(1S,2S,4R,6S)-2-Benzoylamino-6-methylsulfanyl-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (1S,2S,4R,6S)-2-Benzoylamino-6-methylsulfanyl-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester
• CAS No.: 127572-43-4
• Molecular Formula: C₁₇H₂₁NO₃S
• Molecular Weight: 319.425
• Mol file: 127572-43-4.mol

Synonyms:(1S,2S,4R,6S)-2-Benzoylamino-6-methylsulfanyl-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester

Chemical Property of (1S,2S,4R,6S)-2-Benzoylamino-6-methylsulfanyl-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,4R,6S)-2-Benzoylamino-6-methylsulfanyl-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester

There total 2 articles about (1S,2S,4R,6S)-2-Benzoylamino-6-methylsulfanyl-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester 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: 75.0%

methyl 2-exo-amino-6-endo-(methylthio)bicyclo<2.2.1>heptane-2-endo-carboxylate (127572-42-3) + benzoyl chloride (98-88-4) → (1S,2S,4R,6S)-2-Benzoylamino-6-methylsulfanyl-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester (127572-43-4)

Guidance literature:

With sodium hydrogencarbonate; In acetonitrile; Ambient temperature;

DOI:10.1021/jo00299a020

Reference yield:

Methyl 6-endo-(Methylthio)bicyclo<2.2.1>heptane-2-endo-carboxylate (64887-94-1) → (1S,2S,4R,6S)-2-Benzoylamino-6-methylsulfanyl-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester (127572-43-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) LDA, 2) O-(mesitylenesulfonyl)hydroxylamine / 1) THF, HMPT, -78 deg C, 3h, 2) THF a) -78 deg C, 2h, b) RT, overnight

2: 75 percent / aq. NaHCO₃ / acetonitrile / Ambient temperature

With mesitylenesulfonylhydroxylamine; sodium hydrogencarbonate; lithium diisopropyl amide; In acetonitrile;

DOI:10.1021/jo00299a020

Reference yield:

(1S,2S,4R,6S)-2-Benzoylamino-6-methylsulfanyl-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester (127572-43-4) → (1R,2R,4S,6R)-2-Benzoylamino-6-((R)-methanesulfinyl)-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester (127572-45-6,127641-40-1)

Guidance literature:

With sodium periodate; In methanol; water; Ambient temperature;

DOI:10.1021/jo00299a020

upstream raw materials:

methyl 2-exo-amino-6-endo-(methylthio)bicyclo<2.2.1>heptane-2-endo-carboxylate

benzoyl chloride

Methyl 6-endo-(Methylthio)bicyclo<2.2.1>heptane-2-endo-carboxylate

Downstream raw materials:

(1R,2R,4S,6R)-2-Benzoylamino-6-((S)-methanesulfinyl)-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester

(1R,2R,4S,6R)-2-Benzoylamino-6-((R)-methanesulfinyl)-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester