Synthesis of Dysibetaine

Structure of Dysibetaine

C9H16N2O4

Principal investigator	Yoshihisa Kobayashi
Publication year	2009
Synthesis type	Total
Number of steps	11 (linear)
References	Angew. Chem. Int. Ed. 2009, 48, 1845.

Part 1 of 1

intermediate structure

Cl3CCH(OH)2

intermediate structure

SOCl2

Reflux, 60 h

intermediate structure

HCl, CH2N2

Et2O

RT, 60 min, 97% (3 steps)

See the Nierenstein reaction

intermediate structure

NaI, NaN3

MeCN

RT, 90 min, 99%

intermediate structure

+

intermediate structure

TMS2NH

HFIPA

RT, ON, 85%

See the Ugi Reaction

intermediate structure

Pyr, Ac2O

CH2Cl2

RT, 24 h, 92%

intermediate structure

Camphorsulfonic acid

PhH

60 °C, 90 min, 29%

"Also isolated was the C5-epimer (50 % yield)."

intermediate structure

NaOH

H2O, MeOH

RT, 36 h, 100%

intermediate structure

Pd/C, HCl, H2, CH2O

1 atm

H2O, MeOH

RT, 18 h, 99%

intermediate structure

MeI

THF

RT, 24 h, 84%

intermediate structure

Dowex 550A

MeOH

100%

intermediate structure

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