JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
 JCGG-RAC0001091
Submitter
 The Noguchi Institute
Reaction ID
 R-0000-001098
Regist Date
 2012/06/21 16:39:04
REACTANT
MOLECULE ID
 JCGG-COM0001229 (Reaction Tree)
Mol
 0.019 mmol
MOLECULE ID
 JCGG-COM0000160
Reactant Type
 Na (in 7 mL of liquid NH3)
Weight
 0.070g
MOLECULE ID
 JCGG-COM0000500
Reactant Type
 DMAP
Mol
 catalytic amount
MOLECULE ID
 JCGG-COM0000979
Reactant Type
 pyridine
Volume
 1 mL
MOLECULE ID
 JCGG-COM0000086
Reactant Type
 Ac2O
Volume
 0.5 mL
MOLECULE ID
 JCGG-COM0000753
Reactant Type
 DMDO (0.75 M solution)
Volume
 0.3 mL
MOLECULE ID
 JCGG-COM0000316
Reactant Type
 allyl alcohol (solvent)
Volume
 5 mL
MOLECULE ID
 JCGG-COM0000530
Reactant Type
 NaOMe
Mol
 NOT specified
PRODUCT
MOLECULE ID
 JCGG-COM0001230 (Reaction Tree)
Skeleton
JCGG-STR031375
Yield
 40%(total)
MOLECULE ID
 JCGG-COM0001231 (Reaction Tree)
Product Type
 mannose type isomer
Yield
 15%(total)
REACTION DETAIL
Reaction Time
 45 minutes, overnight, 15 minutes + 18 hours, 45 minutes, overnight, NOT specified
Reaction Temp
 -78 degree C, room temp, room temp, 0 degree C, room temp, NOT specified
Solvent
 anhydrous THF, MeOH, pyridine/Ac2O, CH2Cl2, CH2Cl2, MeOH
Comment
 1) Na+72, 2) +MeOH(solvent), 3) +Dowex 50-X8, DMAP, pyridine, Ac2O, 4) +DMDO, 5) +allyl alcohol, 6) +NaOMe
Dowex 50-X8 was included in the solvent.
The product of the second phase and Dowex 50-X8 were mixed and stirred for 15 minutes before the reaction. (third phase)
COMMENT
There are six phases in this reaction.
The procedure regarding the sixth phase is discussed in another paper in References.
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)