(3R,4R)-5-Phenyl-4-(9-phenyl-9H-fluoren-9-ylamino)-pent-1-yn-3-ol

Base Information

• Chemical Name: (3R,4R)-5-Phenyl-4-(9-phenyl-9H-fluoren-9-ylamino)-pent-1-yn-3-ol
• CAS No.: 606124-54-3
• Molecular Formula: C₃₀H₂₅NO
• Molecular Weight: 415.535
• Mol file: 606124-54-3.mol

Synonyms:(3R,4R)-5-Phenyl-4-(9-phenyl-9H-fluoren-9-ylamino)-pent-1-yn-3-ol

Chemical Property of (3R,4R)-5-Phenyl-4-(9-phenyl-9H-fluoren-9-ylamino)-pent-1-yn-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R)-5-Phenyl-4-(9-phenyl-9H-fluoren-9-ylamino)-pent-1-yn-3-ol

There total 1 articles about (3R,4R)-5-Phenyl-4-(9-phenyl-9H-fluoren-9-ylamino)-pent-1-yn-3-ol 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:

3-phenyl-2-(9-phenyl-9H-fluoren-9-ylamino)-propionaldehyde + acetylenemagnesium bromide (4301-14-8) → (3R,4R)-5-Phenyl-4-(9-phenyl-9H-fluoren-9-ylamino)-pent-1-yn-3-ol (606124-54-3) + (3S,4R)-5-Phenyl-4-(9-phenyl-9H-fluoren-9-ylamino)-pent-1-yn-3-ol

Guidance literature:

In tetrahydrofuran; at -40 ℃;

DOI:10.1016/S0040-4039(03)01394-7

Reference yield: 97.0%

benzyl bromide (100-39-0) + (3R,4R)-5-Phenyl-4-(9-phenyl-9H-fluoren-9-ylamino)-pent-1-yn-3-ol (606124-54-3) → ((1R,2R)-1-Benzyl-2-benzyloxy-but-3-ynyl)-(9-phenyl-9H-fluoren-9-yl)-amine (606124-56-5)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 0 ℃;

DOI:10.1016/S0040-4039(03)01394-7

Reference yield:

(3R,4R)-5-Phenyl-4-(9-phenyl-9H-fluoren-9-ylamino)-pent-1-yn-3-ol (606124-54-3) → bestatin (58970-76-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 97 percent / NaH; Bu₄NI / tetrahydrofuran / 0 °C

2.1: 87 percent / KMnO₄; acetic acid; water / pentane

3.1: 91 percent / DCC; HOBT; TsOH / Et₃N / tetrahydrofuran / 0 °C

4.1: LiOH / tetrahydrofuran; H₂O / 0 °C

4.2: H₂ / Pd/C / methanol / 50 °C

With lithium hydroxide; potassium permanganate; water; tetra-(n-butyl)ammonium iodide; sodium hydride; benzotriazol-1-ol; toluene-4-sulfonic acid; acetic acid; dicyclohexyl-carbodiimide; triethylamine; In tetrahydrofuran; water; pentane;

DOI:10.1016/S0040-4039(03)01394-7

upstream raw materials:

acetylenemagnesium bromide

Downstream raw materials:

((1R,2R)-1-Benzyl-2-benzyloxy-but-3-ynyl)-(9-phenyl-9H-fluoren-9-yl)-amine

bestatin

(2S,3R)-2-O-benzyl-4-phenyl-3-[(9-phenyl-9-fluorenyl)-amino]-phenylbutanoic acid

methyl N-{(2S,3R)-2-O-benzyl-4-phenyl-3-[9-phenyl-9-fluorenyl-amino]-butanoyl}-L-leucine