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OAc
OH
OAc
ab
O
O
O
AcO
AcO
HO
HO
Ac
AcO
S
OH
OH
OAc
Br
OAc
2
b
O
OAc
OAc
O
O
AcO
AcO
O
Ac
AcO
S
S
OAc
95%
OAc
a = i. (CH
3
CO)
2
O, HClO
4
, ii. 30% HBr in acetic acid; b = MoS
4
2-
, CH
3
CN
FIGURE 1.7
Thio-glucoside forming tandem sulfur transfer/reduction/Michael addition
assisted by tetrathiomolybdate [23].
excellent diastereoselectivity (but sometimes the ratio of diastereoisomers was 1:1).
The process is simple, offers good to excellent yields, and is performed in one pot.
While the authors did not consider the process to belong to click chemistry, it def-
initely shows most features of the click chemistry. Figures 1.7 and 1.8 illustrate the
methodology.
OH
[PhCH
2
S]
2
O
HO
O
AcO
AcO
Ph
S
AcO
AcO
O
AcO
AcO
OAc
S
OMe
O
O
2
AcO
a
O
OMe
O
AcO
AcO
O
OMe
a=MoS
4
2-
,CH
3
CN
S
MeOOC
AcO
S
NHBoc
OAc
2
MeOOC
O
NHBoc
O
FIGURE 1.8
Synthesis of 3-deoxy-3-thiosugar derivatives via Michael addition according
to Reference 23.
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