Reaction:JCGG-RAC0002313

JCGG ID		JCGG-RAC0002313
Submitter		The Noguchi Institute
Reaction ID		R-0000-002313
Regist Date		2012/06/21 19:01:30
REACTANT
MOLECULE ID		JCGG-COM0003017 (Reaction Tree)
	Reactant Type	(in Ac2O)
	Mol	1.66 mmol
MOLECULE ID		JCGG-COM0001374
	Reactant Type	HNO3 (70% w/w)
	Mol	6.32 mmol
MOLECULE ID		JCGG-COM0000047
	Reactant Type	TEA
	Mol	1.99 mmol
PRODUCT
MOLECULE ID		JCGG-COM0003018 (Reaction Tree)
	Yield	77%
REACTION DETAIL
Reaction Time		1.5 hours, 2 hours
Reaction Temp		-33 degree C, room temp
Solvent		Ac2O, CH2Cl2
Comment		1) +all except TEA, 2) +TEA
		Before the reaction, HNO3 was added dropwise to Ac2O at 10 degree in Celsius. (internal temperature was kept in the range of 20 to 25 degree)
		7 was added slowly.
		The reactants were mixed at 0 degree in Celsius before stirred at room temperature. (second phase)
COMMENT
Keywords: 2-acylamino uronic acid, glycosyl phosphonates, oxidation, uronate 2-nitro-glycal, thermodynamic 1,2-trans-di-equatorial phosphonylation
There are multiple phases in this reaction.
REFERENCE
Reference Id		REF-0000-000331
	Issn	Electronic
	Doi	10.1021/jo2002193
	PubMed ID	21495699
	Journal Name	The Journal of organic chemistry. (2011) 76 (10): 4099-104.
	Article Title	Accessing C-1 phosphonylated 2-acylamino uronic acids via 2-nitro-glycals.
	Author	Beenu, Bhatt; Robin J, Thomson; Mark, von Itzstein
	Affiliation	Institute for Glycomics, Griffith University, Gold Coast Campus, Queensland 4222, Australia.
Reference Id		REF-0000-000332
	Source	J. Org. Chem. 2011, 76, 4099-4104
	Doi	10.1021/jo2002193