Reaction:JCGG-RAC0001069

JCGG ID		JCGG-RAC0001069
Submitter		The Noguchi Institute
Reaction ID		R-0000-001076
Regist Date		2012/06/21 16:37:55
REACTANT
MOLECULE ID		JCGG-COM0001196 (Reaction Tree)
	Reactant Type	azeotropically dried thioglycoside
	Mol	0.241 mmol
MOLECULE ID		JCGG-COM0001194 (Reaction Tree)
	Reactant Type	lactal
	Mol	0.135 mmol
MOLECULE ID		JCGG-COM0001173
	Reactant Type	di-tert-butylpyridine
	Mol	0.484 mmol
MOLECULE ID		JCGG-COM0000741
	Reactant Type	MeOTf
	Mol	0.963 mmol
PRODUCT
MOLECULE ID		JCGG-COM0001197 (Reaction Tree)
	Yield	70%
REACTION DETAIL
Reaction Time		10 minutes, 6 hours
Reaction Temp		room temp, -40 degree C to room temp
Solvent		CH2Cl2/Et2O = 3mL/6mL, CH2Cl2/Et2O = 3mL/6mL
Comment		1) 47+43, MS 4A, di-tert-butylpyridine, 2) +MeOTf
		MS 4A was included in the solvent.
		The reactants were mixed at -40 degree in Celsius, and allowed to warm to room temperature slowly within the reaction time. (second phase)
COMMENT
ATTENTION: There are numerical discrepancies between the scheme and the written method. (the number of % yield)
There might be a typo in Supporting Info. (1,4-di-tert-butylpyridine should be 2,6-di-tert-butylpyridine)
There are two phases in this reaction.
REFERENCE
Reference Id		REF-0000-000048
	Issn	Print
	PubMed ID	11273599
	Journal Name	Journal of the American Chemical Society. (2001) 123 (1): 35-48.
	Article Title	Total syntheses of tumor-related antigens N3: probing the feasibility limits of the glycal assembly method.
	Author	H M, Kim; I J, Kim; S J, Danishefsky
	Affiliation	Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Ave., New York, New York 10021, USA.
Reference Id		REF-0000-000049
	Source	J. Am. Chem. Soc. 2001, 123, 35-48
	Doi	10.1021/ja0022730