(S)-3-(Benzyloxycarbonyl)-3-hydroxypropanoic acid

Base Information

• Chemical Name: (S)-3-(Benzyloxycarbonyl)-3-hydroxypropanoic acid
• CAS No.: 66178-04-9
• Molecular Formula: C₁₁H₁₂O₅
• Molecular Weight: 224.213
• DSSTox Substance ID: DTXSID101260092
• Nikkaji Number: J1.285.777B
• Mol file: 66178-04-9.mol

Synonyms:(S)-3-(Benzyloxycarbonyl)-3-hydroxypropanoic acid

Chemical Property of (S)-3-(Benzyloxycarbonyl)-3-hydroxypropanoic acid

Chemical Property:

• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 224.06847348
• Heavy Atom Count: 16
• Complexity: 245

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)C(CC(=O)O)O
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)[C@H](CC(=O)O)O

Technology Process of (S)-3-(Benzyloxycarbonyl)-3-hydroxypropanoic acid

There total 2 articles about (S)-3-(Benzyloxycarbonyl)-3-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: 91.0%

(S)-Malic acid (97-67-6,78644-42-5) + benzyl alcohol (100-51-6,185532-71-2) → (S)-3-(Benzyloxycarbonyl)-3-hydroxypropanoic acid (66178-04-9)

Guidance literature:

(S)-Malic acid; With (CF₃CO₂)2O; at 20 ℃; for 0.666667h;

benzyl alcohol; at 20 ℃; for 3h;

DOI:10.1055/s-2005-870018

Reference yield:

(3S)-2,5-dioxotetrahydrofuran-3-yl trifluoroacetate (99529-36-9) + benzyl alcohol (100-51-6,185532-71-2) → (S)-3-(Benzyloxycarbonyl)-3-hydroxypropanoic acid (66178-04-9) + (S)-4-(benzyloxy)-2-hydroxy-4-oxobutanoic acid

Guidance literature:

In dichloromethane; at -25 - 0 ℃; for 18h; Title compound not separated from byproducts.;

DOI:10.1002/1099-0690(200004)2000:7<1207::AID-EJOC1207>3.0.CO;2-2

Reference yield: 92.0%

(S)-3-(Benzyloxycarbonyl)-3-hydroxypropanoic acid (66178-04-9) + allyl bromide (106-95-6) → 4-allyl 1-benzyl (2S)-2-hydroxybutanedioate (276870-98-5)

Guidance literature:

With tetrabutylammomium bromide; potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 4h;

DOI:10.1002/1099-0690(200004)2000:7<1207::AID-EJOC1207>3.0.CO;2-2

upstream raw materials:

(S)-Malic acid

benzyl alcohol

(3S)-2,5-dioxotetrahydrofuran-3-yl trifluoroacetate

Downstream raw materials:

1-benzyl-2(S)-malyl-5(S)-amino-4(S)-<(tert-butyldimethylsilyl)oxy>-2(S)-isopropyl-7-(methyloctanoyl)-2(S)-methylbutylamine

(S)-2-oxazolidinone-5-carboxylic acid benzyl ester

(2S)-hydroxysuccinic acid-1-benzyl ester-4-(4-methoxybenzyl) ester

4-allyl 1-benzyl (2S)-2-hydroxybutanedioate