JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0001062
Submitter
The Noguchi Institute
Reaction ID
R-0000-001069
Regist Date
2012/06/21 16:37:34
REACTANT
MOLECULE ID
JCGG-COM0001189 (Reaction Tree)
MOLECULE ID
JCGG-COM0001022
Reactant Type
TBAF
MOLECULE ID
JCGG-COM0000086
Reactant Type
Ac2O
MOLECULE ID
JCGG-COM0000500
Reactant Type
DMAP
MOLECULE ID
JCGG-COM0000047
Reactant Type
Et3N
MOLECULE ID
JCGG-COM0000530
Reactant Type
NaOMe
MOLECULE ID
JCGG-COM0000160
Reactant Type
Na
MOLECULE ID
JCGG-COM0000756
Reactant Type
NH3
PRODUCT
MOLECULE ID
JCGG-COM0001190 (Reaction Tree)
Yield
43%
REACTION DETAIL
Solvent
THF, CH2Cl2, MeOH, MeOH, pyridine
Comment
1) 32+TBAF, 2) +Ac2O, DMAP, Et3N, 3) +NaOMe, 4) +Na, 5) +Ac2O, DMAP
Ac2O and DMAP are used twice.
Very few were described regarding this reaction.
COMMENT
There are five 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

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