3-(Benzyloxy)-2-hydroxypropanoic acid

Base Information

• Chemical Name: 3-(Benzyloxy)-2-hydroxypropanoic acid
• CAS No.: 127744-27-8
• Molecular Formula: C₁₀H₁₂O₄
• Molecular Weight: 196.203
• DSSTox Substance ID: DTXSID60452122
• Mol file: 127744-27-8.mol

Synonyms:3-(BENZYLOXY)-2-HYDROXYPROPANOIC ACID;374936-90-0;2-hydroxy-3-phenylmethoxypropanoic acid;SCHEMBL1360318;DTXSID60452122;AKOS015967025;3-(BENZYLOXY)-2-HYDROXYPROPANOICACID;W-205286;F1916-0250

Chemical Property of 3-(Benzyloxy)-2-hydroxypropanoic acid

Chemical Property:

• Boiling Point: 387.0±32.0 °C(Predicted)
• PKA: 3.43±0.11(Predicted)
• PSA: 66.76000
• Density: 1.272±0.06 g/cm3(Predicted)
• LogP: 0.64870
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 196.07355886
• Heavy Atom Count: 14
• Complexity: 175

Purity/Quality:

99% ^*data from raw suppliers

(S)-3-(benzyloxy)-2-hydroxypropanoicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COCC(C(=O)O)O

Technology Process of 3-(Benzyloxy)-2-hydroxypropanoic acid

There total 9 articles about 3-(Benzyloxy)-2-hydroxypropanoic 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: 96.0%

O-Benzyl-L-serine (4726-96-9,32520-12-0) → (S)-3-(benzyloxy)-2-hydroxypropanoic acid (130111-08-9,127744-27-8)

Guidance literature:

With sulfuric acid; sodium nitrite; In water; at 0 - 20 ℃; for 22.83h;

DOI:10.1002/anie.202002328

Reference yield: 92.0%

O-benzyl-D-serine (10433-52-0,32520-12-0) → 3-(benzyloxy)-(R)-2-hydroxy-propionic acid (127744-27-8,130111-08-9)

Guidance literature:

With sulfuric acid; water; sodium nitrite; at 0 - 20 ℃; for 27h;

DOI:10.1039/c2cc31669b

Reference yield:

H-Ser(OBn)-OH trifluoroacetate (68761-98-8) → (S)-3-(benzyloxy)-2-hydroxypropanoic acid (130111-08-9,127744-27-8)

Guidance literature:

With tert.-butylnitrite; water; In 1,4-dioxane; at 20 ℃; for 1h; Inert atmosphere; Cooling with ice;

DOI:10.1016/j.tetlet.2014.05.090

upstream raw materials:

methyl 6-O-benzyl-α-D-galactopyranoside

benzyl chloride

O-benzyl-D-serine

O-Benzyl-L-serine

Downstream raw materials:

methyl (2R)-3-benzyloxy-2-hydroxypropanoate

(S)-methyl 3-(benzyloxy)-2-hydroxypropanoate

(R)-3-(2-(benzyloxy)-1-(6-chlorothiazolo[5,4-b]pyridin-2-yl)ethoxy)-2,6-difluorobenzonitrile

(R)-3-(benzyloxy)-2-(3-carbamoyl-2,4-difluorophenoxy)propanoyl chloride

Refernces

• 1、 Bach, Thorsten,Grab, Hanusch A.,Kirsch, Volker C.,Sieber, Stephan A.. "Total Synthesis of the Cyclic Depsipeptide Vioprolide D via its (Z)-Diastereoisomer". . p. 12357 - 12361. Retrieved 2020.
• 2、 Bartling, Christian R. O.,Jensen, Thomas M. T.,Henry, Shawna M.,Colliander, Anna L.,Sereikaite, Vita,Wenzler, Marcella,Jain, Palash,Maric, Hans M.,Harps?e, Kasper,Pedersen, S?ren W.,Clemmensen, Louise S.,Haugaard-Kedstr?m, Linda M.,Gloriam, David E.,Ho, Angela,Str?mgaard, Kristian. "Targeting the APP-Mint2 Protein-Protein Interaction with a Peptide-Based Inhibitor Reduces Amyloid-β Formation". . p. 891 - 901. Retrieved 2021.
• 3、 -. "PROTEIN TYROSINE PHOSPHATASE DEGRADERS AND METHODS OF USE THEREOF". Page/Page column 493. . Retrieved 2021/06/26.