Production Method 1

77697-15-5

52813-63-5

Reaction Conditions

Reference

A convenient synthesis of (R)-japonilure

Chattopadhyay, S.; Mamdapur, V. R.; Chadha, M. S., Synthetic Communications, 1990, 20(9), 1299-303

Production Method 2

73697-60-6

52813-63-5

Reaction Conditions

1.1 Catalysts: (SP-5-13)-(Acetato-κO)[[2,2′-[(1S,2S)-1,2-cyclohexanediylbis[(nitrilo-κN)methyli… Solvents: Water
1.2 Reagents: Trifluoroacetic acid
1.3 Solvents: Benzene

Reference

The conversion of racemic terminal epoxides into either (+)- or (-)-diol γ- and δ-lactones

Liu, Zhi-Yu; Ji, Jian-Xin; Li, Bo-Gang, Perkin 1, 2000, (20), 3519-3521

Production Method 3

56-86-0

52813-63-5

Reaction Conditions

1.1 Reagents: Hydrochloric acid

Reference

Total synthesis of the cytotoxic macrocycle (+)-hitachimycin

Smith, Amos B. III; Rano, Thomas A.; Chida, Noritaka; Sulikowski, Gary A.; Wood, John L., Journal of the American Chemical Society, 1992, 114(21), 8008-22

Production Method 4

53558-93-3

52813-63-5

Reaction Conditions

1.1 Reagents: Dimethyl sulfide ,  Borane Solvents: Tetrahydrofuran

Reference

Synthesis and Analysis of Libraries of Potential Flavour Compounds

Bang, Kyong-A., 2006, , ,

Production Method 5

53558-93-3

52813-63-5

Reaction Conditions

Reference

Alzheimer's therapy: an approach to novel muscarinic ligands based upon the naturally occurring alkaloid himbacine

Kozikowski, Alan P.; Fauq, Abdul H.; Miller, Jacqueline H.; McKinney, Michael, Bioorganic & Medicinal Chemistry Letters, 1992, 2(8), 797-802

Production Method 6

53558-94-4

52813-63-5

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Diglyme

Reference

Novel synthesis of L-hydroxyproline from D-glutamic acid

Eguchi, Chikahiko; Kakuta, Akio, Bulletin of the Chemical Society of Japan, 1974, 47(7), 1704-8

Production Method 7

6893-26-1

52813-63-5

Reaction Conditions

1.1 Reagents: Sodium nitrite ,  Sulfuric acid Solvents: Water ;  23 °C
1.2 Reagents: (Dimethyl sulfide)trihydroboron Solvents: Tetrahydrofuran ;  23 °C

Reference

Syntheses of sceptrins and nakamuric acid and insights into the biosyntheses of pyrrole-imidazole dimers

Wang, Xiaolei; Gao, Yang; Ma, Zhiqiang; Rodriguez, Rodrigo A.; Yu, Zhi-Xiang; et al, Organic Chemistry Frontiers, 2015, 2(8), 978-984

Production Method 8

53558-93-3

52813-63-5

Reaction Conditions

1.1 Reagents: (Dimethyl sulfide)trihydroboron Solvents: Tetrahydrofuran ;  15 min, 0 °C; 16 h, rt; rt → 0 °C
1.2 Solvents: Methanol ;  0 °C

Reference

Total Synthesis of Amphidinolide F

Valot, Gaelle; Regens, Christopher S.; O'Malley, Daniel P.; Godineau, Edouard; Takikawa, Hiroshi; et al, Angewandte Chemie, 2013, 52(36), 9534-9538

Production Method 9

53558-93-3

52813-63-5

Reaction Conditions

1.1 Reagents: (Dimethyl sulfide)trihydroboron Solvents: Tetrahydrofuran ;  -15 °C; overnight, rt
1.2 Reagents: Methanol ;  0 °C

Reference

Amphidinolides F and C2: An Odyssey in Total Synthesis

Ferrie, Laurent; Ciss, Ismaila; Fenneteau, Johan ; Vallerotto, Sara; Seck, Matar; et al, Journal of Organic Chemistry, 2022, 87(2), 1110-1123

