(S)-1-((S)-3-Benzyloxycarbonyl-3-{[(S)-3-benzyloxycarbonyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-tert-butoxycarbonyl-amino}-propyl)-azetidine-2-carboxylic acid benzyl ester

Base Information

• Chemical Name: (S)-1-((S)-3-Benzyloxycarbonyl-3-{[(S)-3-benzyloxycarbonyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-tert-butoxycarbonyl-amino}-propyl)-azetidine-2-carboxylic acid benzyl ester
• CAS No.: 77856-47-4
• Molecular Formula: C₄₃H₅₄N₂O₁₀
• Molecular Weight: 758.909
• Mol file: 77856-47-4.mol

Synonyms:

Chemical Property of (S)-1-((S)-3-Benzyloxycarbonyl-3-{[(S)-3-benzyloxycarbonyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-tert-butoxycarbonyl-amino}-propyl)-azetidine-2-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-((S)-3-Benzyloxycarbonyl-3-{[(S)-3-benzyloxycarbonyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-tert-butoxycarbonyl-amino}-propyl)-azetidine-2-carboxylic acid benzyl ester

There total 9 articles about (S)-1-((S)-3-Benzyloxycarbonyl-3-{[(S)-3-benzyloxycarbonyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-tert-butoxycarbonyl-amino}-propyl)-azetidine-2-carboxylic acid 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: 59.0%

(S)-Azetidine-2-carboxylic acid benzyl ester; compound with trifluoro-acetic acid (77856-46-3) + (S)-2-{[(S)-3-Benzyloxycarbonyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-tert-butoxycarbonyl-amino}-4-oxo-butyric acid benzyl ester (77856-44-1,77881-92-6,79466-01-6,120964-21-8) → (S)-1-((S)-3-Benzyloxycarbonyl-3-{[(S)-3-benzyloxycarbonyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-tert-butoxycarbonyl-amino}-propyl)-azetidine-2-carboxylic acid benzyl ester (77856-47-4,77881-93-7,83680-33-5)

Guidance literature:

With sodium cyanoborohydride; In methanol; 1.) 0 deg C, 1 h, 2.) room temperature, 16 h;

DOI:10.1021/ja00399a046

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) → (S)-1-((S)-3-Benzyloxycarbonyl-3-{[(S)-3-benzyloxycarbonyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-tert-butoxycarbonyl-amino}-propyl)-azetidine-2-carboxylic acid benzyl ester (77856-47-4,77881-93-7,83680-33-5)

Guidance literature:

Multi-step reaction with 8 steps

1: p-TsOH / CH₂Cl₂ / 0.5 h / 0 °C

2: 84 percent / 1.) 2.5percent KOH, 2.) 18-crown-6 / 1.) THF, room temperature, 1 h, 2.) DMF-H₂O, room temperature, 6 h

3: 72 percent / pyridinium chlorochromate / CH₂Cl₂ / 2 h / Ambient temperature

4: 90 percent / NaBH₃CN / methanol / 1.) 0 deg C, 1 h, 2.) room temperature, 16 h

5: 90 percent / Et₃N / 14 h / Ambient temperature

6: 63 percent / 1.) 2.5percent KOH, 2.) 18-crown-6 / 1.) dioxane, room temperature, 14 h, 2.) DMF-H₂O, room temperature, 6 h

7: 75 percent / pyridinium chlorochromate / CH₂Cl₂ / 2 h / Ambient temperature

8: 59 percent / NaBH₃CN / methanol / 1.) 0 deg C, 1 h, 2.) room temperature, 16 h

With potassium hydroxide; 18-crown-6 ether; sodium cyanoborohydride; toluene-4-sulfonic acid; triethylamine; pyridinium chlorochromate; In methanol; dichloromethane;

DOI:10.1021/ja00399a046

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (S)-1-((S)-3-Benzyloxycarbonyl-3-{[(S)-3-benzyloxycarbonyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-tert-butoxycarbonyl-amino}-propyl)-azetidine-2-carboxylic acid benzyl ester (77856-47-4,77881-93-7,83680-33-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / Et₃N / 14 h / Ambient temperature

2: 63 percent / 1.) 2.5percent KOH, 2.) 18-crown-6 / 1.) dioxane, room temperature, 14 h, 2.) DMF-H₂O, room temperature, 6 h

3: 75 percent / pyridinium chlorochromate / CH₂Cl₂ / 2 h / Ambient temperature

4: 59 percent / NaBH₃CN / methanol / 1.) 0 deg C, 1 h, 2.) room temperature, 16 h

With potassium hydroxide; 18-crown-6 ether; sodium cyanoborohydride; triethylamine; pyridinium chlorochromate; In methanol; dichloromethane;

DOI:10.1021/ja00399a046

upstream raw materials:

(S)-Azetidine-2-carboxylic acid benzyl ester; compound with trifluoro-acetic acid

(S)-2-{[(S)-3-Benzyloxycarbonyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-tert-butoxycarbonyl-amino}-4-oxo-butyric acid benzyl ester

3,4-dihydro-2H-pyran

di-tert-butyl dicarbonate

Downstream raw materials:

2'-deoxymugineic acid