JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
 JCGG-RAC0001373
Submitter
 The Noguchi Institute
Reaction ID
 R-0000-001373
Regist Date
 2012/06/21 16:55:11
REACTANT
MOLECULE ID
 JCGG-COM0001580 (Reaction Tree)
Skeleton
JCGG-STR013782
Reactant Type
 id=13 (in 4 mL of THF)
Mol
 0.398 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
 1.19 mmol
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-COM0001584 (Reaction Tree)
Yield
 82%
MOLECULE ID
 JCGG-COM0001585 (Reaction Tree)
Yield
 12%
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) +13, 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)