Reaction:JCGG-RAC0002805

JCGG ID

JCGG-RAC0002805

Submitter

The Noguchi Institute

Reaction ID

R-0000-002805

Regist Date

2012/06/21 19:51:37

REACTANT

MOLECULE ID

JCGG-COM0003636 (Reaction Tree)

Reactant Type

donor

Mol

1 equiv.

MOLECULE ID

JCGG-COM0000071 (Reaction Tree)

Skeleton

JCGG-STR032525

Reactant Type

acceptor (0.3 to 0.5 M in CH2Cl2)

Mol

1.5 equiv.

MOLECULE ID

JCGG-COM0003517

Reactant Type

Ph2SO

Mol

1.3 equiv.

MOLECULE ID

JCGG-COM0002536

Reactant Type

TTBP

Mol

2.5 equiv.

MOLECULE ID

JCGG-COM0000761

Reactant Type

Tf2O

Mol

1.3 equiv.

PRODUCT

MOLECULE ID

JCGG-COM0003677 (Reaction Tree)

Product Type

alpha

Yield

49%(alpha/beta=1/3.5)

MOLECULE ID

JCGG-COM0003678 (Reaction Tree)

Product Type

beta

Yield

49%(alpha/beta=1/3.5)

REACTION DETAIL

Reaction Time

NOT specified

Reaction Temp

0 degree C

Solvent

CH2Cl2 (0.05M)

Comment

The donor, Ph2SO, TTBP, and molecular sieves (3 A) were mixed and stirred for 30 minutes at room temperature before the reaction.

MS 3A was included in the solvent.

All the reactants except the acceptor were mixed at -80 degree in Celsius.

Before the addition of the acceptor, the temperature was raised to -60 degree in Celsius in 20 minutes and cooled back to 80 degree.

COMMENT

Keywords: mannuronic acids, mannopyranosides, mannopyranosyl methyl uronate, all-cis-linked tetrasaccharide

REFERENCE

Reference Id

REF-0000-000367

Issn

Electronic

Doi

10.1021/jo201179p

PubMed ID

21793528

Journal Name

The Journal of organic chemistry. (2011) 76 (18): 7301-15.

Article Title

Stereoselective synthesis of 2,3-diamino-2,3-dideoxy-β-D-mannopyranosyl uronates.

Author

Marthe T C, Walvoort; Gert-Jan, Moggré; Gerrit, Lodder; Herman S, Overkleeft; Jeroen D C, Codée; Gijsbert A, van der Marel

Affiliation

Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands.

Reference Id

REF-0000-000368

Source

J. Org. Chem. 2011, 76, 7301-7315

Doi

10.1021/jo201179p