(R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propionic acid (R)-2-((2S,4S,5S,6S)-5-benzyloxycarbonylamino-4-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-phenyl-ethyl ester

Base Information

• Chemical Name: (R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propionic acid (R)-2-((2S,4S,5S,6S)-5-benzyloxycarbonylamino-4-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-phenyl-ethyl ester
• CAS No.: 201158-87-4
• Molecular Formula: C₄₆H₄₆N₂O₉
• Molecular Weight: 770.879
• Mol file: 201158-87-4.mol

Synonyms:(R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propionic acid (R)-2-((2S,4S,5S,6S)-5-benzyloxycarbonylamino-4-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-phenyl-ethyl ester

Chemical Property of (R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propionic acid (R)-2-((2S,4S,5S,6S)-5-benzyloxycarbonylamino-4-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-phenyl-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propionic acid (R)-2-((2S,4S,5S,6S)-5-benzyloxycarbonylamino-4-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-phenyl-ethyl ester

There total 10 articles about (R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propionic acid (R)-2-((2S,4S,5S,6S)-5-benzyloxycarbonylamino-4-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-phenyl-ethyl 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: 88.0%

Fmoc-D-Phe-OH (86123-10-6) + [(2S,3S,4S,6S)-4-Hydroxy-6-((R)-2-hydroxy-1-phenyl-ethoxy)-2-methyl-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester (201158-82-9) → (R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propionic acid (R)-2-((2S,4S,5S,6S)-5-benzyloxycarbonylamino-4-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-phenyl-ethyl ester (201158-87-4)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; for 1.16667h;

DOI:10.1021/jo971380i

Reference yield:

(2R,3S)-2-{[(benzyloxy)carbonyl]amino}-3-hydroxybutanoic acid (5618-95-1,19728-63-3,41151-16-0,85995-53-5,119221-16-8,80384-27-6) → (R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propionic acid (R)-2-((2S,4S,5S,6S)-5-benzyloxycarbonylamino-4-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-phenyl-ethyl ester (201158-87-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 73 percent / p-toluenesulfonic acid / benzene / 3 h / Heating

2: 72 percent / cyanuric chloride, pyridine / CH₂Cl₂ / 50 h

3: 86 percent / tetrahydrofuran; diethyl ether / 2.5 h / -78 °C

4: 64 percent / TFA / methanol / 0.25 h

5: 78 percent / tetramethylammonium triacetoxyborohydride / acetic acid; acetonitrile / 4 h / -28 °C

6: 82 percent / ozone / methanol / 1 h / -78 °C

7: 1.) pyridine, 2.) BF₃-Et₂O / 2.) toluene, 0 deg C, 2 h

8: 78 percent / MeONa / methanol / 5 h

9: 66 percent / QF-3H₂O / tetrahydrofuran

10: 88 percent / triphenylphosphine, DEAD / tetrahydrofuran / 1.17 h

With pyridine; 1,3,5-trichloro-2,4,6-triazine; QF-3H₂O; boron trifluoride diethyl etherate; sodium methylate; toluene-4-sulfonic acid; ozone; triphenylphosphine; trifluoroacetic acid; tetramethylammonium triacetoxyborohydride; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetic acid; acetonitrile; benzene;

DOI:10.1021/jo971380i

Reference yield:

[(1R,2S)-2-Hydroxy-1-((S)-1-hydroxy-ethyl)-pent-4-enyl]-carbamic acid benzyl ester (201158-42-1) → (R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propionic acid (R)-2-((2S,4S,5S,6S)-5-benzyloxycarbonylamino-4-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-phenyl-ethyl ester (201158-87-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 82 percent / ozone / methanol / 1 h / -78 °C

2: 1.) pyridine, 2.) BF₃-Et₂O / 2.) toluene, 0 deg C, 2 h

3: 78 percent / MeONa / methanol / 5 h

4: 66 percent / QF-3H₂O / tetrahydrofuran

5: 88 percent / triphenylphosphine, DEAD / tetrahydrofuran / 1.17 h

With pyridine; QF-3H₂O; boron trifluoride diethyl etherate; sodium methylate; ozone; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol;

DOI:10.1021/jo971380i

upstream raw materials:

Fmoc-D-Phe-OH

[(2S,3S,4S,6S)-4-Hydroxy-6-((R)-2-hydroxy-1-phenyl-ethoxy)-2-methyl-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester

(2R,3S)-2-{[(benzyloxy)carbonyl]amino}-3-hydroxybutanoic acid

[(1R,2S)-2-Hydroxy-1-((S)-1-hydroxy-ethyl)-pent-4-enyl]-carbamic acid benzyl ester