol file: 203807-29-8.mol

Synonyms:(N-(3-benzyloxypyridyl-2-carbonyl)-D-Ser-Pip-Gly-Sar-NMe-Val)2 (serine hydroxyl) dilactone

Chemical Property of (N-(3-benzyloxypyridyl-2-carbonyl)-D-Ser-Pip-Gly-Sar-NMe-Val)2 (serine hydroxyl) dilactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (N-(3-benzyloxypyridyl-2-carbonyl)-D-Ser-Pip-Gly-Sar-NMe-Val)2 (serine hydroxyl) dilactone

There total 4 articles about (N-(3-benzyloxypyridyl-2-carbonyl)-D-Ser-Pip-Gly-Sar-NMe-Val)2 (serine hydroxyl) dilactone 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: 85.0%

3-benzyloxypyridine-2-carboxylic acid (117523-29-2) + (3R,7S,16S,23R,27S,36S)-3,23-Diamino-7,27-diisopropyl-8,11,28,31-tetramethyl-5,25-dioxa-1,8,11,14,21,28,31,34-octaaza-tricyclo[34.4.0.016,21]tetracontane-2,6,9,12,15,22,26,29,32,35-decaone; hydrochloride → (N-(3-benzyloxypyridyl-2-carbonyl)-D-Ser-Pip-Gly-Sar-NMe-Val)2 (serine hydroxyl) dilactone (203807-29-8)

Guidance literature:

With sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 25 ℃;

DOI:10.1016/S0968-0896(97)10014-1

Reference yield:

3-hydroxypyridine-2-carboxylic acid (874-24-8) → (N-(3-benzyloxypyridyl-2-carbonyl)-D-Ser-Pip-Gly-Sar-NMe-Val)2 (serine hydroxyl) dilactone (203807-29-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / K₂CO₃ / dimethylformamide / 4 h / 25 °C

2: 95 percent / LiOH / tetrahydrofuran; methanol; H₂O / 25 °C

3: 85 percent / NaHCO₃; HOBt; EDCI / dimethylformamide / 25 °C

With lithium hydroxide; sodium hydrogencarbonate; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; 1: Alkylation / 2: Hydrolysis / 3: Condensation;

DOI:10.1016/S0968-0896(97)10014-1

Reference yield:

(N-Boc-D-Ser-Pip-Gly-Sar-NMe-Val)2(serine hydroxyl) dilactone (151961-28-3) → (N-(3-benzyloxypyridyl-2-carbonyl)-D-Ser-Pip-Gly-Sar-NMe-Val)2 (serine hydroxyl) dilactone (203807-29-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / HCl / ethyl acetate / 0.5 h / 25 °C

2: 85 percent / NaHCO₃; HOBt; EDCI / dimethylformamide / 25 °C

With hydrogenchloride; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In ethyl acetate; N,N-dimethyl-formamide; 1: deprotection / 2: Condensation;

DOI:10.1016/S0968-0896(97)10014-1

upstream raw materials:

3-benzyloxypyridine-2-carboxylic acid

3-hydroxypyridine-2-carboxylic acid

(N-Boc-D-Ser-Pip-Gly-Sar-NMe-Val)2(serine hydroxyl) dilactone

3-benzyloxypyridine-2-carboxylic acid benzyl ester