Reaction:JCGG-RAC0002716

JCGG ID		JCGG-RAC0002716
Submitter		The Noguchi Institute
Reaction ID		R-0000-002716
Regist Date		2012/06/21 19:41:58
REACTANT
MOLECULE ID		JCGG-COM0003495 (Reaction Tree)
	Reactant Type	donor
	Mol	1 equiv.
MOLECULE ID		JCGG-COM0003542 (Reaction Tree)
	Reactant Type	acceptor
	Mol	0.67 equiv.
MOLECULE ID		JCGG-COM0003517
	Reactant Type	Ph2SO
	Mol	1.1 equiv.
MOLECULE ID		JCGG-COM0002536
	Reactant Type	TTBP
	Mol	1.5 + 1.0 equiv.
MOLECULE ID		JCGG-COM0000761
	Reactant Type	Tf2O
	Mol	1.1 equiv.
PRODUCT
MOLECULE ID		JCGG-COM0003543 (Reaction Tree)
	Product Type	alpha
	Yield	78%(alpha/beta=5/4)
MOLECULE ID		JCGG-COM0003544 (Reaction Tree)
	Product Type	beta
	Yield	78%(alpha/beta=5/4)
REACTION DETAIL
Reaction Time		30 minutes, NOT specified
Reaction Temp		NOT specified, -60 degree C
Solvent		CH2Cl2, CH2Cl2
Comment		1) donor+Ph2SO, TTBP, MS 3A, 2) +Tf2O, acceptor, TTBP
		MS 3A was included in the solvent.
		The addition of Tf2O was performed before the addition of all the other reactants. (second phase)
		Tf2O was added at -45 degree in Celsius, while all the other reactants were added at -60 degree. (second phase)
COMMENT
Keywords: Streptococcus pneumonia, SP1, zwitterionic polysaccharide, ZPs, cis-glycosidic bond
There are multiple phases in this reaction.
REFERENCE
Reference Id		REF-0000-000363
	Issn	Electronic
	Doi	10.1021/jo102363d
	PubMed ID	21341806
	Journal Name	The Journal of organic chemistry. (2011) 76 (6): 1692-706.
	Article Title	Galacturonic acid lactones in the synthesis of all trisaccharide repeating units of the zwitterionic polysaccharide Sp1.
	Author	Alphert E, Christina; Leendert J, van den Bos; Herman S, Overkleeft; Gijsbert A, van der Marel; Jeroen D C, Codée
	Affiliation	Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
Reference Id		REF-0000-000364
	Source	J. Org. Chem. 2011, 76, 1692-1706
	Doi	10.1021/jo102363d