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

Base Information

• Chemical Name: (2R,3R)-(+)-menthyl 2-amino-3-((4-methoxybenzyl)thio)-3-phenylpropionate
• CAS No.: 114529-89-4
• Molecular Formula: C₂₇H₃₇NO₃S
• Molecular Weight: 455.662
• Mol file: 114529-89-4.mol

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

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

There total 3 articles about (2R,3R)-(+)-menthyl 2-amino-3-((4-methoxybenzyl)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:

(1S,2R,5S)-2-isopropyl-5-methylcyclohexyl cinnamate (160865-72-5) → (2R,3R)-(+)-menthyl 2-amino-3-((4-methoxybenzyl)thio)-3-phenylpropionate (114529-89-4)

Guidance literature:

Multi-step reaction with 3 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

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

DOI:10.1021/jo00249a006

Reference yield:

erythro-(+)-mentyl 2,3-dibromo-3-phenylpropionate → (2R,3R)-(+)-menthyl 2-amino-3-((4-methoxybenzyl)thio)-3-phenylpropionate (114529-89-4)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With boron trifluoride diethyl etherate; ammonia; In methanol; dichloromethane;

DOI:10.1021/jo00249a006

Reference yield:

p-methoxybenzylmercaptan (6258-60-2) + cis-(2S,3S)-2-((+)-menthyloxycarbonyl)-3-phenylaziridine (114529-88-3) → (2R,3R)-(+)-menthyl 2-amino-3-((4-methoxybenzyl)thio)-3-phenylpropionate (114529-89-4)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; for 15h; Ambient temperature;

DOI:10.1021/jo00249a006

upstream raw materials:

p-methoxybenzylmercaptan

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

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

Downstream raw materials:

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

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