5-(Hydroxymethyl)-2(5H)-furanone

Base Information

• Chemical Name: 5-(Hydroxymethyl)-2(5H)-furanone
• CAS No.: 78508-96-0
• Molecular Formula: C5H6O3
• Molecular Weight: 114.101
• Hs Code.: 2932209090
• DSSTox Substance ID: DTXSID70276396
• Nikkaji Number: J715.014H
• Mol file: 78508-96-0.mol

Synonyms:5-(Hydroxymethyl)-2(5H)-furanone;10374-60-4;2-(hydroxymethyl)-2H-furan-5-one;2(5H)-Furanone, 5-(hydroxymethyl)-;L-ERYTHRO-ASCORBATE;(S)-5-Hydroxymethyl-2(5H)-furanone;(S)-5-Hydroxymethyl-2[5H]-furanone;erythro-ascorbate;5-(hydroxymethyl)-2,5-dihydrofuran-2-one;SCHEMBL811051;5-hydroxymethyl-2(5h)-furanone;DTXSID70276396;CHEBI:183113;2-(hydroxymethyl)-2H-uran-5-one;AKOS015913945;SB45317;FT-0605221;FT-0771760;EN300-216682

Chemical Property of 5-(Hydroxymethyl)-2(5H)-furanone

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 41-43 °C(lit.)
• Refractive Index: 1.502
• Boiling Point: 334.754 °C at 760 mmHg
• PKA: 13.51±0.10(Predicted)
• Flash Point: 166.808 °C
• PSA: 46.53000
• Density: 1.295 g/cm³
• LogP: -0.53970
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Solubility.: Chloroform (Slightly), Methanol (Slightly), Water (Sparingly)
• Water Solubility.: Slightly soluble in water.
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 114.031694049
• Heavy Atom Count: 8
• Complexity: 128

Purity/Quality:

99.5% ^*data from raw suppliers

(S)-(-)-5-hydroxymethyl-2(5H)-furanone ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=O)OC1CO
• Uses: (S)-(-)-5-Hydroxymethyl-2(5H)-furanone is used in the preparation of partially saturated heterocycles via a diastereoselective ring chain formation. It is also used in the synthesis of (1R,3S)-cis-chrysanthemic acid. (S)-(?)-5-Hydroxymethyl-2(5H)-furanone can be used as a starting material in the preparation of:Partially saturated heterocycles via a diastereoselective ring chain formation.A natural product named (+)-muscarine.3′-Ethynylthymidine as a possible antiviral agent.

Technology Process of 5-(Hydroxymethyl)-2(5H)-furanone

There total 41 articles about 5-(Hydroxymethyl)-2(5H)-furanone 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: 97.0%

methyl (2Z)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acrylate (81703-94-8) → (5S)-5-(hydroxymethyl)-5H-furan-2-one (78508-96-0)

Guidance literature:

With sulfuric acid; In methanol; at 23 ℃; for 2h;

DOI:10.1021/jo049156y

Reference yield: 95.0%

ethyl (R,Z)-3-(2′,2′-dimethyl-1′,3′-dioxolan-4′-yl)acrylate (36326-38-2,64520-58-7,91057-97-5,91926-90-8,104321-62-2,124818-64-0,128525-67-7,128525-69-9,104321-63-3,917877-01-1) → (5S)-5-(hydroxymethyl)-5H-furan-2-one (78508-96-0)

Guidance literature:

With sulfuric acid; In methanol; for 0.5h; Ambient temperature;

Reference yield: 90.0%

ethyl (Z)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate (91926-90-8,917877-01-1) → (5S)-5-(hydroxymethyl)-5H-furan-2-one (78508-96-0)

Guidance literature:

With hydrogenchloride;

DOI:10.1016/S0040-4039(00)82864-6

upstream raw materials:

(-)-(S)-5-acetyloxymethyl-2(5H)-furanone

tert-butyl 6-O-acetyl-3,4-dideoxy-α-D-glycero-hex-3-enopyranosid-2-ulose

levoglucosenone

2-Bromo-2-deoxy-D-arabinono-γ-lactone

Downstream raw materials:

(4S,5S)-4-benzylamino-5-((t-butyldiphenylsilyl)oxymethyl)dihydro-2-(3H)furanone

4(R)-azido-5(S)-<(tert-butyldiphenylsilyl)oxymethyl>-3,4-dihydro-5H-furan-2-one

alpha-3'-azido-2',3'-dideoxythymidine

(S)-5-tosyloxypentan-4-olide

Refernces

• 1、 Baskaran,Vasu,Prasad, Ram,Kodukulla,Trivedi, Girish K.,Chandrasekhar. "1,3-Dipolar cycloaddition reaction of α,β-unsaturated esters and lactones with diazomethane". . p. 4515 - 4526. Retrieved 1996.
• 2、 Ondrus, Vladimir,Orsag, Michal,Fisera, L'ubor,Pronayova, Nad'a. "Stereoselectivity of N-benzyl-C-ethoxycarbonyl nitrone cycloaddition to (S)-5-hydroxymethyl-2(5H)-furanone and its derivatives". . p. 10425 - 10436. Retrieved 1999.
• 3、 Moreaux, Maxime,Bonneau, Guillaume,Peru, Aurélien,Brunissen, Fanny,Janvier, Marine,Haudrechy, Arnaud,Allais, Florent. "High-Yielding Diastereoselective syn-Dihydroxylation of Protected HBO: An Access to D-(+)-Ribono-1,4-lactone and 5-O-Protected Analogues". supporting information. p. 1600 - 1604. Retrieved 2019/01/14.
• 4、 -. "METHOD FOR CONVERTING LEVOGLUCOSENONE INTO 4-HYDROXYMETHYL BUTYROLACTONE AND 4-HYDROXYMETHYL BUTENOLIDE WITHOUT USING ANY ORGANIC SOLVENT AND CATALYST". Paragraph 0052-0056; 0057-0058; 0081-0084; 0085-0086. . Retrieved 2019/07/23.