Synthesis of sulfated brassinosteroids.
A number of water soluble sulfates of 24-epibrassinolide including the 2α,3α-disulfate and all possible monosulfates were synthesized. The target compounds were isolated in crystalline form as the corresponding sodium salts. Pyridine-sulfur trioxide complex was used as sulfating agent followed by transformation of the resulting pyridinium salts into the sodium sulfates by treatment with NaOH. The control of the regioselectivity was achieved by an appropriate use of acetyl and benzyl protecting groups.
Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich str. 5/2, 220141 Minsk, Belarus.
Halina A
HA
Zhylitskaya
Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich str. 5/2, 220141 Minsk, Belarus.
Natalia M
NM
Chashchina
Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich str. 5/2, 220141 Minsk, Belarus.
Raisa P
RP
Litvinovskaya
Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich str. 5/2, 220141 Minsk, Belarus.
Margarita I
MI
Zavadskaya
Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich str. 5/2, 220141 Minsk, Belarus. Electronic address: vz@iboch.bas-net.by.
Vladimir N
VN
Zhabinskii
Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich str. 5/2, 220141 Minsk, Belarus.
Vladimir A
VA
Khripach
D000085:Acetates / Q000737:chemistry; D060406:Brassinosteroids / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D013260:Steroids, Heterocyclic / Q000737:chemistry; D013431:Sulfates / Q000737:chemistry; D013461:Sulfur Oxides / Q000737:chemistry
D000085:Acetates; D060406:Brassinosteroids; D013260:Steroids, Heterocyclic; D013431:Sulfates; D013461:Sulfur Oxides; C012036:sodium sulfate; C011118:sulfur trioxide; C023623:brassinolide
Acetates; Benzyl ethers; Brassinosteroids; Epibrassinolide; Sulfation