(S)-methyl 2-((3R,4S)-4-hydroxy-1,5-diphenylpent-1-yn-3-ylamino)-3-phenylpropanoate

Base Information

• Chemical Name: (S)-methyl 2-((3R,4S)-4-hydroxy-1,5-diphenylpent-1-yn-3-ylamino)-3-phenylpropanoate
• CAS No.: 1334430-58-8
• Molecular Formula: C₂₇H₂₇NO₃
• Molecular Weight: 413.516
• Mol file: 1334430-58-8.mol

Synonyms:(S)-methyl 2-((3R,4S)-4-hydroxy-1,5-diphenylpent-1-yn-3-ylamino)-3-phenylpropanoate

Chemical Property of (S)-methyl 2-((3R,4S)-4-hydroxy-1,5-diphenylpent-1-yn-3-ylamino)-3-phenylpropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-methyl 2-((3R,4S)-4-hydroxy-1,5-diphenylpent-1-yn-3-ylamino)-3-phenylpropanoate

There total 3 articles about (S)-methyl 2-((3R,4S)-4-hydroxy-1,5-diphenylpent-1-yn-3-ylamino)-3-phenylpropanoate 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: 86.0%

diethyl (phenylethynyl)boronate (1334430-38-4) + methyl (2S)-2-amino-3-phenylpropanoate (2577-90-4) + (5S,4RS)-5-benzyl-2,2-dimethyl-4-hydroxy-1,3-dioxolane → (S)-methyl 2-((3R,4S)-4-hydroxy-1,5-diphenylpent-1-yn-3-ylamino)-3-phenylpropanoate (1334430-58-8)

Guidance literature:

methyl (2S)-2-amino-3-phenylpropanoate; (5S,4RS)-5-benzyl-2,2-dimethyl-4-hydroxy-1,3-dioxolane; With (R)-3,3'-dibromo-1,1'-bi-2-naphthol; In α,α,α-trifluorotoluene; for 0.0333333h; Inert atmosphere;

diethyl (phenylethynyl)boronate; In α,α,α-trifluorotoluene; at 20 ℃; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1002/anie.201103271

Reference yield: 62.0%

diethyl (phenylethynyl)boronate (1334430-38-4) + methyl (2S)-2-amino-3-phenylpropanoate (2577-90-4) + (5S,4RS)-5-benzyl-2,2-dimethyl-4-hydroxy-1,3-dioxolane → (S)-methyl 2-((3R,4S)-4-hydroxy-1,5-diphenylpent-1-yn-3-ylamino)-3-phenylpropanoate (1334430-58-8) + (S)-methyl 2-((3S,4S)-4-hydroxy-1,5-diphenylpent-1-yn-3-ylamino)-3-phenylpropanoate (1334430-59-9)

Guidance literature:

methyl (2S)-2-amino-3-phenylpropanoate; (5S,4RS)-5-benzyl-2,2-dimethyl-4-hydroxy-1,3-dioxolane; With (S)-3,3'-dibromo-1,1'-bi-2-naphthol; In α,α,α-trifluorotoluene; for 0.0333333h; Inert atmosphere; Molecular sieve;

diethyl (phenylethynyl)boronate; In α,α,α-trifluorotoluene; at 20 ℃; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1002/anie.201103271

Reference yield:

2-phenyl-1-ethynylboronic acid (918487-96-4) → (S)-methyl 2-((3R,4S)-4-hydroxy-1,5-diphenylpent-1-yn-3-ylamino)-3-phenylpropanoate (1334430-58-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: magnesium sulfate / chloroform / 24 h / Inert atmosphere; Reflux

2.1: (R)-3,3'-dibromo-1,1'-bi-2-naphthol / α,α,α-trifluorotoluene / 0.03 h / Inert atmosphere

2.2: 20 °C / Inert atmosphere

With magnesium sulfate; (R)-3,3'-dibromo-1,1'-bi-2-naphthol; In chloroform; α,α,α-trifluorotoluene; 2.2: Petasis reaction;

DOI:10.1002/anie.201103271

upstream raw materials:

2-phenyl-1-ethynylboronic acid

diethyl (phenylethynyl)boronate

methyl (2S)-2-amino-3-phenylpropanoate