(R)-alpha-(Acetylamino)-p-acetoxybenzenepropanoic acid

Base Information

• Chemical Name: (R)-alpha-(Acetylamino)-p-acetoxybenzenepropanoic acid
• CAS No.: 61478-30-6
• Molecular Formula: C13H15NO5
• Molecular Weight: 265.266
• DSSTox Substance ID: DTXSID201283415
• Nikkaji Number: J304.838A
• Mol file: 61478-30-6.mol

Synonyms:SCHEMBL11183676;DTXSID201283415;AKOS015889974;D-Tyrosine, N-acetyl-, acetate (ester);(R)-alpha-(Acetylamino)-p-acetoxybenzenepropanoic acid;61478-30-6

Chemical Property of (R)-alpha-(Acetylamino)-p-acetoxybenzenepropanoic acid

Chemical Property:

• XLogP3: -0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 265.09502258
• Heavy Atom Count: 19
• Complexity: 347

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)NC(CC1=CC=C(C=C1)OC(=O)C)C(=O)O
• Isomeric SMILES: CC(=O)N[C@H](CC1=CC=C(C=C1)OC(=O)C)C(=O)O

Technology Process of (R)-alpha-(Acetylamino)-p-acetoxybenzenepropanoic acid

There total 4 articles about (R)-alpha-(Acetylamino)-p-acetoxybenzenepropanoic acid 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:

(Z)-α-Acetamido-p-acetyloxycinnamic Acid (64896-34-0) → N-acetyl-O-acetyl-L-tyrosine (17355-23-6) + O,N-diacetyltyrosine (61478-30-6)

Guidance literature:

With hydrogen; triethylamine; Rh(I)-phosphine 22; In ethanol; at 20 ℃; under 41371.8 Torr; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo00327a023

Reference yield:

4-acetoxy-α-acetylamino-cinnamic acid (52507-18-3) → N-acetyl-O-acetyl-L-tyrosine (17355-23-6) + O,N-diacetyltyrosine (61478-30-6)

Guidance literature:

With hydrogen; ClO4; (2R,3S)-1,2-bis(diphenylphosphino)-3-tBoc-aminobutane; In ethanol; for 22h; Yield given; Ambient temperature;

Reference yield:

(Z)-α-Acetamido-p-acetyloxycinnamic Acid (64896-34-0) → O,N-diacetyltyrosine (61478-30-6)

Guidance literature:

With (1,5-cyclooctadiene)<(S,S)-1,3-propanediyl<<(omethoxyphenyl)phenylphosphine>>rhodium tetrafluoroborate; hydrogen; In ethanol; at 45 ℃; for 24h; under 11400 Torr;

DOI:10.1021/jo00387a010

upstream raw materials:

tyrosine

acetic anhydride

4-acetoxy-α-acetylamino-cinnamic acid

(Z)-α-Acetamido-p-acetyloxycinnamic Acid

Refernces

• 1、 Takahashi, Hisashi,Achiwa, Kazuo. "Efficient Asymmetric Hydrogenations of (Z)-2-Acetamidoacrylic Acid Derivatives with the Cationic Rhodium Complex of (2S,4S)-MOD-BPPM". . p. 305 - 308. Retrieved 2007/10/02.
• 2、 Saito, Kunio,Saijo, Shigeyoshi,Kotera, Keishi,Date, Tadamasa. "Asymmetric Hydrogenation Catalyzed by Rhodium Complex with a New Chiral Bisphosphine Derived from L-Threonine". . p. 1342 - 1350. Retrieved 2007/10/02.