JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
 JCGG-RAC0002052
Submitter
 The Noguchi Institute
Reaction ID
 R-0000-002052
Regist Date
 2012/06/21 18:28:50
REACTANT
MOLECULE ID
 JCGG-COM0002662 (Reaction Tree)
Reactant Type
 intermediate
Mol
 3.078 to 3.8 mmol
MOLECULE ID
 JCGG-COM0002678
Reactant Type
 N,N-diisopropylphosphonamidate
Mol
 38.8 mmol
MOLECULE ID
 JCGG-COM0000426
Reactant Type
 DIEA
Mol
 9.5 mmol
PRODUCT
MOLECULE ID
 JCGG-COM0002679 (Reaction Tree)
Skeleton
JCGG-STR032525
Product Type
 alpha
Yield
 81%(at least, alpha/beta=98/2)
MOLECULE ID
 JCGG-COM0002680 (Reaction Tree)
Skeleton
JCGG-STR031569
Product Type
 beta
Yield
 81%(at least, alpha/beta=98/2)
REACTION DETAIL
Reaction Time
 1 day
Reaction Temp
 room temp
Solvent
 dry PhCH3
COMMENT
Keywords: alpha-D-glycosyl boranophosphate, phosphoramidite, condensation, boronation, terminal deprotection, Leishmania glycocalyx lipophosphoglycans
REFERENCE
Reference Id
 REF-0000-000315
Issn
 Electronic
Doi
 10.1021/jo102584g
PubMed ID
 21381786
Journal Name
 The Journal of organic chemistry. (2011) 76 (8): 2648-59.
Article Title
 Synthesis of oligo(α-D-glycosyl phosphate) derivatives by a phosphoramidite method via boranophosphate intermediates.
Author
 Shoichi, Fujita; Natsuhisa, Oka; Fumiko, Matsumura; Takeshi, Wada
Affiliation
 Department of Medical Genome Sciences, Graduate School of Frontier Sciences, The University of Tokyo, Bioscience Building 702, 5-1-5 Kashiwanoha, Kashiwa, Chiba 277-8562, Japan.
Reference Id
 REF-0000-000316
Source
 J. Org. Chem. 2011, 76, 2648-2659
Doi
 10.1021/jo102584g
©2008-2013 Research Center for Medical Glycoscience, National Institute of Advanced Industrial Science and Technology (AIST)