JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0001100
Submitter
The Noguchi Institute
Reaction ID
R-0000-001054
Regist Date
2012/06/21 16:36:47
REACTANT
MOLECULE ID
JCGG-COM0001166 (Reaction Tree)
Reactant Type
6-O-TIPS-3,4-cyclocarbonate galactal
Mol
5.94 mmol
MOLECULE ID
JCGG-COM0000753
Reactant Type
DMDO (ca. 0.07 M)
Volume
90 mL
MOLECULE ID
JCGG-COM0001167 (Reaction Tree)
Mol
2.76 mmol
MOLECULE ID
JCGG-COM0000754
Reactant Type
ZnCl2 (1 M in THF)
Mol
6.00 mmol
PRODUCT
MOLECULE ID
JCGG-COM0001168 (Reaction Tree)
Yield
76%
REACTION DETAIL
Reaction Time
30 minutes, 2.5 hours
Reaction Temp
0 degree C, room temp
Solvent
CH2Cl2, THF
Comment
1) 17+DMDO, 2) +all the rest
The reactants were mixed at 0 degree in Celsius, and allowed to raise to room temperature. (second phase)
COMMENT
There are two 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)