Reaction:JCGG-RAC0002386

JCGG ID		JCGG-RAC0002386
Submitter		The Noguchi Institute
Reaction ID		R-0000-002386
Regist Date		2012/06/21 19:08:24
REACTANT
MOLECULE ID		JCGG-COM0003105 (Reaction Tree)
	Mol	1.56 mmol
MOLECULE ID		JCGG-COM0000761
	Reactant Type	Tf2O
	Mol	3.12 mmol
MOLECULE ID		JCGG-COM0000979
	Reactant Type	pyridine
	Mol	3.12 mmol
MOLECULE ID		JCGG-COM0000634
	Reactant Type	NaN3
	Mol	3.12 mmol
PRODUCT
MOLECULE ID		JCGG-COM0003107 (Reaction Tree)
	Yield	82%
REACTION DETAIL
Reaction Time		2 + 10 minutes, 1 hour
Reaction Temp		0 degree C, room temp
Solvent		CH2Cl2, DMF
Comment		1) +all except NaN3, 2) +NaN3
		Tf2O was added dropwise.
		Pyridine was added 2 minutes after the initiation of the reaction. (first phase)
COMMENT
Keywords: mannose, glucosamine, galactosamine, thioglycosides, 3-O-acylation, 4,6-O-benzylidenation, azide displacement, Lattrell-Dax inversion
There are multiple phases in this reaction.
REFERENCE
Reference Id		REF-0000-000337
	Issn	Electronic
	Doi	10.1021/jo200342v
	PubMed ID	21510706
	Journal Name	The Journal of organic chemistry. (2011) 76 (11): 4703-9.
	Article Title	Rapid transformation of D-mannose into orthogonally protected D-glucosamine and D-galactosamine thioglycosides.
	Author	Madhu, Emmadi; Suvarn S, Kulkarni
	Affiliation	Department of Chemistry, Indian Institute of Technology Bombay, Mumbai, India.
Reference Id		REF-0000-000338
	Source	J. Org. Chem. 2011, 76, 4703-4709
	Doi	10.1021/jo200342v