(s)-5-(Hydroxymethyl)dihydrofuran-2(3h)-one

Base Information

• Chemical Name: (s)-5-(Hydroxymethyl)dihydrofuran-2(3h)-one
• CAS No.: 32780-06-6
• Molecular Formula: C5H8O3
• Molecular Weight: 116.117
• Hs Code.: 29322090
• European Community (EC) Number: 680-050-3
• DSSTox Substance ID: DTXSID00954438
• Nikkaji Number: J736.724D
• Wikidata: Q76146068
• Mol file: 32780-06-6.mol

Synonyms:32780-06-6;(s)-5-(hydroxymethyl)dihydrofuran-2(3h)-one;(s)-5-hydroxymethyldihydrofuran-2-one;(S)-(+)-Dihydro-5-(hydroxymethyl)furanone;(5S)-5-(hydroxymethyl)oxolan-2-one;(S)-(+)-Dihydro-5-(hydroxymethyl)-2(3H)-furanone;(S)-(+)-gamma-Hydroxymethyl-gamma-butyrolactone;(s)-4-hydroxymethyl butyrolactone;2(3H)-Furanone, dihydro-5-(hydroxymethyl)-, (5S)-;(s)-5-(hydroxymethyl)-dihydrofuran-2(3h)-one;MFCD00066224;S-(+)-4-Hydroxymethyl-4-butanolide;(S)-(+)-2',3'-Dideoxyribonolactone;5-(Hydroxymethyl)dihydro-2(3H)-furanone #;(S)-5-Hydroxymethyl-2-oxotetrahydrofuran;(S)-4,5-Dihydro-5-hydroxymethyl-2(3H)-furanone;SCHEMBL283689;DTXSID00954438;BCP23415;GEO-04229;AKOS006238373;AKOS015856120;(5S)-5-(Hydroxymethyl)oxolane-2-one;AC-6630;CS-W002306;(S)-5-hydroxymethyl-dihydro-furan-2-one;AS-37601;A5857;H0958;(5S)-5-(hydroxymethyl)tetrahydro-2-furanone;(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran;(S)-(+)-5-Hydroxymethyltetrahydro-2-furanone;EN300-257939;(5S)-5-(hydroxymethyl)dihydrofuran-2(3H)-one;(5s)-dihydro-5-(hydroxymethyl)-2(3h)-furanone;(5S)-dihydro-5-(hydroxymethyl)furan-2(3H)-one;(S)-(+)-dihydro-5-hydroxymethyl-2(3H)furanone;Q-103502;(S)-(+)-4,5-Dihydro-5-hydroxymethyl-2(3H)-furanone;(S)-(+)-Dihydro-5-(hydroxymethyl)-2(3H)-furanone, 95%;(S)-gamma-Hydroxymethyl-gamma-butyrolactone, (S)-4,5-Dihydro-5-hydroxymethyl-2(3H)-furanone, (S)-5-Hydroxymethyl-2-oxotetrahydrofuran

Chemical Property of (s)-5-(Hydroxymethyl)dihydrofuran-2(3h)-one

Chemical Property:

• Appearance/Colour: Colorless to light yellow liquid
• Vapor Pressure: 6.02E-05mmHg at 25°C
• Melting Point: 72-74 °C
• Refractive Index: n20/D 1.471(lit.)
• Boiling Point: 308.9 °C at 760 mmHg
• PKA: 14.12±0.10(Predicted)
• Flash Point: 146 °C
• PSA: 46.53000
• Density: 1.224 g/cm³
• LogP: -0.31570
• Storage Temp.: 0-6°C
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 116.047344113
• Heavy Atom Count: 8
• Complexity: 99.8

Purity/Quality:

99.9% ^*data from raw suppliers

(S)-5-(Hydroxymethyl)dihydrofuran-2(3H)-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 23-24/25-37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)OC1CO
• Isomeric SMILES: C1CC(=O)O[C@@H]1CO
• Uses: (S)-(+)-Dihydro-5-(hydroxymethyl)-2(3H)-furanone can be used as a chiral synthon to synthesize:Potent nucleoside, acetylcholine, and (+)-muricatacin analogs.Mevinic acids, which are LDL cholesterol-lowering agents.Adenine based anti-HIV agent named β-F-ddA.

Technology Process of (s)-5-(Hydroxymethyl)dihydrofuran-2(3h)-one

There total 59 articles about (s)-5-(Hydroxymethyl)dihydrofuran-2(3h)-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: 100.0%

(2S)-tetrahydro-5-oxofuran-2-carboxylic acid (21461-84-7) → (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6)

Guidance literature:

With dimethylsulfide borane complex;

DOI:10.1016/S0957-4166(00)82115-1

Reference yield: 96.0%

(5S)-5-(hydroxymethyl)-5H-furan-2-one (78508-96-0) → (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 4h; Ambient temperature;

DOI:10.1016/S0040-4020(01)81204-7

Reference yield: 95.0%

S-4,5-O-isopropylidene-4,5-dihydroxy-2-ethoxycarbonylpentanoic acid ethyl ester (74500-40-6) → (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6)

Guidance literature:

With magnesium chloride; In N,N-dimethyl acetamide; water; for 20h; Heating;

upstream raw materials:

(2S)-tetrahydro-5-oxofuran-2-carboxylic acid

D-Glutamic acid

L-glutamic acid

1,6-anhydro-3,4-dideoxy-β-D-glycero-hexopyranos-2-ulose

Downstream raw materials:

(5S)-5-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)dihydrofuran-2(3H)-one

(5S)-5-[(benzyloxy)methyl]dihydrofuran-2(3H)-one

(4R)-pentane-1,4-diol

(S)-(+)-5-Aminomethyl-2-oxotetrahydrofuran hydrochloride

Refernces

• 1、 Figadere,Harmange,Laurens,Cave. "Stereospecific synthesis of (+)-muricatacin: A biologically active acetogenin derivative". . p. 7539 - 7542. Retrieved 1991.
• 2、 Flourat,Peru,Teixeira,Brunissen,Allais. "Chemo-enzymatic synthesis of key intermediates (S)-γ-hydroxymethyl-α,β-butenolide and (S)-γ-hydroxymethyl-γ-butyrolactone via lipase-mediated Baeyer-Villiger oxidation of levoglucosenone". . p. 404 - 412. Retrieved 2015.
• 3、 Eum, Heesung,Kazlauskas, Romas J.,Ha, Hyun-Joon. "Molecular basis for the enantio-and diastereoselectivity of burkholderia cepacia lipase toward γ-butyrolactone primary alcohols". . p. 3585 - 3599. Retrieved 2014.
• 4、 Kumar, Praveen,Rahman, Md. Ataur,Haque, Ashanul,Singh Yadav, Jhillu. "A transition metal-catalyzed enyne metathesis for the preparation of pyrrolizidine alkaloid core: Application towards the total synthesis of stemaphylline". . . Retrieved 2021/03/03.
• 5、 Banuelos-Sanchez, Guillermo,Franco-Montalban, Francisco,Tamayo, Juan A.. "NMR studies of pyrimidinic nucleosides derived from 2,3-dideoxy-d-ribose with inhibitory activity on LINE-1 mobility". . p. 118 - 125. Retrieved 2019/11/28.