JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0001335
Submitter
The Noguchi Institute
Reaction ID
R-0000-001336
Regist Date
2012/06/21 16:51:25
REACTANT
MOLECULE ID
JCGG-COM0001489 (Reaction Tree)
Reactant Type
donor
Mol
2.49 equiv.
MOLECULE ID
JCGG-COM0001492 (Reaction Tree)
Reactant Type
acceptor
Mol
1.0 equiv.
MOLECULE ID
JCGG-COM0000129
Reactant Type
NIS
Mol
3.74 equiv.
MOLECULE ID
JCGG-COM0000624
Reactant Type
AgOTf
Mol
0.39 equiv.
PRODUCT
MOLECULE ID
JCGG-COM0001519 (Reaction Tree)
Product Type
alpha
Yield
99%(alpha/beta=5.26/1)
MOLECULE ID
JCGG-COM0001520 (Reaction Tree)
Skeleton
JCGG-STR006602
Product Type
beta
Yield
99%(alpha/beta=5.26/1)
REACTION DETAIL
Reaction Time
3 hours
Reaction Temp
-40 degree C
Solvent
dry CH2Cl2
Comment
Freshly dried MS3A was included in the solvent.
The donor, the acceptor, and MS3A were mixed at room temperature before the reaction.
COMMENT
Keywords: stereoselective synthesis, mycobacterial arabinan, arabinofuranosyl donors, arabinofuranosylation, TIDPS
REFERENCE
Reference Id
REF-0000-000067
Issn
Print
Doi
10.1021/ol062198j
PubMed ID
17107063
Journal Name
Organic letters. (2006) 8 (24): 5525-8.
Article Title
Stereoselective synthesis of a fragment of mycobacterial arabinan.
Author
Akihiro, Ishiwata; Hiroko, Akao; Yukishige, Ito
Affiliation
RIKEN (Institute of Physical and Chemical Research), Wako-shi, Saitama 351-0198, Japan.
Reference Id
REF-0000-000068
Source
ORGANIC LETTERS, 2006, Vol. 8, No. 24, 5525-5528
Doi
10.1021/ol062198j

©2008-2013 Research Center for Medical Glycoscience, National Institute of Advanced Industrial Science and Technology (AIST)