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

Base Information

• Chemical Name: Hexanedioic acid mono-[(3R,5S)-1-(toluene-4-sulfonyl)-5-(toluene-4-sulfonyloxymethyl)-pyrrolidin-3-yl] ester
• CAS No.: 141850-22-8
• Molecular Formula: C₂₅H₃₁NO₉S₂
• Molecular Weight: 553.654
• Mol file: 141850-22-8.mol

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

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

There total 6 articles about Hexanedioic acid mono-[(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: 77.0%

6-Oxo-hexanoic acid (3R,5S)-1-(toluene-4-sulfonyl)-5-(toluene-4-sulfonyloxymethyl)-pyrrolidin-3-yl ester → Hexanedioic acid mono-[(3R,5S)-1-(toluene-4-sulfonyl)-5-(toluene-4-sulfonyloxymethyl)-pyrrolidin-3-yl] ester (141850-22-8)

Guidance literature:

With dipyridinium dichromate; In N,N-dimethyl-formamide; for 6h; Ambient temperature;

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) → Hexanedioic acid mono-[(3R,5S)-1-(toluene-4-sulfonyl)-5-(toluene-4-sulfonyloxymethyl)-pyrrolidin-3-yl] ester (141850-22-8)

Guidance literature:

Multi-step reaction with 4 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

3: 72 percent / O₃, Me₂S / CH₂Cl₂ / 24 h / Ambient temperature

4: 77 percent / PDC / dimethylformamide / 6 h / Ambient temperature

With pyridine; dmap; dipyridinium dichromate; dimethylsulfide; ozone; dicyclohexyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00040a013

Reference yield:

hept-6-enoic acid (1119-60-4) → Hexanedioic acid mono-[(3R,5S)-1-(toluene-4-sulfonyl)-5-(toluene-4-sulfonyloxymethyl)-pyrrolidin-3-yl] ester (141850-22-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 64 percent / DMAP, DCC / CH₂Cl₂ / a) 0 deg C, 5 min, b) r.t., overnight

2: 72 percent / O₃, Me₂S / CH₂Cl₂ / 24 h / Ambient temperature

3: 77 percent / PDC / dimethylformamide / 6 h / Ambient temperature

With dmap; dipyridinium dichromate; dimethylsulfide; ozone; dicyclohexyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00040a013

upstream raw materials:

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

hept-6-enoic acid

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

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

Downstream raw materials:

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

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

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

Refernces