(3R,4R)-3,4-Dihydroxy-3-methyloxolan-2-one

Base Information

• Chemical Name: (3R,4R)-3,4-Dihydroxy-3-methyloxolan-2-one
• CAS No.: 18465-71-9
• Molecular Formula: C5H8O4
• Molecular Weight: 132.11500
• UNII: UHG7K52SWD
• DSSTox Substance ID: DTXSID30456056
• Nikkaji Number: J672.759J
• Wikidata: Q72464843
• Mol file: 18465-71-9.mol

Synonyms:18465-71-9;2-C-Methyl-D-erythrono-1,4-lactone;(3R,4R)-3,4-Dihydroxy-3-methyloxolan-2-one;(3R,4R)-3,4-Dihydroxy-3-methyldihydrofuran-2(3H)-one;UHG7K52SWD;2(3H)-Furanone, dihydro-3,4-dihydroxy-3-methyl-, (3R,4R)-;3,4-Dihydroxy-3-methyloxolan-2-one, (3R,4R)-;(3R,4R)-Dihydro-3,4-dihydroxy-3-methyl-2(3H)-furanone;UNII-UHG7K52SWD;2(3H)-Furanone, dihydro-3,4-dihydroxy-3-methyl-, (3R-cis)-;SCHEMBL4653435;DTXSID30456056;2,3-Dihydroxy-2-methylbutyrolactone;AKOS015999005;FS-9430;Erythronic acid,2-C-methyl-,-lactone,D-

Chemical Property of (3R,4R)-3,4-Dihydroxy-3-methyloxolan-2-one

Chemical Property:

• Melting Point: 113 °C
• Boiling Point: 254.0±7.0 °C(Predicted)
• PKA: 12.36±0.40(Predicted)
• PSA: 66.76000
• Density: 1.490±0.06 g/cm3(Predicted)
• LogP: -1.34490
• Storage Temp.: 2-8°C
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 132.04225873
• Heavy Atom Count: 9
• Complexity: 144

Purity/Quality:

97% ^*data from raw suppliers

2-C-Methyl-D-erythrono-1,4-lactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(COC1=O)O)O
• Isomeric SMILES: C[C@]1([C@@H](COC1=O)O)O

Technology Process of (3R,4R)-3,4-Dihydroxy-3-methyloxolan-2-one

There total 24 articles about (3R,4R)-3,4-Dihydroxy-3-methyloxolan-2-one 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: 95.0%

(-)-(2R,3R)-2,3-O-isopropylidene-2-C-methyl-D-erythrono-1,4-lactone (18465-72-0) → (3R,4R)-3,4-dihydroxy-3-methyl-4,5-dihydro-2(3H)-furanone (18465-71-9)

Guidance literature:

With trifluoroacetic acid; In water; at 0 - 20 ℃;

DOI:10.1016/j.tetlet.2006.09.156

Reference yield: 91.0%

(-)-(3R,4R)-acetic acid 4-hydroxy-4-methyl-5-oxotetrahydrofuran-3-yl ester (893418-49-0) → (3R,4R)-3,4-dihydroxy-3-methyl-4,5-dihydro-2(3H)-furanone (18465-71-9)

Guidance literature:

With potassium carbonate; In methanol; at 0 - 20 ℃;

DOI:10.1016/j.tetasy.2006.02.025

Reference yield: 72.0%

2-O-benzyl-2-C-methyl-D-erythrono-1,4-lactone (81347-85-5) → (3R,4R)-3,4-dihydroxy-3-methyl-4,5-dihydro-2(3H)-furanone (18465-71-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; acetic acid; for 8h;

DOI:10.1016/S0008-6215(00)81018-6

upstream raw materials:

2-O-benzyl-2-C-methyl-D-erythrono-1,4-lactone

(2R,3R)-3-t-butyldimethylsiloxy-2-hydroxy-2-methyl-γ-butyrolactone

(-)-(3R,4R)-acetic acid 4-hydroxy-4-methyl-5-oxotetrahydrofuran-3-yl ester

1-dimethylamino-3,4,5-trihydroxy-pentan-2-one

Downstream raw materials:

(-)-(3R,4R)-β-(3,4-dimethoxyphenyl)acrylic acid 4-hydroxy-4-methyl-5-oxotetrahydrofuran-3-yl ester

(2S,3S)-3-O-caffeyl-2,3,4-trihydroxy-2-methylbutan-1,4-olide