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309753

Sigma-Aldrich

(R)-(−)-3-Hydroxytetrahydrofuran

98%

Synonym(s):

(R)-(-)-Tetrahydro-3-furanol

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About This Item

Empirical Formula (Hill Notation):
C4H8O2
CAS Number:
86087-24-3
Molecular Weight:
88.11
MDL number:
MFCD00067101
UNSPSC Code:
12352005
PubChem Substance ID:
24858751
NACRES:
NA.22

Assay

98%

form

liquid

optical activity

[α]20/D −18°, c = 2.4 in methanol

refractive index

n20/D 1.45 (lit.)

bp

181 °C (lit.)

density

1.097 g/mL at 25 °C (lit.)

functional group

ether
hydroxyl

SMILES string

O[C@@H]1CCOC1

InChI

1S/C4H8O2/c5-4-1-2-6-3-4/h4-5H,1-3H2/t4-/m1/s1

InChI key

XDPCNPCKDGQBAN-SCSAIBSYSA-N

Application

(R)-(-)-3-Hydroxytetrahydrofuran may be used as building block in the synthesis of potent HIV protease inhibitors.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

179.6 °F - closed cup

Flash Point(C)

82 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000346987
0000346987
0000268840
0000183712
SHBM6158

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Diethyl zinc catalyzed diastereoselective addition of ketenes to (S)-(+)-3-hydroxytetrahydrofuran.
Tandon VK.
Tetrahedron Letters, 42(34), 5985-5987 (2001)
Angle-Resolved Photoelectron Spectroscopy of Randomly Oriented 3-Hydroxytetrahydrofuran Enantiomers.
Giardini A, et al.
ChemPhysChem, 6(6), 1164-1168 (2005)
Matt Hrapchak et al.
Journal of labelled compounds & radiopharmaceuticals, 57(12), 687-694 (2014-10-22)
Empagliflozin, (2S,3R,4R,5S,6R)-2-[4-chloro-3-[[4-[(3S)-oxolan-3-yl]oxyphenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol was recently approved by the FDA for the treatment of chronic type 2 diabetes mellitus. Herein, we report the synthesis of carbon-13 and carbon-14 labeled empagliflozin. Carbon-13 labeled empagliflozin was prepared in five steps and in 34% overall

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