5-O-Benzyl-2,3-O-isopropylidene-D-ribono-1,4-lactone | CAS No. 85846-80-6

5-O-Benzyl-2,3-O-isopropylidene-D-ribono-1,4-lactone

Basic Information

CAS Number

85846-80-6

Molecular Formula

C15H18O5

Molecular Weight

278.3 g/mol

AD

Basic Physical Properties

O=C(O[C@@H]1COCC2=CC=CC=C2)[C@H]3[C@@H]1OC(C)(C)O3

InChI

InChI=1S/C15H18O5/c1-15(2)19-12-11(18-14(16)13(12)20-15)9-17-8-10-6-4-3-5-7-10/h3-7,11-13H,8-9H2,1-2H3/t11-,12-,13-/m1/s1

InChIKey

HTBWOOVHGLNZBX-JHJVBQTASA-N

LogP

1.6486999999999998

Topological Polar Surface Area

53.99000000000001 Ų

Hydrogen Bond Donor/Acceptor

0 / 5

Complexity

361

Synonyms & References

English

  • 5-O-Benzyl-2,3-O-isopropylidene-D-ribono-1,4-lactone
  • (3aR,6R,6aR)-6-[(Benzyloxy)methyl]-2,2-dimethyldihydrofuro[3,4-d] [1,3]dioxol-4(3aH)-one (non-preferred name)
  • (3aR,6R,6aR)-6-(benzyloxyMethyl)-2,2-diMethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one
  • (3aR,6R,6aR)-6-((benzyloxy)methyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one
  • 2-O,3-O-Isopropylidene-5-O-benzyl-D-ribo-pentonic acid 1,4-lactone

MDL Number

MFCD18782001

FAQ

What are the physical and chemical properties of 5-O-Benzyl-2,3-O-isopropylidene-D-ribono-1,4-lactone (CAS: 85846-80-6)?

5-O-Benzyl-2,3-O-isopropylidene-D-ribono-1,4-lactone (CAS: 85846-80-6) is a white crystalline solid with a molecular weight of approximately 286.3 g/mol. It has a low solubility in water but is soluble in organic solvents like ethanol and acetone. The compound shows moderate reactivity with hydroxyl compounds and exhibits stability under neutral conditions.

How is 5-O-Benzyl-2,3-O-isopropylidene-D-ribono-1,4-lactone (CAS: 85846-80-6) typically synthesized?

5-O-Benzyl-2,3-O-isopropylidene-D-ribono-1,4-lactone is commonly synthesized through a condensation reaction between D-ribonolactone and benzyl bromide in the presence of a phosphine-based organocatalyst. The reaction yields a high purity product with good selectivity and moderate yield under mild conditions.

What industries use 5-O-Benzyl-2,3-O-isopropylidene-D-ribono-1,4-lactone (CAS: 85846-80-6)?

5-O-Benzyl-2,3-O-isopropylidene-D-ribono-1,4-lactone (CAS: 85846-80-6) is primarily utilized in the pharmaceutical industry for the synthesis of certain biologically active compounds. It also finds application in the production of functional polymers and as a reagent in organic synthesis for its structural features.

What precautions should be taken when handling 5-O-Benzyl-2,3-O-isopropylidene-D-ribono-1,4-lactone (CAS: 85846-80-6)?

When handling 5-O-Benzyl-2,3-O-isopropylidene-D-ribono-1,4-lactone (CAS: 85846-80-6), it is crucial to use appropriate personal protective equipment (PPE) such as gloves and safety glasses. It should be stored in a cool, dry place away from direct sunlight. Spills should be cleaned up immediately according to a well-prepared safety data sheet (SDS) to ensure safety.

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