Paper
Green Chemistry
polarimeter using a quartz cell with 3 mL capacity and a 1 dm
path length. Concentrations (c) are given in g per 100 ml. High
resolution mass spectra were recorded on a Bruker micrOTOF
II spectrometer using electrospray ionization. Commercially
available grades of organic solvents of adequate purity were
used in all reactions.
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Gram-scale synthesis of 2b and recycle of DTT
To a 0.15 M solution of 1b (2.0 g, 4.92 mmol, 1.0 equiv.) and
V (1.14 g, 7.38 mmol, 1.5 equiv.) in DMA was added NaHCO3
(41 mg, 0.492 mmol, 0.1 equiv.). The mixture was stirred at
room temperature for 1 h and then poured into water and
extracted with toluene three times. The combined organic
layers were washed successively with water and brine and con-
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concentrated. The residue was dissolved in MeOH (contains
0.1‰ (w/w) K2CO3) and stirred at room temperature for
30 min. Then the mixture was filtered with Celite and washed
with MeOH. The filtrate was concentrated to give V (1.05 g,
recovered yield 92%). The recycled DTT was further utilized in
the next selective S-deacetylation reaction and produced 2b in
94% yield.
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Acknowledgements
We thank the National Natural Science Foundation of China
(21272082, 21402055, 21472054), the Specialized Research
Fund for the Doctoral Program of Higher Education
(20120142120092), the Recruitment Program of Global Youth
Experts of China, the State Key Laboratory of Bio-organic and
Natural Products Chemistry (SKLBNPC13425), and Huazhong
University of Science and Technology (2014ZZGH015) for
support.
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2550 | Green Chem., 2015, 17, 2545–2551
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