(3S,4S)-4-(N-allyl-4-methylphenylsulfonamido)-1,3-diphenylhept-1-yn-3-yl cyclopropanecarboxylate

Base Information

• Chemical Name: (3S,4S)-4-(N-allyl-4-methylphenylsulfonamido)-1,3-diphenylhept-1-yn-3-yl cyclopropanecarboxylate
• CAS No.: 1427519-95-6
• Molecular Formula: C₃₃H₃₅NO₄S
• Molecular Weight: 541.711
• Mol file: 1427519-95-6.mol

Synonyms:(3S,4S)-4-(N-allyl-4-methylphenylsulfonamido)-1,3-diphenylhept-1-yn-3-yl cyclopropanecarboxylate

Chemical Property of (3S,4S)-4-(N-allyl-4-methylphenylsulfonamido)-1,3-diphenylhept-1-yn-3-yl cyclopropanecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3S,4S)-4-(N-allyl-4-methylphenylsulfonamido)-1,3-diphenylhept-1-yn-3-yl cyclopropanecarboxylate

There total 2 articles about (3S,4S)-4-(N-allyl-4-methylphenylsulfonamido)-1,3-diphenylhept-1-yn-3-yl cyclopropanecarboxylate 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:

C30H31NO4S + allyl bromide (106-95-6) → (3S,4S)-4-(N-allyl-4-methylphenylsulfonamido)-1,3-diphenylhept-1-yn-3-yl cyclopropanecarboxylate (1427519-95-6)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/jo400121j

Reference yield:

N-((3S,4S)-3-hydroxy-1,3-diphenylhept-1-yn-4-yl)-4-methylbenzenesulfonamide (1383950-50-2) → (3S,4S)-4-(N-allyl-4-methylphenylsulfonamido)-1,3-diphenylhept-1-yn-3-yl cyclopropanecarboxylate (1427519-95-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere

1.2: 0.5 h / 0 °C / Inert atmosphere

2.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

With sodium hydride; lithium hexamethyldisilazane; In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/jo400121j

Reference yield: 97.0%

(3S,4S)-4-(N-allyl-4-methylphenylsulfonamido)-1,3-diphenylhept-1-yn-3-yl cyclopropanecarboxylate (1427519-95-6) → ((3R,6S)-3-methyl-5-phenyl-6-propyl-1-tosyl-1,2,3,6-tetrahydropyridin-4-yl)(phenyl)methanone (1427520-28-2) + cyclopropanecarboxylic acid (1759-53-1)

Guidance literature:

With Echavarren's catalyst; water; In 1,2-dichloro-ethane; at 80 ℃; for 24h; stereoselective reaction; Inert atmosphere;

DOI:10.1021/jo400121j

upstream raw materials:

allyl bromide

N-((3S,4S)-3-hydroxy-1,3-diphenylhept-1-yn-4-yl)-4-methylbenzenesulfonamide

Downstream raw materials:

((3R,6S)-3-methyl-5-phenyl-6-propyl-1-tosyl-1,2,3,6-tetrahydropyridin-4-yl)(phenyl)methanone

cyclopropanecarboxylic acid

2-((3R,6S)-4-benzoyl-5-phenyl-6-propyl-1-tosyl-1,2,3,6-tetrahydropyridin-3-yl)-1-cyclopropylethanone