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348902

Sigma-Aldrich

(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

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About This Item

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

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

SMILES string

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

InChI

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

InChI key

NSISJFFVIMQBRN-BYPYZUCNSA-N

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 Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

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

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Stereospecific synthesis of (+)-muricatacin: a biologically active acetogenin derivative
Figadere B, et al.
Tetrahedron Letters, 32(51), 7539-7542 (1991)
Blackwell, C.M. et al.
The Journal of Organic Chemistry, 57, 5597-5597 (1992)
Enantioselective synthesis of (R)-and (S)-5-dimethylaminomethyl-4, 5-dihydro-2 (3H)-furanone methobromide-constrained analogues of acetylcholine
Lehmann J and Pieper B
Tetrahedron Asymmetry, 3(12), 1537-1538 (1992)
Dihydro-5-(hydroxymethyl)-2(3H)-furanone
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
The Journal of Organic Chemistry, 58, 2557-2557 (1993)
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