[zuriel]

Hi everyone,

I'm following an experimental procedure from this paper:

http://mend.endojournals.org/content/23/5/640.long

for compound X (p. 645) and I have a question about the AMOUNT of hydrazine hydrate used. They use 16.7 g of 85% hydrazine hydrate and, for me with 4 g of starting material using 60% hydrazine hydrate, it works out as 34.5 g (34 mL approx.).
I'm concerned about using this much of it though. Does anyone know WHY so MUCH is used? Is it necessary?

[discodermolide]

Work out the quantities in number of moles of both SM and hydrazine hydrate.

[kriggy]

Its about 8 times excess of hydrazine if I´m not wrong. I guess its because you want to have as little as possible of unreduced reagent. It seems that it also deprotects those hydroxy groups but I´m not sure on that, I´ve never seen this protecting group