Reaction:JCGG-RAC0001295

JCGG ID		JCGG-RAC0001295
Submitter		The Noguchi Institute
Reaction ID		R-0000-001295
Regist Date		2012/06/21 16:49:22
REACTANT
MOLECULE ID		JCGG-COM0001455 (Reaction Tree)
	Reactant Type	acetal
	Mol	1 equiv.
MOLECULE ID		JCGG-COM0001346
	Reactant Type	DTBMP
	Mol	4 equiv.
MOLECULE ID		JCGG-COM0000741
	Reactant Type	MeOTf
	Mol	3.5 equiv.
MOLECULE ID		JCGG-COM0000110
	Reactant Type	TFA
	Volume	200 micro L
MOLECULE ID		JCGG-COM0000979
	Reactant Type	pyridine
	Volume	5.0 mL
MOLECULE ID		JCGG-COM0000086
	Reactant Type	Ac2O
	Volume	500 micro L
MOLECULE ID		JCGG-COM0000500
	Reactant Type	DMAP
	Mol	catalytic amount
PRODUCT
MOLECULE ID		JCGG-COM0001458 (Reaction Tree)
	Product Type	beta
	Yield	56%(beta only)
REACTION DETAIL
Reaction Time		NOT specified, 3 hours, 12 hours
Reaction Temp		50 degree C, 0 degree C, room temp
Solvent		(CH2Cl)2, CH2Cl2, CH2Cl2
Comment		1) acetal+DTBMP, MS 4A, MeOTf, 2) +TFA, 3) +all the rest
		MS 4A was included in the solvent.
		The reactants were mixed at room temperature before stirred at 50 degree in Celsius. (first phase)
COMMENT
Keywords: beta-L-rhamnopyranosides, stereoselective synthesis, beta-D-mannopyranosides, intramolecular aglycon delivery, IAD
There are multiple phases in this reaction.
The alpha/beta ratio was determined by 1H NMR after isolation.
REFERENCE
Reference Id		REF-0000-000065
	Issn	Electronic
	Doi	10.1021/ja801574q
	PubMed ID	18433121
	Journal Name	Journal of the American Chemical Society. (2008) 130 (20): 6330-1.
	Article Title	Stereoselective synthesis of beta-L-rhamnopyranosides.
	Author	Yong Joo, Lee; Akihiro, Ishiwata; Yukishige, Ito
	Affiliation	RIKEN (The Institute of Physical and Chemical Research), 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
Reference Id		REF-0000-000066
	Source	J. AM. CHEM. SOC. 2008, 130, 6330-6331
	Doi	10.1021/ja801574q