JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0000852
Submitter
The Noguchi Institute
Reaction ID
R-0000-000852
Regist Date
2012/06/21 16:26:33
REACTANT
MOLECULE ID
JCGG-COM0000978
Reactant Type
cis-4-hydroxy-D-proline
Mol
3.8 mmol
MOLECULE ID
JCGG-COM0000660
Reactant Type
SOCl2
Mol
4.25 mmol
MOLECULE ID
JCGG-COM0000548 (Reaction Tree)
Reactant Type
CbzCl
Mol
4.2 mmol
MOLECULE ID
JCGG-COM0000426
Reactant Type
DIEA
Mol
9.2 mmol
MOLECULE ID
JCGG-COM0000531
Reactant Type
H2O
Volume
3 mL
PRODUCT
MOLECULE ID
JCGG-COM0000974 (Reaction Tree)
Product Type
N-Cbz-4-hydroxy-D-proline methyl ester
Yield
82%
REACTION DETAIL
Reaction Time
22 hours, 12 hours
Reaction Temp
reflux, room temp
Solvent
MeOH, MeOH/H2O
Comment
1) cis-4-hydroxy-D-proline+SOCl2, 2) +CbzCl, DIEA, H2O
The reactants were mixed at 0 degree in Celsius, and stirred for 1 hour before undergoing reflux. (first phase)
COMMENT
The PMID could not be found.
There are two phases in this reaction.
REFERENCE
Reference Id
REF-0000-000038
Source
J. Am. Chem. Soc. 1996, 118, 6826-6840
Doi
10.1021/ja952265x

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