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OAc
O
Ac AcO
S
O
AcO
AcO
AcO
O
Ac AcO
AcO
OMe
AcO
OMe
4
6
OAc
89%, dr >99 : 1
O
AcO
AcO
h
ν
( 365 nm)
DPAP
SH
AcO
OAc
1
O
Ac AcO
(1.3 eq.)
S
OMe
OMe
O
O
AcO
O
O
O
O
7
5
92%, dr >99 : 1
SCHEME 3.3
Synthesis of exact S -disaccharide isosteres via TEC.
O
OAc
OAc
OAc
O
O
O
O
O
AcO
AcO
Ac AcO
AcO
AcO
O
S
S
S
OMe
O
O
AcO
AcO
AcO
O
AcO
AcO
8 (64%)
AcO
OMe
OO
6 (89%)
7 (92%)
OAc
OAc
OAc
O
O A c
O A c
O A c
O
O
O
O
O
AcO
AcO
Ac AcO
Ac AcO
O
S
O
O
O
O
S
S
O
10 (80%)
O
O
AcO
AcO
9 (76%)
AcO
OMe
11 (89%)
O
OAc
OAc
O
OAc
O
O A c
O
O
O
AcO
AcO
AcO
AcO
AcO
AcO
O
S
S
S
O
AcHN
AcHN
O
AcO
AcO
O
AcO
AcO
AcO
13 (55%)
AcO
OMe
OMe
12 (82%)
14 (79%)
FIGURE 3.3
Collection of S -disaccharides prepared via TEC.
 
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