Chemistry Reference
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OH
HO
O
ClOP(OR)
2
Toluene / Py
10a
-
h
CHO
OH
O
O
H
HO
H
H
OH
HO
CH
2
OH
O
ClOP(OR)
2
Toluene / Py
11a
-
h
D-xylose
O
OH
O
HO
O
ClOP(OR)
2
Toluene / Py
12a
-
h
HO
O
O
HO
HO
O
O
OH
O
AcO
O
ClOP(OR)
2
Toluene / Py
CHO
OH
14a
-
h
H
O
O
HO
HO
H
H
OH
H
OH
R
CH
2
OH
OH
HO
O
13a
-
h
and
16a
-
h
ClOP(OR)
2
Toluene / Py
D-glucose
HO
O
OAc
O
HO
O
O
O
OH
O
ClOP(OR)
2
Toluene / Py
OH
15a
-
h
O
O
Scheme 10.7
Synthesis of furanoside
diphosphite ligands
10-16:
(i) I
2
/acetone
(95% yield); (ii) H
2
SO
4
/CH
3
OH (90% yield);
(iii) BzCl/CH
2
Cl
2
/Py,
−
20 °C to room temp.
(85% yield); (iv) PCC/AcONa/CH
2
Cl
2
then
NaBH
4
/EtOH/H
2
O,
−
15 °C (70% yield); (v)
NH
4
OH/MeOH (70% yield); (vi) I
2
/acetone
(98% yield); (vii) PCC/AcONa/CH
2
Cl
2
then
NaBH
4
/EtOH/H
2
O,
−
15 °C (82% yield); (viii)
Ac
2
O/Py/CH
2
Cl
2
, 0 °C to room temp. (91%
yield); (ix) AcOH/H
2
O (88% yield); (x) TsCl/
Py/CH
2
Cl
2
,
−
20 °C to room temp. (88%); (xi)
NaOMe/CH
2
Cl
2
then LiAlH
4
/THF, 60 °C (92%
yield); (xii) Ac
2
O/Py/CH
2
Cl
2
, 0 °C to room
temp. (90% yield); (xiii) Tf
2
O/Py/CH
2
Cl
2
(57% yield); (xiv) NaOMe/CH
2
Cl
2
then
LiAlH
4
/THF, 60 °C (79% yield); (xv) Ac
2
O/Py/
CH
2
Cl
2
, 0 °C to room temp. (87% yield); (xvi)
AcOH/H
2
O (84% yield); (xvii) TsCl/Py/
CH
2
Cl
2
,
−
20 °C to room temp. (81%); (xviii)
NaOMe/CH
2
Cl
2
then LiAlH
4
/THF, 60 °C (92%
yield); (xix) Ac
2
O/Py/CH
2
Cl
2
, 0 °C to room
temp. (92% yield); (xx) Tf
2
O/Py/CH
2
Cl
2
(54%
yield); (xxi) NaOMe/CH
2
Cl
2
then LiAlH
4
/THF,
60 °C (78% yield).
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