JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
 JCGG-RAC0002073
Submitter
 The Noguchi Institute
Reaction ID
 R-0000-002073
Regist Date
 2012/06/21 18:31:41
REACTANT
MOLECULE ID
 JCGG-COM0002679 (Reaction Tree)
Skeleton
JCGG-STR032525
Mol
 0.45 mmol
MOLECULE ID
 JCGG-COM0002709 (Reaction Tree)
Mol
 0.37 mmol
MOLECULE ID
 JCGG-COM0000746
Reactant Type
 1H-tetrazole
Mol
 0.90 mmol
MOLECULE ID
 JCGG-COM0001275
Reactant Type
 BH3*THF (1 M in THF)
Mol
 1.87 mmol
PRODUCT
MOLECULE ID
 JCGG-COM0002710 (Reaction Tree)
Yield
 84%
REACTION DETAIL
Reaction Time
 25 minutes, 15 minutes
Reaction Temp
 room temp, room temp
Solvent
 dry MeCN, dry THF
Comment
 1) +all except BH3*THF, 2) +BH3*THF
COMMENT
Keywords: alpha-D-glycosyl boranophosphate, phosphoramidite, condensation, boronation, terminal deprotection, Leishmania glycocalyx lipophosphoglycans
There are multiple phases in this reaction.
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)