Reaction:JCGG-RAC0002521

JCGG ID

JCGG-RAC0002521

Submitter

The Noguchi Institute

Reaction ID

R-0000-002521

Regist Date

2012/06/21 19:23:11

REACTANT

MOLECULE ID

JCGG-COM0003282 (Reaction Tree)

Skeleton

JCGG-STR032397

Mol

0.28 mmol

MOLECULE ID

JCGG-COM0000009

Reactant Type

TMSOTf

Mol

0.84 mmol

PRODUCT

MOLECULE ID

JCGG-COM0003284 (Reaction Tree)

Skeleton

JCGG-STR032527

Yield

4.5%

MOLECULE ID

JCGG-COM0003297 (Reaction Tree)

Skeleton

JCGG-STR033114

Yield

46%

MOLECULE ID

JCGG-COM0003298 (Reaction Tree)

Skeleton

JCGG-STR024801

Yield

21%

REACTION DETAIL

Reaction Time

5 minutes

Reaction Temp

-30 degree C

Solvent

dry CH2Cl2

COMMENT

Keywords: Methyl 1,2-Ortho Esters, 1alpha,1'beta-disaccharides, BF3*Et2O

ATTENTION: There are typos in the scheme. (compound 11 should be 6, rt should be -30 degree C)

REFERENCE

Reference Id

REF-0000-000349

Issn

Electronic

Doi

10.1021/jo202335n

PubMed ID

22141592

Journal Name

The Journal of organic chemistry. (2012) 77 (1): 795-800.

Article Title

Unexpected stereocontrolled access to 1α,1'β-disaccharides from methyl 1,2-ortho esters.

Author

Clara, Uriel; Juan, Ventura; Ana M, Gómez; J Cristóbal, López; Bert, Fraser-Reid

Affiliation

Instituto de Química Orgánica General (IQOG-CSIC), Juan de la Cierva 3, 28006 Madrid, Spain.

Reference Id

REF-0000-000350

Source

J. Org. Chem. 2012, 77, 795-800

Doi

10.1021/jo202335n