JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
 JCGG-RAC0001090
Submitter
 The Noguchi Institute
Reaction ID
 R-0000-001097
Regist Date
 2012/06/21 16:38:59
REACTANT
MOLECULE ID
 JCGG-COM0001228 (Reaction Tree)
Mol
 0.0160 mmol
MOLECULE ID
 JCGG-COM0001179 (Reaction Tree)
Mol
 0.0820 mmol
MOLECULE ID
 JCGG-COM0001173
Reactant Type
 di-tert-butylpyridine
Mol
 0.16 mmol
MOLECULE ID
 JCGG-COM0000008
Reactant Type
 Sn(OTf)2 (in 0.28 mL of THF)
Mol
 0.0576 mmol
PRODUCT
MOLECULE ID
 JCGG-COM0001229 (Reaction Tree)
Yield
 76%
REACTION DETAIL
Reaction Time
 15 minutes, 12 hours, 24 hours, 5 hours
Reaction Temp
 room temp, -7 degree C, 0 degree C, room temp
Solvent
 PhCH3, PhCH3/THF, PhCH3/THF, PhCH3/THF
Comment
 1) 71+23, di-tert-butylpyridine, 2) +Sn(OTf)2, 3) temperature change, 4) temperature change
MS 4A was included in the solvent.
The reactants were mixed at -15 degree in Celsius before stirred at -7 degree. (second phase)
COMMENT
There are four phases in this reaction.
REFERENCE
Reference Id
 REF-0000-000048
Issn
 Print
PubMed ID
 11273599
Journal Name
 Journal of the American Chemical Society. (2001) 123 (1): 35-48.
Article Title
 Total syntheses of tumor-related antigens N3: probing the feasibility limits of the glycal assembly method.
Author
 H M, Kim; I J, Kim; S J, Danishefsky
Affiliation
 Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Ave., New York, New York 10021, USA.
Reference Id
 REF-0000-000049
Source
 J. Am. Chem. Soc. 2001, 123, 35-48
Doi
 10.1021/ja0022730
©2008-2013 Research Center for Medical Glycoscience, National Institute of Advanced Industrial Science and Technology (AIST)