JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
 JCGG-RAC0001342
Submitter
 The Noguchi Institute
Reaction ID
 R-0000-001343
Regist Date
 2012/06/21 16:51:50
REACTANT
MOLECULE ID
 JCGG-COM0001484 (Reaction Tree)
Reactant Type
 donor
Mol
 2.49 equiv.
MOLECULE ID
 JCGG-COM0001529 (Reaction Tree)
Skeleton
JCGG-STR032527
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-COM0001532 (Reaction Tree)
Product Type
 alpha
id=22+4h
Yield
 47%(alpha/beta=1/2.80)
MOLECULE ID
 JCGG-COM0001533 (Reaction Tree)
Product Type
 beta
id=22+4h
Yield
 47%(alpha/beta=1/2.80)
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)