Reaction:JCGG-RAC0002182

JCGG ID

JCGG-RAC0002182

Submitter

The Noguchi Institute

Reaction ID

R-0000-002182

Regist Date

2012/06/21 18:45:10

REACTANT

MOLECULE ID

JCGG-COM0002807 (Reaction Tree)

Mol

0.22 mmol

MOLECULE ID

JCGG-COM0002622

Reactant Type

NCS

Mol

0.44 mmol

PRODUCT

MOLECULE ID

JCGG-COM0002823 (Reaction Tree)

Skeleton

JCGG-STR032525

Product Type

alpha

Yield

91%(alpha/beta=1.3/1)

MOLECULE ID

JCGG-COM0002824 (Reaction Tree)

Skeleton

JCGG-STR031569

Product Type

beta

Yield

91%(alpha/beta=1.3/1)

REACTION DETAIL

Reaction Time

1 hour

Reaction Temp

50 degree C

Solvent

THF/H2O = 9/1

COMMENT

Keywords: N,O-dimethyloxyamine-N-glycosides, protecting group manipulations, N-chlorosuccinimide, NCS, thioglycoside, trichloroacetimidate, complex oligosaccharide synthesis

REFERENCE

Reference Id

REF-0000-000323

Issn

Electronic

Doi

10.1021/jo102372m

PubMed ID

21332162

Journal Name

The Journal of organic chemistry. (2011) 76 (6): 1918-21.

Article Title

Use of N,O-dimethylhydroxylamine as an anomeric protecting group in carbohydrate synthesis.

Author

Somnath, Dasgupta; Mark, Nitz

Affiliation

Department of Chemistry, University of Toronto, 80 St. George St., Toronto, ON, Canada M5S 3H6.

Reference Id

REF-0000-000324

Source

J. Org. Chem. 2011, 76, 1918-1921

Doi

10.1021/jo102372m