Skip to Content
Merck
CN

348902

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

95%

Synonym(s):

(S)-γ-Hydroxymethyl-γ-butyrolactone, (S)-4,5-Dihydro-5-hydroxymethyl-2(3H)-furanone, (S)-5-Hydroxymethyl-2-oxotetrahydrofuran

Sign In to View Organizational & Contract Pricing.

Select a Size

About This Item

Empirical Formula (Hill Notation):
C5H8O3
CAS Number:
32780-06-6
Molecular Weight:
116.12
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
24861633
MDL number:
MFCD00066224
Beilstein/REAXYS Number:
1680284

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

InChI

1S/C5H8O3/c6-3-4-1-2-5(7)8-4/h4,6H,1-3H2/t4-/m0/s1

SMILES string

OC[C@@H]1CCC(=O)O1

InChI key

NSISJFFVIMQBRN-BYPYZUCNSA-N

assay

95%

form

liquid

optical activity

[α]20/D +56°, c = 3 in chloroform

optical purity

ee: 98% (GLC)

refractive index

n20/D 1.471 (lit.)

bp

110-115 °C/0.2 mmHg (lit.)

density

1.237 g/mL at 25 °C (lit.)

storage temp.

2-8°C

General description

Dihydro-5-(hydroxymethyl)-2(3H)-furanone is a chiral building block widely used in the synthesis of many natural products and few biologically significant compounds like anti-HIV dideoxynucleosides. It is also used in the synthesis of optically active ligands.

Application

(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.

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
81896KJV
81896KJ
03929EJ
06931MH
09716PE

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

A concise synthesis of anti-viral agent F-ddA, starting from (S)-dihydro-5-(hydroxymethyl)-2 (3H)-furanone
Choudhury A, et al.
Tetrahedron Letters, 44(2), 247-250 (2003)
Enantio-and diastereoisomers of 2, 4-dimethoxy-5-(2, 3-dideoxy-5-O-tritylribofuranosyl) pyrimidine. 2′, 3′-Dideoxy pyrimidine C-nucleosides by palladium-mediated glycal-aglycon coupling
Zhang HC and Daves Jr GD
The Journal of Organic Chemistry, 58(9), 2557-2560 (1993)
Stereospecific synthesis of (+)-muricatacin: a biologically active acetogenin derivative
Figadere B, et al.
Tetrahedron Letters, 32(51), 7539-7542 (1991)
Dihydro-5-(hydroxymethyl)-2(3H)-furanone
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
Total synthesis of dihydromevinolin and a series of related 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitors
Blackwell CM, et al.
The Journal of Organic Chemistry, 57(21), 5596-5606 (1992)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service