462233
D-Galactal
95%
Synonym(s):
1,5-Anhydro-2-deoxy-D-lyxo-hex-1-enitol
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About This Item
Empirical Formula (Hill Notation):
C6H10O4
CAS Number:
Molecular Weight:
146.14
UNSPSC Code:
12352201
NACRES:
NA.22
PubChem Substance ID:
EC Number:
244-264-7
Beilstein/REAXYS Number:
81690
MDL number:
InChI key
YVECGMZCTULTIS-HSUXUTPPSA-N
InChI
1S/C6H10O4/c7-3-5-6(9)4(8)1-2-10-5/h1-2,4-9H,3H2/t4-,5-,6-/m1/s1
SMILES string
OC[C@H]1OC=C[C@@H](O)[C@H]1O
assay
95%
optical activity
[α]22/D −21.5°, c = 1.2 in methanol
mp
99-103 °C (lit.)
storage temp.
2-8°C
Application
Important building block for both solution- and solid-phase synthesis of oligosaccharides.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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Aditi Agarwal et al.
The Journal of organic chemistry, 69(18), 6137-6140 (2004-09-18)
Perchloric acid supported on silica gel acts as an excellent reagent system in converting glucals into 2,3-unsaturated-O-glucosides in good to excellent yields in short reaction time with good alpha selectivity. Primary, secondary, and allylic alcohols, phenols, and thiols react with
Chi-Li Chen et al.
Organic letters, 11(2), 409-412 (2009-01-09)
With focus on the steric effects present in the transition states for the [3,3]-sigmatropic rearrangement, the substrate 5 has been designed to improve the overall stereoselectivity of the Ireland-Claisen rearrangement. Experimentally, it has been found that (1) only Z-6 rearranges
Jürgen Geiger et al.
The Journal of organic chemistry, 72(12), 4367-4377 (2007-05-17)
A 3,4-O-unprotected galactal derivative having bulky 6-O-TIPS protection (compound 2) could be regioselectively 3-O-glycosylated with O-(galactopyranosyl) trichloroacetimidates; depending on the protecting group pattern stereoselectively alpha- and beta-linked disaccharides were obtained. With O-(2-azido-2-deoxyglucopyransyl) trichloroacetimidate as donor (compound 10A), glycosylation of 2
Feiqing Ding et al.
Organic letters, 13(4), 652-655 (2011-01-20)
A highly efficient synthesis of L-ristosamine and L-epi-daunosamine glycosides via BF(3)·OEt(2) promoted tandem hydroamination/glycosylation of 3,4-di-O-acetyl-6-deoxy-L-glucal and L-galactal has been developed. The new method proceeds in a completely stereocontrolled manner within a short reaction time. Preparation of a library of
Alessandra Bartolozzi et al.
The Journal of organic chemistry, 68(22), 8529-8533 (2003-10-25)
A nonclassical, totally stereoselective synthesis of orthogonally protected 1,3-disaccharides is reported. Enantiomerically pure beta-keto-delta-lactones, efficiently obtained from glucal and galactal, are transformed into electron-poor heterodienes and chemo-, regio-, and stereoselectively cycloadded to glycals as electron-rich dienophiles, to directly afford 2-thiodisaccharides.
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