(2R,3R)-(+)-menthyl 2-amino-3-((S-3-nitro-2-pyridinesulfenyl)thio)-3-phenylpropionate

Base Information

• Chemical Name: (2R,3R)-(+)-menthyl 2-amino-3-((S-3-nitro-2-pyridinesulfenyl)thio)-3-phenylpropionate
• CAS No.: 114466-84-1
• Molecular Formula: C₂₄H₃₁N₃O₄S₂
• Molecular Weight: 489.66
• Mol file: 114466-84-1.mol

Synonyms:(2R,3R)-(+)-menthyl 2-amino-3-((S-3-nitro-2-pyridinesulfenyl)thio)-3-phenylpropionate

Chemical Property of (2R,3R)-(+)-menthyl 2-amino-3-((S-3-nitro-2-pyridinesulfenyl)thio)-3-phenylpropionate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-(+)-menthyl 2-amino-3-((S-3-nitro-2-pyridinesulfenyl)thio)-3-phenylpropionate

There total 4 articles about (2R,3R)-(+)-menthyl 2-amino-3-((S-3-nitro-2-pyridinesulfenyl)thio)-3-phenylpropionate 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: 95.0%

3-nitro-2-pyridinesulfenyl chloride (68206-45-1) + (2R,3R)-(+)-menthyl 2-amino-3-((4-methoxybenzyl)thio)-3-phenylpropionate (114529-89-4) → (2R,3R)-(+)-menthyl 2-amino-3-((S-3-nitro-2-pyridinesulfenyl)thio)-3-phenylpropionate (114466-84-1)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 0.25h;

DOI:10.1021/jo00249a006

Reference yield:

(1S,2R,5S)-2-isopropyl-5-methylcyclohexyl cinnamate (160865-72-5) → (2R,3R)-(+)-menthyl 2-amino-3-((S-3-nitro-2-pyridinesulfenyl)thio)-3-phenylpropionate (114466-84-1)

Guidance literature:

Multi-step reaction with 4 steps

1: Br₂ / CHCl₃ / 3 h / Ambient temperature

2: NH₃(liquid) / methanol; CH₂Cl₂ / 120 h / Ambient temperature

3: BF₃*Et₂O / CH₂Cl₂ / 15 h / Ambient temperature

4: 95 percent / CF₃COOH / CH₂Cl₂ / 0.25 h / 0 °C

With boron trifluoride diethyl etherate; ammonia; bromine; trifluoroacetic acid; In methanol; dichloromethane; chloroform;

DOI:10.1021/jo00249a006

Reference yield:

cis-(2S,3S)-2-((+)-menthyloxycarbonyl)-3-phenylaziridine (114529-88-3) → (2R,3R)-(+)-menthyl 2-amino-3-((S-3-nitro-2-pyridinesulfenyl)thio)-3-phenylpropionate (114466-84-1)

Guidance literature:

Multi-step reaction with 2 steps

1: BF₃*Et₂O / CH₂Cl₂ / 15 h / Ambient temperature

2: 95 percent / CF₃COOH / CH₂Cl₂ / 0.25 h / 0 °C

With boron trifluoride diethyl etherate; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/jo00249a006

upstream raw materials:

3-nitro-2-pyridinesulfenyl chloride

(2R,3R)-(+)-menthyl 2-amino-3-((4-methoxybenzyl)thio)-3-phenylpropionate

(1S,2R,5S)-2-isopropyl-5-methylcyclohexyl cinnamate

cis-(2S,3S)-2-((+)-menthyloxycarbonyl)-3-phenylaziridine

Downstream raw materials:

(2R,3R)-2-((tert-butyloxycarbonyl)amino)-3-((S-3-nitro-2-pyridinesulfenyl)thio)-3-phenylpropionic acid