Production Method 10

85428-31-5

52813-63-5

Reaction Conditions

1.1 Reagents: Trifluoroacetic acid ;  -10 °C

Reference

Dihydro-5-(hydroxymethyl)-2(3H)-furanone

Boukouvalas, John, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, 1, 1-4

Production Method 11

53558-93-3

52813-63-5

Reaction Conditions

1.1 Reagents: Dimethyl sulfide ,  Borane Solvents: Tetrahydrofuran

Reference

Synthesis and anti-viral activity of novel 3,6-dioxa- [3.2.0]bicyclonucleoside nucleotide analogs

Fang, Xingang, 2007, , 69(1),

Production Method 12

53716-82-8

52813-63-5

Reaction Conditions

1.1 Reagents: Hydrogen peroxide Solvents: Water ;  rt → 0 °C; 2 h, 0 °C → 50 °C

Reference

Dynamically tuning transient silicone polymer networks with hydrogen bonding

Yepremyan, Akop; Osamudiamen, Andrew; Brook, Michael A.; Feinle, Andrea, Chemical Communications (Cambridge, 2020, 56(88), 13555-13558

Production Method 13

128969-94-8

52813-63-5

Reaction Conditions

1.1 Reagents: Trifluoroacetic acid ;  20 min, -10 °C

Reference

Synthesis of enantiopure cyclopropyl esters from (-)-levoglucosenone

Stockton, Kieran P.; Greatrex, Ben W., Organic & Biomolecular Chemistry, 2016, 14(31), 7520-7528

Production Method 14

6893-26-1

52813-63-5

Reaction Conditions

1.1 Reagents: Sodium nitrite ,  Sulfuric acid Solvents: Water ;  15 h, rt
1.2 Reagents: (Dimethyl sulfide)trihydroboron Solvents: Tetrahydrofuran ;  1 h, rt

Reference

Design and synthesis of novel 2',3'-dideoxy-4'-selenonucleosides as potential antiviral agents

Jeong, Lak Shin; Choi, Yoo Na; Tosh, Dilip K.; Choi, Won Jun; Kim, Hea Ok; et al, Bioorganic & Medicinal Chemistry, 2008, 16(23), 9891-9897

Production Method 15

21461-84-7

52813-63-5

Reaction Conditions

1.1 Reagents: (Dimethyl sulfide)trihydroboron Solvents: Tetrahydrofuran ;  15 min, 0 °C; 16 h, rt; rt → 0 °C
1.2 Solvents: Methanol

Reference

Concise Total Syntheses of Amphidinolides C and F

Valot, Gaelle; Mailhol, Damien; Regens, Christopher S.; O'Malley, Daniel P.; Godineau, Edouard; et al, Chemistry - A European Journal, 2015, 21(6), 2398-2408

(R)-(-)-Dihydro-5-(hydroxymethyl)furanone Raw materials

• Oxiranepropanoic acid, methyl ester, (2S)-
• Ethyl (S)-(-)-4,5-epoxypentanoate
• ethyl 3-(oxiran-2-yl)propanoate
• 5-[(Benzyloxy)methyl]oxolan-2-one
• 2-Furancarbonylchloride, tetrahydro-5-oxo-, (2R)-
• L-Glutamic acid
• Cyrene
• D-Glutamic acid
• (2S)-5-oxooxolane-2-carboxylic acid
• (2R)-5-oxotetrahydrofuran-2-carboxylic acid

(R)-(-)-Dihydro-5-(hydroxymethyl)furanone Preparation Products

• (R)-(-)-Dihydro-5-(hydroxymethyl)furanone (52813-63-5)

• 1. Synthesis of enantiopure cyclopropyl esters from (?)-levoglucosenone
  Kieran P. Stockton,Ben W. Greatrex Org. Biomol. Chem. 2016 14 7520
• 2. First total synthesis of the marine natural products clavulolactones II and III
  Charlotte M. Miller,Tore Benneche,Marcus A. Tius Org. Biomol. Chem. 2015 13 4051

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Lactones Gamma butyrolactones

Introduction to (R)-(-)-Dihydro-5-(hydroxymethyl)furanone (CAS No. 52813-63-5)

(R)-(-)-Dihydro-5-(hydroxymethyl)furanone, with the chemical formula C?H?O?, is a significant compound in the field of pharmaceuticals and chemical synthesis. This chiral furanone derivative has garnered considerable attention due to its versatile applications and structural properties. The compound is characterized by its (R)-configuration, which plays a crucial role in its biological activity and reactivity. Its CAS number, 52813-63-5, uniquely identifies it in scientific literature and industrial applications.

