D-Proline, 1-acetyl-4-[[(4-methylphenyl)sulfonyl]oxy]-, methyl ester, cis-

Base Information

• Chemical Name: D-Proline, 1-acetyl-4-[[(4-methylphenyl)sulfonyl]oxy]-, methyl ester, cis-
• CAS No.: 77449-95-7
• Molecular Formula: C15H19NO6S
• Molecular Weight: 341.385
• DSSTox Substance ID: DTXSID901145783
• Mol file: 77449-95-7.mol

Synonyms:DTXSID901145783;D-Proline, 1-acetyl-4-[[(4-methylphenyl)sulfonyl]oxy]-, methyl ester, cis-;77449-95-7

Chemical Property of D-Proline, 1-acetyl-4-[[(4-methylphenyl)sulfonyl]oxy]-, methyl ester, cis-

Chemical Property:

• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 341.09330850
• Heavy Atom Count: 23
• Complexity: 547

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OC2CC(N(C2)C(=O)C)C(=O)OC
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)O[C@@H]2C[C@@H](N(C2)C(=O)C)C(=O)OC

Technology Process of D-Proline, 1-acetyl-4-[[(4-methylphenyl)sulfonyl]oxy]-, methyl ester, cis-

There total 12 articles about D-Proline, 1-acetyl-4-[[(4-methylphenyl)sulfonyl]oxy]-, methyl ester, cis- 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:

(2-propenyl)propanedioic acid diethyl ester (2049-80-1) → cis-1-acetyl-4-(toluene-4-sulfonyloxy)-DL-proline-methyl ester (57750-51-3,77449-95-7,78804-97-4)

Guidance literature:

Multi-step reaction with 5 steps

1: acetic acid; concentrated aqueous hydrochloric acid; sulfuryl chloride

2: aqueous NH₃ / 100 °C

3: acetic acid

4: diethyl ether; dioxane

5: pyridine

With 1,4-dioxane; pyridine; hydrogenchloride; ammonium hydroxide; sulfuryl dichloride; diethyl ether; acetic acid;

DOI:10.1021/ja01630a038

Reference yield:

3-bromo-5-chloromethyl-dihydro-furan-2-one (854657-58-2) → cis-1-acetyl-4-(toluene-4-sulfonyloxy)-DL-proline-methyl ester (57750-51-3,77449-95-7,78804-97-4)

Guidance literature:

Multi-step reaction with 4 steps

1: aqueous NH₃ / 100 °C

2: acetic acid

3: diethyl ether; dioxane

4: pyridine

With 1,4-dioxane; pyridine; ammonium hydroxide; diethyl ether; acetic acid;

DOI:10.1021/ja01630a038

Reference yield:

3-chloro-5-chloromethyl-dihydro-furan-2-one (2584-72-7) → cis-1-acetyl-4-(toluene-4-sulfonyloxy)-DL-proline-methyl ester (57750-51-3,77449-95-7,78804-97-4)

Guidance literature:

Multi-step reaction with 4 steps

1: aqueous NH₃ / 100 °C

2: acetic acid

3: diethyl ether; dioxane

4: pyridine

With 1,4-dioxane; pyridine; ammonium hydroxide; diethyl ether; acetic acid;

DOI:10.1021/ja01630a038

upstream raw materials:

diazomethane

N-Acetyl-allo-4-hydroxy-D-proline

p-toluenesulfonyl chloride

cis-1-acetyl-4-hydroxy-DL-proline-methyl ester

Downstream raw materials:

trans-4-hydroxyproline

trans-4-hydroxy-D,L-proline

cis-1-acetyl-4-(toluene-4-sulfonyloxy)-DL-proline

N-Acetyl-allo-4-(p-toluenesulfonyloxy)-D-proline