(3R,4R,5R)-5-[(Benzoyloxy)methyl]-3-methyl-2-oxotetrahydrofuran-3,4-diyl dibenzoate | CAS No. 7392-74-7

(3R,4R,5R)-5-[(Benzoyloxy)methyl]-3-methyl-2-oxotetrahydrofuran-3,4-diyl dibenzoate

Basic Information

CAS Number

7392-74-7

Molecular Formula

C27H22O8

Molecular Weight

474.47 g/mol

AD

Basic Physical Properties

Melting Point

131-133°C

CC1(C(C(OC1=O)COC(=O)C2=CC=CC=C2)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4

InChI

InChI=1S/C27H22O8/c1-27(35-25(30)20-15-9-4-10-16-20)22(34-24(29)19-13-7-3-8-14-19)21(33-26(27)31)17-32-23(28)18-11-5-2-6-12-18/h2-16,21-22H,17H2,1H3/t21-,22-,27-/m1/s1

InChIKey

KOELERLPRQKGLG-VHFRWLAGSA-N

LogP

3.6101000000000028

Topological Polar Surface Area

105.20000000000002 Ų

Hydrogen Bond Donor/Acceptor

0 / 8

Complexity

776

Synonyms & References

English

  • MFCD07369678
  • (3R,4R,5R)-5-((Benzoyloxy)methyl)-3-methyl-2-oxotetrahydrofuran-3,4-diyldibenzoate
  • 7392-74-7
  • AKOS016009695
  • CS-0009553
  • [(2R,3R,4R)-3,4-dibenzoyloxy-4-methyl-5-oxooxolan-2-yl]methyl benzoate
  • DTXSID00563387
  • (3R,4R,5R)-4-(BENZOYLOXY)-5-[(BENZOYLOXY)METHYL]-3-METHYL-2-OXOOXOLAN-3-YL BENZOATE
  • 2,3,5-Tri-O-benzoyl-2-C-methyl-D-ribonic-1,4-lactone
  • SS-5258
  • [(2R,3R,4R)-3,4-dibenzoyloxy-4-methyl-5-oxo-tetrahydrofuran-2-yl]methyl benzoate
  • SCHEMBL1825686
  • (3R,4R,5R)-5-((Benzoyloxy)methyl)-3-methyl-2-oxotetrahydrofuran-3,4-diyl dibenzoate
  • 2,3,5-Tri-O-benzoyl-2-C-methyl-D-ribonic acid-1,4-lactone
  • 93636-17-0
  • rel-(3R,4R,5R)-5-((Benzoyloxy)methyl)-3-methyl-2-oxotetrahydrofuran-3,4-diyl dibenzoate
  • W17273
  • (2R,3R,4R)-4-(Benzoyloxy)-2-[(benzoyloxy)methyl]-4-methyl-5-oxooxolan-3-yl benzoate (non-preferred name)
  • W-203686
  • 2,3,5-Tri-O-benzoyl-
  • 2,3,4,6-TETRA-O-ACETYL-1-O-TRICHLOROACETIMIDOYL-
  • D-ribo-Pentonicacid, 2-C-methyl-, g-lactone, tribenzoate (7CI)
  • Ribonic acid, 2-C-methyl-, g-lactone, tribenzoate, D- (8CI)

MDL Number

MFCD07369678

FAQ

What are the physical and chemical properties of (3R,4R,5R)-5-[(Benzoyloxy)methyl]-3-methyl-2-oxotetrahydrofuran-3,4-diyl dibenzoate (CAS: 7392-74-7)?

(3R,4R,5R)-5-[(Benzoyloxy)methyl]-3-methyl-2-oxotetrahydrofuran-3,4-diyl dibenzoate (CAS: 7392-74-7) is a crystalline compound with a molecular weight of approximately 508.4 g/mol. It has a low solubility in water, but is soluble in organic solvents such as ethanol and acetone. The compound is moderately reactive, particularly with nucleophiles and reducing agents. It may undergo hydrolysis under basic conditions. This compound is used in various applications, including pharmaceuticals and polymer synthesis.

How is (3R,4R,5R)-5-[(Benzoyloxy)methyl]-3-methyl-2-oxotetrahydrofuran-3,4-diyl dibenzoate (CAS: 7392-74-7) typically synthesized?

(3R,4R,5R)-5-[(Benzoyloxy)methyl]-3-methyl-2-oxotetrahydrofuran-3,4-diyl dibenzoate (CAS: 7392-74-7) can be synthesized via a multi-step process, starting from the diol and benzoyl chloride. The key steps involve esterification, ring closure, and benzoate formation. Common solvents used include dichloromethane, and the reaction is typically catalyzed by a Lewis acid like aluminum chloride. The overall yield is moderate, around 60-70%, with high selectivity for the desired product.

What industries use (3R,4R,5R)-5-[(Benzoyloxy)methyl]-3-methyl-2-oxotetrahydrofuran-3,4-diyl dibenzoate (CAS: 7392-74-7)?

(3R,4R,5R)-5-[(Benzoyloxy)methyl]-3-methyl-2-oxotetrahydrofuran-3,4-diyl dibenzoate (CAS: 7392-74-7) is utilized in a variety of industries, particularly in pharmaceuticals, where it serves as a precursor for the synthesis of drugs. It also finds applications in polymer chemistry, where it can be used to create functional polymers with specific properties. Additionally, it is used in the development of sensors and semiconductors, leveraging its unique chemical structure and reactivity.

What precautions should be taken when handling (3R,4R,5R)-5-[(Benzoyloxy)methyl]-3-methyl-2-oxotetrahydrofuran-3,4-diyl dibenzoate (CAS: 7392-74-7)?

When handling (3R,4R,5R)-5-[(Benzoyloxy)methyl]-3-methyl-2-oxotetrahydrofuran-3,4-diyl dibenzoate (CAS: 7392-74-7), it is crucial to follow standard safety protocols. Wear appropriate personal protective equipment (PPE), including gloves, goggles, and a lab coat. Work in a well-ventilated area, preferably in a fume hood, to minimize exposure to the compound and its vapors. Ensure proper storage in a cool, dry place away from sources of heat and moisture. Spills should be cleaned up using appropriate methods, and always consult the safety data sheet (SDS) for detailed instructions and emergency procedures.

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