Reaction:JCGG-RAC0001082

JCGG ID		JCGG-RAC0001082
Submitter		The Noguchi Institute
Reaction ID		R-0000-001089
Regist Date		2012/06/21 16:38:35
REACTANT
MOLECULE ID		JCGG-COM0001217 (Reaction Tree)
	Reactant Type	6-benzylglucal
	Mol	11.1 mmol
MOLECULE ID		JCGG-COM0000500
	Reactant Type	DMAP
	Mol	catalytic amount
MOLECULE ID		JCGG-COM0000979
	Reactant Type	pyridine
	Mol	33.3 mmol
MOLECULE ID		JCGG-COM0001065
	Reactant Type	trimethylacetyl chloride
	Mol	16.6 mmol
MOLECULE ID		JCGG-COM0000047
	Reactant Type	Et3N
	Mol	30.5 mmol
MOLECULE ID		JCGG-COM0001218
	Reactant Type	TESOTf
	Mol	10.7 mmol
MOLECULE ID		JCGG-COM0000667
	Reactant Type	DIBAL-H (1 M in PhCH3)
	Volume	14.6 mL
MOLECULE ID		JCGG-COM0000531
	Reactant Type	H2O
	Volume	10 mL
PRODUCT
MOLECULE ID		JCGG-COM0001219 (Reaction Tree)
	Yield	48.38%(72%, 96%, 70%)
REACTION DETAIL
Reaction Time		24 hours, 2 hours, 1 hour, overnight
Reaction Temp		room temp, 0 degree C, -78 degree C, room temp
Solvent		CH2Cl2, CH2Cl2, CH2Cl2, CH2Cl2
Comment		1) 61+DMAP, pyridine, trimethylacetyl chloride, 2) +Et3N, TESOTf, 3) +DIBAL, 4) +H2O
		The reactants were mixed at 0 degree in Celsius before stirred at room temperature. (first phase)
COMMENT
There are four phases in this reaction.
ATTENTION: There are numerical discrepancies between the scheme and the written method. (the number of % yield)
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