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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.[1]

Application

(S)-(+)-Dihydro-5-(hydroxymethyl)-2(3H)-furanone can be used as a chiral synthon to synthesize:
  • Potent nucleoside, acetylcholine, and (+)-muricatacin analogs.[2][3][4]
  • Mevinic acids, which are LDL cholesterol-lowering agents.[3][5]
  • Adenine based anti-HIV agent named β-F-ddA.[6]

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

348902-250MG:
348902-1G:
348902-BULK:
348902-VAR:

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Certificates of Analysis (COA)

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

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Blackwell, C.M. et al.
The Journal of Organic Chemistry, 57, 5597-5597 (1992)
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)
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)
Stereospecific synthesis of (+)-muricatacin: a biologically active acetogenin derivative
Figadere B, et al.
Tetrahedron Letters, 32(51), 7539-7542 (1991)
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)
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