JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0001377
Submitter
The Noguchi Institute
Reaction ID
R-0000-001377
Regist Date
2012/06/21 16:55:54
REACTANT
MOLECULE ID
JCGG-COM0001572 (Reaction Tree)
Skeleton
JCGG-STR001961
Reactant Type
id=14 (in 4 mL of THF)
Mol
0.395 mmol
MOLECULE ID
JCGG-COM0001581
Reactant Type
TMS2NK (0.5 M in PhCH3)
Volume
1.90 mL
MOLECULE ID
JCGG-COM0001582
Reactant Type
HS(CH2)nSH
Mol
3 equiv. (approximately)
MOLECULE ID
JCGG-COM0001583
Reactant Type
HMPA
Volume
4 mL
MOLECULE ID
JCGG-COM0000086
Reactant Type
Ac2O
Volume
1 mL
MOLECULE ID
JCGG-COM0000979
Reactant Type
pyridine
Volume
2 mL
PRODUCT
MOLECULE ID
JCGG-COM0001595 (Reaction Tree)
Yield
78%
MOLECULE ID
JCGG-COM0001596 (Reaction Tree)
Yield
15%
REACTION DETAIL
Reaction Time
NOT specified, 30 minutes, 2 hours, 12 hours
Reaction Temp
-78 degree C, -78 degree C, ambient temperature, ambient temperature
Solvent
THF, THF, THF, THF
Comment
1) +TMS2NK, and degassed, 2) +HS(CH2)nSH, HMPA, and degassed, 3) +14, and degassed, 4) +Ac2O, pyridine
The reactants were mixed at -78 degree in Celsius, and gradually allowed to warm to ambient temperature. (third phase, after being degassed)
COMMENT
Keywords: Bisubstrate-type sialyltransferase inhibitors, CMP-NeuAc, N-acetyllactosamine, lactose, sialic acid, ST6N, ST3N
There are multiple phases in this reaction.
REFERENCE
Reference Id
REF-0000-000071
Issn
Print
Doi
10.1021/jo030042g
PubMed ID
12839452
Journal Name
The Journal of organic chemistry. (2003) 68 (14): 5602-13.
Article Title
Systematic syntheses and inhibitory activities of bisubstrate-type inhibitors of sialyltransferases.
Author
Hiroshi, Hinou; Xue-Long, Sun; Yukishige, Ito
Affiliation
RIKEN (The Institute of Physical and Chemical Research), 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan.
Reference Id
REF-0000-000072
Source
J. Org. Chem. 2003, 68, 5602-5613
Doi
10.1021/jo030042g

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