Hept-6-enoic acid (3R,5S)-1-(toluene-4-sulfonyl)-5-(toluene-4-sulfonyloxymethyl)-pyrrolidin-3-yl ester

Base Information

• Chemical Name: Hept-6-enoic acid (3R,5S)-1-(toluene-4-sulfonyl)-5-(toluene-4-sulfonyloxymethyl)-pyrrolidin-3-yl ester
• CAS No.: 141850-21-7
• Molecular Formula: C₂₆H₃₃NO₇S₂
• Molecular Weight: 535.683
• Mol file: 141850-21-7.mol

Synonyms:Hept-6-enoic acid (3R,5S)-1-(toluene-4-sulfonyl)-5-(toluene-4-sulfonyloxymethyl)-pyrrolidin-3-yl ester

Chemical Property of Hept-6-enoic acid (3R,5S)-1-(toluene-4-sulfonyl)-5-(toluene-4-sulfonyloxymethyl)-pyrrolidin-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Hept-6-enoic acid (3R,5S)-1-(toluene-4-sulfonyl)-5-(toluene-4-sulfonyloxymethyl)-pyrrolidin-3-yl ester

There total 3 articles about Hept-6-enoic acid (3R,5S)-1-(toluene-4-sulfonyl)-5-(toluene-4-sulfonyloxymethyl)-pyrrolidin-3-yl 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: 64.0%

hept-6-enoic acid (1119-60-4) + (2S,4R)-(1-tosyl-4-(tosyloxy)pyrrolidin-2-yl)methyl 4-methylbenzenesulfonate (141850-60-4) → Hept-6-enoic acid (3R,5S)-1-(toluene-4-sulfonyl)-5-(toluene-4-sulfonyloxymethyl)-pyrrolidin-3-yl ester (141850-21-7)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; a) 0 deg C, 5 min, b) r.t., overnight;

DOI:10.1021/jo00040a013

Reference yield:

(2S,4R)-2-Hydroxymethyl-4-hydroxy-1-(4-toluenesulfonyl)-pyrrolidine (57850-05-2,93136-91-5,116143-08-9,132998-42-6,5605-46-9) → Hept-6-enoic acid (3R,5S)-1-(toluene-4-sulfonyl)-5-(toluene-4-sulfonyloxymethyl)-pyrrolidin-3-yl ester (141850-21-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / pyridine / 2 h / -20 °C

2: 64 percent / DMAP, DCC / CH₂Cl₂ / a) 0 deg C, 5 min, b) r.t., overnight

With pyridine; dmap; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1021/jo00040a013

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → Hept-6-enoic acid (3R,5S)-1-(toluene-4-sulfonyl)-5-(toluene-4-sulfonyloxymethyl)-pyrrolidin-3-yl ester (141850-21-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / pyridine / 2 h / -20 °C

2: 64 percent / DMAP, DCC / CH₂Cl₂ / a) 0 deg C, 5 min, b) r.t., overnight

With pyridine; dmap; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1021/jo00040a013

upstream raw materials:

hept-6-enoic acid

(2S,4R)-(1-tosyl-4-(tosyloxy)pyrrolidin-2-yl)methyl 4-methylbenzenesulfonate

(2S,4R)-2-Hydroxymethyl-4-hydroxy-1-(4-toluenesulfonyl)-pyrrolidine

p-toluenesulfonyl chloride

Downstream raw materials:

Hexanedioic acid mono-[(3R,5S)-1-(toluene-4-sulfonyl)-5-(toluene-4-sulfonyloxymethyl)-pyrrolidin-3-yl] ester

Hexanedioic acid mono-[(3R,5S)-5-iodomethyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl] ester

(1R,11S)-12-(Toluene-4-sulfonyl)-2,9-dioxa-12-aza-bicyclo[9.2.1]tetradecane-3,8-dione

(R)-5-Methylene-1-(toluene-4-sulfonyl)-pyrrolidin-3-ol

Refernces