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Named reactions

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Search synthesis

Pactamycin

Chemical structure of Pactamycin
C28H38N4O8
Author Stephen Hanessian
Publication year 2011
Synthesis type Total synthesis
Number of steps 35 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
BnOH, TsOH
PhH
Reflux, 24 h, 67%

See the Fischer Esterification
Chemical structure
p-MeOBzCl, Et3N
CH2Cl2
RT, 2 h, 64%
Chemical structure
SOCl2
MeCN
0 °C to RT, 10 h, 85%
Chemical structure + Chemical structure
TMS2NLi
THF
-78 °C, 55 min

See the Aldol Addition
Chemical structure
TESOTf, 2,6-Lutidine
CH2Cl2
0 °C to RT, 2 h, 67% (2 steps)
Chemical structure
i-Bu2AlH
CH2Cl2
-78 °C
Chemical structure
MeMgBr
Et2O
0 °C, 60 min, 87% (2 steps)

See the Grignard Reaction
Chemical structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 to 0 °C, 105 min, 91%

See the Swern Oxidation
Chemical structure
  1. O3
  2. Me2S
CH2Cl2
-78 °C to RT, ON, 84%
Chemical structure
TiCl4, i-Pr2NEt, TMSCl
CH2Cl2
0 °C, 20 min, 85%

See the Aldol Addition
Chemical structure
Cl3CCOCl, Pyr
CH2Cl2
RT, 8 h, 89%
Chemical structure
H2O2, NaOH
CH2Cl2, MeOH, H2O
0 °C, 2 h, 75%

See the Michael Addition
Also isolated was the TES-deprotected product (16 % yield).
Chemical structure
NaBH4, CeCl3.7H2O
MeOH, CH2Cl2
0 °C, 70 min, 92%

See the Luche Reduction
Chemical structure
Tf2O, Pyr
CH2Cl2
-78 to 0 °C, 60 min
Chemical structure
n-Bu4N+ N3-
4 Å MS
PhMe
RT, 3 d, 86% (2 steps)
Chemical structure
CF3CO2H
MeCN, H2O
0 °C, 4 h, 93%
Chemical structure
Dess-Martin Periodinane
CH2Cl2
0 °C to RT, 2 h, 96%

See the Dess-Martin Oxidation
Chemical structure
MeMgBr
THF
-78 °C, 3 h, 91%

See the Grignard Reaction
Chemical structure
n-Bu4N+ F-
THF
0 °C to RT, 90 min, 95%
Chemical structure
Zn(OTf)2
AcOH
80 °C, 2 d

See the Payne Rearrangement
Chemical structure
K2CO3
MeOH
0 °C to RT, 60 min, 87% (2 steps)
Chemical structure
TBDPSCl, Et3N, DMAP
CH2Cl2
0 °C to RT, 4 h, 96%
Chemical structure
Tf2O, Pyr
CH2Cl2
-78 to 0 °C, 60 min, 96%
Chemical structure + Chemical structure
Yb(OTf)3
PhMe
80 °C, 9 h, 81%

The yield was 91 % brsm.
Chemical structure
HCl
THF, H2O
0 °C to RT, 14 h, 63%

The yield was 83 % after two cycles.
Chemical structure
TASF
CH2Cl2
0 °C to RT, 60 min, 95%
Chemical structure
2,2-Dimethoxypropane, Camphorsulfonic acid
CH2Cl2
0 °C to RT, 2 h, 86%
Chemical structure
ClCO2CCl3, Et3N
Activated charcoal
THF
-46 °C, 15 min, 89%
Chemical structure
Me2NH
-46 °C to RT, 97%
Chemical structure
i-Bu2AlH
CH2Cl2
-78 °C, 90 min, 90%
Chemical structure
OsO4, NMO
THF, Acetone, H2O
0 °C to RT, 2 h

See the Upjohn Dihydroxylation
Chemical structure
NaIO4
THF, H2O
RT, 3 h, 80% (2 steps)
Chemical structure
CF3CO2H
MeCN, H2O
0 °C to RT, 45 min, 85%
Chemical structure + Chemical structure
K2CO3
DMA
RT, 70 min, 96%
Chemical structure
H2, Lindlar Catalyst
1 atm
MeOH, EtOH
RT, 3 h, 85%
Chemical structure

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