Reaction:JCGG-RAC0002464

JCGG ID

JCGG-RAC0002464

Submitter

The Noguchi Institute

Reaction ID

R-0000-002464

Regist Date

2012/06/21 19:16:31

REACTANT

MOLECULE ID

JCGG-COM0003200 (Reaction Tree)

Skeleton

JCGG-STR008362

Mol

4.57 mmol

MOLECULE ID

JCGG-COM0000530

Reactant Type

NaOMe (0.5 M in MeOH)

Mol

4.57 mmol

MOLECULE ID

JCGG-COM0000498

Reactant Type

p-TSA

Mol

0.096 mmol

MOLECULE ID

JCGG-COM0000375

Reactant Type

PhCH(OMe)2

Mol

4.81 mmol

PRODUCT

MOLECULE ID

JCGG-COM0003201 (Reaction Tree)

Skeleton

JCGG-STR008362

Yield

77%

REACTION DETAIL

Reaction Time

3 hours, 12 hours

Reaction Temp

0 degree C, room temp

Solvent

dry MeOH (20mL), dry DMF (30mL)

Comment

1) 32+NaOMe, 2) +p-TSA, PhCH(OMe)2

COMMENT

Keywords: triazole, heparosan, chondroitin, copper catalyzed azide-alkyne cycloaddition, CuAAC, azido-glucuronic acid, glucosamine, galactosamine

There are multiple phases in this reaction.

REFERENCE

Reference Id

REF-0000-000343

Issn

Electronic

Doi

10.1021/jo200076z

PubMed ID

21438620

Journal Name

The Journal of organic chemistry. (2011) 76 (9): 3181-93.

Article Title

Design and synthesis of unnatural heparosan and chondroitin building blocks.

Author

Smritilekha, Bera; Robert J, Linhardt

Affiliation

Department of Chemistry and Chemical Biology, Center for Biotechnology and Interdisciplinary Studies, Rensselaer Polytechnic Institute, Troy, New York 12180, USA.

Reference Id

REF-0000-000344

Source

J. Org. Chem. 2011, 76, 3181-3193

Doi

10.1021/jo200076z