Reaction:JCGG-RAC0002312

JCGG ID		JCGG-RAC0002312
Submitter		The Noguchi Institute
Reaction ID		R-0000-002312
Regist Date		2012/06/21 19:01:25
REACTANT
MOLECULE ID		JCGG-COM0003014 (Reaction Tree)
	Reactant Type	sugar (1,5-anhydro-3,4-di-O-benzyl-2-deoxy-D-arabino-hex-1-enuronate)
	Mol	3.06 mmol
MOLECULE ID		JCGG-COM0003015
	Reactant Type	DMP
	Mol	3.68 mmol
MOLECULE ID		JCGG-COM0000487
	Reactant Type	2-methyl-2-butene
	Mol	5.09 mmol
MOLECULE ID		JCGG-COM0003016
	Reactant Type	NaOCl2 (in H2O)
	Mol	6.79 mmol
MOLECULE ID		JCGG-COM0000486
	Reactant Type	NaH2PO4 (in H2O)
	Mol	5.09 mmol
MOLECULE ID		JCGG-COM0002179
	Reactant Type	KHCO3
	Mol	4.25 mmol
MOLECULE ID		JCGG-COM0001727
	Reactant Type	MeI
	Mol	4.18 mmol
PRODUCT
MOLECULE ID		JCGG-COM0003017 (Reaction Tree)
	Yield	77%
REACTION DETAIL
Reaction Time		2 hours, 2 hours, 3 hours
Reaction Temp		room temp, room temp, room temp
Solvent		anhydrous CH2Cl2, t-BuOH, anhydrous DMF
Comment		1) sugar+DMP, 2) +2-methyl-2-butene, NaOCl2, NaH2PO4, 3) +KHCO3, MeI
COMMENT
Keywords: 2-acylamino uronic acid, glycosyl phosphonates, oxidation, uronate 2-nitro-glycal, thermodynamic 1,2-trans-di-equatorial phosphonylation
There are multiple phases in this reaction.
ATTENTION: The chemical structure of NaOCl2 could not be found. (a plausible structure is being registered)
REFERENCE
Reference Id		REF-0000-000331
	Issn	Electronic
	Doi	10.1021/jo2002193
	PubMed ID	21495699
	Journal Name	The Journal of organic chemistry. (2011) 76 (10): 4099-104.
	Article Title	Accessing C-1 phosphonylated 2-acylamino uronic acids via 2-nitro-glycals.
	Author	Beenu, Bhatt; Robin J, Thomson; Mark, von Itzstein
	Affiliation	Institute for Glycomics, Griffith University, Gold Coast Campus, Queensland 4222, Australia.
Reference Id		REF-0000-000332
	Source	J. Org. Chem. 2011, 76, 4099-4104
	Doi	10.1021/jo2002193