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About This Item
Empirical Formula (Hill Notation):
C5H10O5
CAS Number:
Molecular Weight:
150.13
Beilstein:
1723085
EC Number:
MDL number:
UNSPSC Code:
12352201
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
Assay
98%
form
powder
optical activity
[α]20/D +103°, c = 1 in H2O
mp
160-163 °C (lit.)
SMILES string
OC[C@H](O)[C@H](O)[C@@H](O)C=O
InChI
1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h1,3-5,7-10H,2H2/t3-,4-,5+/m0/s1
InChI key
PYMYPHUHKUWMLA-VAYJURFESA-N
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Related Categories
Application
L-(+)-Arabinose is used as a key starting material in the total synthesis of (+)-ambruticin, zaragozic acid A, (−)-radicamine B and (+)-herbarumin I.
Biochem/physiol Actions
L-Arabinose is the naturally occurring isomer and is a constituent of plant polysaccharides. Most bacteria contain an inducible arabinose operon that codes for a series of enzymes and transporters that allows L-arabinose to be used as the sole carbon source in microbial culture.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Total synthesis of (-)-radicamine B.
Gurjar, Mukund K et al.
Tetrahedron Letters, 47(39), 6979-6981 (2006)
Stereoselective total synthesis of zaragozic acid A based on an acetal [1, 2] Wittig rearrangement.
Tomooka, Katsuhiko et al.
Angewandte Chemie (International Edition in English), 39(24), 4502-4505 (2000)
Total synthesis of (+)-herbarumin I via intermolecular Nozaki-Hiyama-Kishi reaction.
Sabino, Adao Aparecido and Pilli, Ronaldo A
Tetrahedron Letters, 43(15), 2819-2821 (2002)
Total synthesis of ambruticin.
Eun Lee et al.
Angewandte Chemie (International ed. in English), 41(1), 176-178 (2002-12-20)
Catarina M S S Neves et al.
Frontiers in chemistry, 7, 459-459 (2019-07-19)
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