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444286

Sigma-Aldrich

(R)-(+)-α-Hydroxy-γ-butyrolactone

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

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C4H6O3
CAS Number:
56881-90-4
Molecular Weight:
102.09
Beilstein/REAXYS Number:
80588
MDL number:
MFCD00211246
UNSPSC Code:
12352005
PubChem Substance ID:
24868111
NACRES:
NA.22

assay

95%

form

liquid

optical activity

[α]23/D +66°, c = 1.15 in chloroform

optical purity

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.)

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

Application

(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

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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