Page 29 of 31
The Journal of Organic Chemistry
1
2
3
4
5
6
(9) Lin, T.-H.; Kováč, P.; Glaudemans, C. P. J. Improved synthesis of the 2-, 3-, and 4-
deoxy derivatives from methyl -D-galactopyranoside. Carbohydr. Res. 1989, 188,
228-238.
(10) Huang, G. L.; Dai, Y. P. Solid-Phase Synthesis of Allosamidin. Synlett 2010, 1554-
1556.
(11) Mori, T.; Ichyansi, T.; Kondo, H.; Tokkunasa, T.; Oda, T.; Munakata, T. Studies on
new antibiotic lividomycins. J. Antibiot. 1971, 24, 339–346.
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
(12) Miyashita, M.; Chida, N.; Yoshikohsi, A. Synthesis of the precursor of (+)-
thienamycin utilizing D-glucosamine. J. Chem. Soc., Chem. Commun. 1982, 1354–
1356.
(13) McEvoy, F. J.; Weiss, M. J.; Baker, B. R. The Synthesis of 9-(2-Amino-2-deoxy--D-
allopyranosyl)-6-dimethylaminopurine, an Analog of the Aminonucleoside Derived
from Puromycin. J. Am. Chem. Soc. 1960, 82, 205-209.
(14) Kandula, Mahesh. Compositions and Methods for the Treatment of Inflammation. U.S.
Patent 2015/0148306 A1. 2015.
(15) (a) Jäger, M.; Minnaard, A. J. Regioselective modification of unprotected glycosides.
Chem. Commun. 2016, 52, 656-664. (b) Dimakos, V.; Garrett, G. E.; Taylor, M. S.
Site-Selective, Copper-Mediated O-Arylation of Carbohydrate Derivatives. J. Am.
Chem. Soc. 2017, 139, 15515-15521. (c) Wei, X.-F.; Shimizu, Y.; Kanai, M. An
Expeditious Synthesis of Sialic Acid Derivatives by Copper (I)-Catalyzed
Stereodivergent Propargylation of Unprotected Aldoses. ACS Cent. Sci. 2016, 2, 21-
26.
(16) Jäger, M.; Hartmann, M.; de Vries, J. G.; Minnaard, A. J. Catalytic regioselective
oxidation of glycosides. Angew. Chem. Int. Ed. Engl. 2013, 52, 7809-12.
(17) Armenise, N.; Tahiri, N.; Eisink, N. N. H. M.; Denis, M.; Jäger, M.; De Vries, J. G.;
Witte, M. D.; Minnaard, A. J. Deuteration enhances catalyst lifetime in palladium-
catalysed alcohol oxidation. Chem. Commun. 2016, 52, 2189-2191.
(18) Eisink, N. N. H. M.; Lohse, J.; Witte, M. D.; Minnaard, A. J. Regioselective oxidation
of unprotected 1,4 linked glucans. Org. Biomol. Chem. 2016, 14, 4859-4864.
(19) Jumde, V. R.; Eisink, N. N. H. M.; Witte, M. D.; Minnaard, A. J. C3 Epimerization of
Glucose, via Regioselective Oxidation and Reduction. J. Org. Chem. 2016, 81, 11439-
11443.
(20) Eisink, N. N. H. M.; Witte, M. D.; Minnaard, A. J. Regioselective Carbohydrate
Oxidations: A Nuclear Magnetic Resonance (NMR) Study on Selectivity, Rate, and
Side-Product Formation. ACS Catal. 2017, 7, 1438-1445.
(21) Chung, K.; Waymouth, R. M. Selective Catalytic Oxidation of Unprotected
Carbohydrates. ACS Catal. 2016, 6, 4653-4659.
(22) Jeanloz, R. W. The Synthesis of D-Allosamine Hydrochloride. J. Am. Chem. Soc.
1957, 79, 2591-2592.
(23) Jäger, V.; Schröter, D. Synthesis of Amino Sugars via Isoxazolines: D-Allosamine.
Synthesis 1990, 556-560.
(24) Wong, C. H.; Ichikawa, Y.; Krach, T.; Gautheron-Le Narvor, C.; Dumas, D. P.; Look,
G. C. Probing the acceptor specificity of -1,4-galactosyltransferase for the
development of enzymatic synthesis of novel oligosaccharides. J. Am. Chem. Soc.
1991, 113, 8137-8145.
ACS Paragon Plus Environment
29