The synthesis of (R)-(-)-Dihydro-5-(hydroxymethyl)furanone involves multi-step organic reactions, often requiring precise control over reaction conditions to achieve high enantiomeric purity. The presence of the hydroxymethyl group and the furanone ring makes it a valuable intermediate in the synthesis of more complex molecules. Recent advancements in catalytic methods have improved the efficiency of its production, making it more accessible for research and industrial purposes.

In the realm of pharmaceutical research, (R)-(-)-Dihydro-5-(hydroxymethyl)furanone has been explored for its potential biological activities. Studies have indicated that this compound exhibits promising properties as a precursor in the development of drugs targeting various diseases. Its structural motif is reminiscent of natural products known for their therapeutic effects, which has spurred interest in its pharmacological potential.

One of the most intriguing aspects of (R)-(-)-Dihydro-5-(hydroxymethyl)furanone is its role in asymmetric synthesis. The (R)-configuration imparted by the stereocenter at the carbon adjacent to the hydroxymethyl group allows for the selective synthesis of enantiomerically pure compounds. This is particularly important in pharmaceuticals, where the efficacy and safety of a drug are highly dependent on its enantiomeric purity. The ability to produce enantiomerically pure forms of complex molecules using (R)-(-)-Dihydro-5-(hydroxymethyl)furanone as a building block represents a significant advancement in synthetic chemistry.

Recent research has also highlighted the compound's utility in material science. The unique electronic and steric properties of furanones make them attractive candidates for developing novel materials with specific functionalities. For instance, derivatives of (R)-(-)-Dihydro-5-(hydroxymethyl)furanone have been investigated for their potential use in organic electronics, where their ability to form stable π-conjugated systems could lead to improvements in optoelectronic devices.

The biological activity of (R)-(-)-Dihydro-5-(hydroxymethyl)furanone has been further explored through computational studies and experimental assays. These investigations have revealed that the compound interacts with various biological targets, suggesting multiple potential therapeutic applications. For example, preliminary studies have shown that it may possess anti-inflammatory and antioxidant properties, which could be beneficial in treating chronic inflammatory diseases and oxidative stress-related disorders.

The synthetic pathways for producing (R)-(-)-Dihydro-5-(hydroxymethyl)furanone continue to evolve, driven by the demand for more efficient and sustainable methods. Green chemistry principles have influenced recent developments, with an emphasis on minimizing waste and reducing energy consumption. Catalytic hydrogenation and biocatalytic approaches have emerged as particularly promising strategies for achieving high yields and selectivity in the synthesis of this compound.

The role of computational chemistry in understanding the reactivity and properties of (R)-(-)-Dihydro-5-(hydroxymethyl)furanone cannot be overstated. Advanced computational methods allow researchers to predict molecular interactions and optimize reaction conditions with remarkable accuracy. This has led to new insights into how this compound behaves in different environments and how it can be tailored for specific applications.

In conclusion, (R)-(-)-Dihydro-5-(hydroxymethyl)furanone (CAS No. 52813-63-5) is a multifaceted compound with significant potential in pharmaceuticals, material science, and chemical synthesis. Its unique structural features and versatile reactivity make it a valuable building block for developing new drugs and materials. As research continues to uncover its full potential, this compound is poised to play an increasingly important role in advancing scientific knowledge and technological innovation.

• 15546-00-6(Hexanoic acid, 6-hydroxy-, (tetrahydro-2-furanyl)methyl ester)
• 494209-71-1(Formaldehyde, compd. with dihydro-5-(hydroxymethyl)-2(3H)-furanone(1:1))
• 39252-13-6(Oxolan-2-ylmethyl Nonanoate)
• 32780-06-6((5S)-5-(hydroxymethyl)oxolan-2-one)
• 105-02-2(Hexanedioic acid,1,6-bis[(tetrahydro-2-furanyl)methyl] ester)
• 134698-86-5(2(3H)-Furanone,dihydro-5-[(1R)-1-hydroxytridecyl]-, (5R)-)
• 105814-63-9(2(3H)-Furanone,dihydro-5-(1-hydroxyethyl)-)
• 58957-60-1(5-(1-Hydroxyethyl)oxolan-2-one)
• 87877-77-8(2(3H)-Furanone,dihydro-5-(1-hydroxyhexyl)-)
• 637-73-0(Dodecanoic acid,(tetrahydro-2-furanyl)methyl ester)