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Merck
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文件

348902

Sigma-Aldrich

(S)-5-羟甲基二氢呋喃-2-酮

95%

别名:

(S)-γ-羟甲基-γ-丁内酯, (S)-4,5-二氢-5-羟甲基-2(3H)-呋喃酮, (S)-5-羟甲基-2-氧代四氢呋喃

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About This Item

经验公式（希尔记法）:
C5H8O3
CAS号:
32780-06-6
分子量:
116.12
Beilstein:
1680284
MDL號碼:
MFCD00066224
分類程式碼代碼:
12352005
PubChem物質ID:
24861633
NACRES:
NA.22

化驗

95%

形狀

liquid

光學活性

[α]20/D +56°, c = 3 in chloroform

光學純度

ee: 98% (GLC)

折射率

n20/D 1.471 (lit.)

bp

110-115 °C/0.2 mmHg (lit.)

密度

1.237 g/mL at 25 °C (lit.)

儲存溫度

2-8°C

SMILES 字串

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 密鑰

NSISJFFVIMQBRN-BYPYZUCNSA-N

一般說明

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.

應用

(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.

儲存類別代碼

10 - Combustible liquids

水污染物質分類（WGK）

WGK 3

閃點（°F）

235.4 °F - closed cup

閃點（°C）

113 °C - closed cup

個人防護裝備

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

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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)
Blackwell, C.M. et al.
The Journal of Organic Chemistry, 57, 5597-5597 (1992)
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)
Dihydro-5-(hydroxymethyl)-2(3H)-furanone
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
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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