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Merck
모든 사진(1)

주요 문서

444286

Sigma-Aldrich

(R)-(+)-α-Hydroxy-γ-butyrolactone

95%, optical purity ee: 98% (GLC)

동의어(들):

(R)-4,5-Dihydro-3-hydroxy-2(3H)-furanone

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About This Item

실험식(Hill 표기법):
C4H6O3
CAS Number:
Molecular Weight:
102.09
Beilstein:
80588
MDL number:
UNSPSC 코드:
12352005
PubChem Substance ID:
NACRES:
NA.22

Quality Level

분석

95%

양식

liquid

광학 활성

[α]23/D +66°, c = 1.15 in chloroform

광학 순도

ee: 98% (GLC)

refractive index

n20/D 1.467 (lit.)

bp

133 °C/10 mmHg (lit.)

density

1.309 g/mL at 25 °C (lit.)

작용기

ester
hydroxyl

SMILES string

O[C@@H]1CCOC1=O

InChI

1S/C4H6O3/c5-3-1-2-7-4(3)6/h3,5H,1-2H2/t3-/m1/s1

InChI key

FWIBCWKHNZBDLS-GSVOUGTGSA-N

애플리케이션

(R)-(+)-α-Hydroxy-γ-butyrolactone can be used as a starting material to synthesize:
  • δ-Azaproline by reacting with benzyloxycarbonyl aminophthalimide via Mitsunobu reactions.
  • Homochiral (R)-2,4-dihydroxybutyramide seco-pseudonucleoside reagents.
  • Botryolide B via esterification and ring-closing metathesis reaction.
  • Pregnane derivatives containing γ-butyrolactones as potential glucocorticoid agonists.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

개인 보호 장비

Eyeshields, Gloves


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문서 라이브러리 방문

Novel glucocorticoid antedrugs possessing a 21-(?-lactone) ring.
Angell RM, et al.
Journal of the Chemical Society. Perkin Transactions 1, 6, 831-839 (2002)
Concise total synthesis of botryolide B
Mohapatra DK, et al.
Royal Society of Chemistry Advances, 4(16), 8335-8340 (2014)
Xiaohui Gou et al.
Frontiers in physiology, 11, 686-686 (2020-07-17)
Dentin sialoprotein (DSP), the NH2-terminal fragment of dentin sialophosphoprotein (DSPP), is essential for dentin formation and further processed into small fragments inside the odontoblasts. Gelatinases, including matrix metalloproteinases 9 (MMP9) and MMP2, were able to cleave DSP(P) in tooth structures.
Natalia N Dioubankova et al.
Organic letters, 4(26), 4607-4610 (2002-12-20)
[reaction: see text] Two series of seco-pseudonucleoside synthons were synthesized from (R)-(+)-alpha-hydroxy-gamma-butyrolactone and (R)-(-)-pantolactone by aminolysis, side-chain protection, dimethoxytritylation, and phosphitylation or solid-phase attachment. The phosphoramidites and solid supports were used in automated DNA synthesis to prepare oligonucleotides modified with

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