444286
(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:
Molecular Weight:
102.09
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
80588
Assay:
95%
Form:
liquid
Quality Level
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.)
functional group
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
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
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves
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Concise total synthesis of botryolide B
Mohapatra DK, et al.
Royal Society of Chemistry Advances, 4(16), 8335-8340 (2014)
Novel glucocorticoid antedrugs possessing a 21-(?-lactone) ring.
Angell RM, et al.
Journal of the Chemical Society. Perkin Transactions 1, 6, 831-839 (2002)
Novel glucocorticoid antedrugs possessing a 21-(γ-lactone) ring
Angell RM, et al.
Journal of the Chemical Society. Perkin Transactions 1, 4(6), 831-839 (2002)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 444286-1G | 04061837394584 |