(S)-N-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-N'-[2-(9-fluorenylmethoxycarbonyl)amino-4-phenylbutylcarbonyl]methylisothiourea

Base Information

• Chemical Name: (S)-N-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-N'-[2-(9-fluorenylmethoxycarbonyl)amino-4-phenylbutylcarbonyl]methylisothiourea
• CAS No.: 535952-65-9
• Molecular Formula: C₄₂H₄₇N₃O₁₂S
• Molecular Weight: 817.914
• Mol file: 535952-65-9.mol

Synonyms:(S)-N-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-N'-[2-(9-fluorenylmethoxycarbonyl)amino-4-phenylbutylcarbonyl]methylisothiourea

Chemical Property of (S)-N-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-N'-[2-(9-fluorenylmethoxycarbonyl)amino-4-phenylbutylcarbonyl]methylisothiourea

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-N-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-N'-[2-(9-fluorenylmethoxycarbonyl)amino-4-phenylbutylcarbonyl]methylisothiourea

There total 2 articles about (S)-N-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-N'-[2-(9-fluorenylmethoxycarbonyl)amino-4-phenylbutylcarbonyl]methylisothiourea 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: 67.0%

(S)-3-(<<(9H-fluoren-9-yl)methoxy>carbonyl>amino)-5-phenylpentanoic acid (219967-74-5) + N-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)methylisothiourea (535952-60-4) → (S)-N-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-N'-[2-(9-fluorenylmethoxycarbonyl)amino-4-phenylbutylcarbonyl]methylisothiourea (535952-65-9)

Guidance literature:

With i-PrNEt; benzotriazol-1-ol; diisopropyl-carbodiimide; In dichloromethane; N,N-dimethyl acetamide; at 20 ℃; for 24h;

DOI:10.1055/s-2003-36815

Reference yield:

N-(2,3,4,6-tetra-O-acetyl-D-glucopyranosyl)-N,N'-bis(tert-butoxycarbonyl)methylisothiourea → (S)-N-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-N'-[2-(9-fluorenylmethoxycarbonyl)amino-4-phenylbutylcarbonyl]methylisothiourea (535952-65-9)

Guidance literature:

Multi-step reaction with 2 steps

1: anisole; TFA / CH₂Cl₂ / 0.25 h / 0 °C

2: 67 percent / N-hydroxybenzotriazole; 1,3-diisopropylcarbodiimide; i-PrNEt / N,N-dimethyl-acetamide; CH₂Cl₂ / 24 h / 20 °C

With i-PrNEt; benzotriazol-1-ol; methoxybenzene; trifluoroacetic acid; diisopropyl-carbodiimide; In dichloromethane; N,N-dimethyl acetamide;

DOI:10.1055/s-2003-36815

Reference yield: 56.0%

(S)-N-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-N'-[2-(9-fluorenylmethoxycarbonyl)amino-4-phenylbutylcarbonyl]methylisothiourea (535952-65-9) → (S)-2-(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl)amino-6-ethylphenyl-5,6-dihydro-4-pyrimidinone

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1055/s-2003-36815

upstream raw materials:

(S)-3-(<<(9H-fluoren-9-yl)methoxy>carbonyl>amino)-5-phenylpentanoic acid

N-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)methylisothiourea