(S)-4-[tert-Butoxycarbonyl-((S)-2-oxo-tetrahydro-furan-3-yl)-amino]-2-(tetrahydro-pyran-2-yloxy)-butyric acid benzyl ester

Base Information

• Chemical Name: (S)-4-[tert-Butoxycarbonyl-((S)-2-oxo-tetrahydro-furan-3-yl)-amino]-2-(tetrahydro-pyran-2-yloxy)-butyric acid benzyl ester
• CAS No.: 77856-42-9
• Molecular Formula: C₂₅H₃₅NO₈
• Molecular Weight: 477.555
• Mol file: 77856-42-9.mol

Synonyms:

Chemical Property of (S)-4-[tert-Butoxycarbonyl-((S)-2-oxo-tetrahydro-furan-3-yl)-amino]-2-(tetrahydro-pyran-2-yloxy)-butyric acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-4-[tert-Butoxycarbonyl-((S)-2-oxo-tetrahydro-furan-3-yl)-amino]-2-(tetrahydro-pyran-2-yloxy)-butyric acid benzyl ester

There total 10 articles about (S)-4-[tert-Butoxycarbonyl-((S)-2-oxo-tetrahydro-furan-3-yl)-amino]-2-(tetrahydro-pyran-2-yloxy)-butyric 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: 90.0%

di-tert-butyl dicarbonate (24424-99-5) + (S)-4-((S)-2-Oxo-tetrahydro-furan-3-ylamino)-2-(tetrahydro-pyran-2-yloxy)-butyric acid benzyl ester (77856-41-8,77881-89-1,83680-32-4,120964-20-7) → (S)-4-[tert-Butoxycarbonyl-((S)-2-oxo-tetrahydro-furan-3-yl)-amino]-2-(tetrahydro-pyran-2-yloxy)-butyric acid benzyl ester (77856-42-9,77881-90-4,83680-36-8)

Guidance literature:

With triethylamine; for 14h; Ambient temperature;

DOI:10.1021/ja00399a046

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) → 4-[tert-Butoxycarbonyl-(2-oxo-tetrahydro-furan-3-yl)-amino]-2-(tetrahydro-pyran-2-yloxy)-butyric acid benzyl ester (77856-42-9,77881-90-4,83680-36-8)

Guidance literature:

Multi-step reaction with 5 steps

1: p-TsOH / CH₂Cl₂ / 0.5 h / 0 °C

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

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

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

5: Et₃N / 14 h / Ambient temperature

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:

3,4-dihydro-2H-pyran (110-87-2) → (S)-4-[tert-Butoxycarbonyl-((S)-2-oxo-tetrahydro-furan-3-yl)-amino]-2-(tetrahydro-pyran-2-yloxy)-butyric acid benzyl ester (77856-42-9,77881-90-4,83680-36-8)

Guidance literature:

Multi-step reaction with 5 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

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

DOI:10.1021/ja00399a046

upstream raw materials:

di-tert-butyl dicarbonate

4-(2-Oxo-tetrahydro-furan-3-ylamino)-2-(tetrahydro-pyran-2-yloxy)-butyric acid benzyl ester

3,4-dihydro-2H-pyran

3-(Tetrahydro-pyran-2-yloxy)-dihydro-furan-2-one

Downstream raw materials:

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

(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

2'-deoxymugineic acid

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