JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0002069
Submitter
The Noguchi Institute
Reaction ID
R-0000-002069
Regist Date
2012/06/21 18:31:17
REACTANT
MOLECULE ID
JCGG-COM0002701 (Reaction Tree)
Mol
43 micro mole
MOLECULE ID
JCGG-COM0002702
Reactant Type
Me2NH (2 M in THF)
Mol
0.64 + 1.1 + 0.86 mmol
MOLECULE ID
JCGG-COM0002704
Reactant Type
AcONH4 (pH 4.6 buffer, solvent)
Volume
0.5 mL
PRODUCT
MOLECULE ID
JCGG-COM0002705 (Reaction Tree)
Yield
67%
REACTION DETAIL
Reaction Time
69 hours, 10 hours
Reaction Temp
room temp, room temp
Solvent
dry MeCN/dry THF, AcONH4 buffer
Comment
1) +all except AcONH4, 2) +AcONH4
Me2NH was added three times. (first phase; 0 hour, 6 hours, and 42 hours)
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)