Reaction:JCGG-RAC0001377

JCGG ID

JCGG-RAC0001377

Submitter

The Noguchi Institute

Reaction ID

R-0000-001377

Regist Date

2012/06/21 16:55:54

REACTANT

MOLECULE ID

JCGG-COM0001572 (Reaction Tree)

Skeleton

JCGG-STR001961

Reactant Type

id=14 (in 4 mL of THF)

Mol

0.395 mmol

MOLECULE ID

JCGG-COM0001581

Reactant Type

TMS2NK (0.5 M in PhCH3)

Volume

1.90 mL

MOLECULE ID

JCGG-COM0001582

Reactant Type

HS(CH2)nSH

Mol

3 equiv. (approximately)

MOLECULE ID

JCGG-COM0001583

Reactant Type

HMPA

Volume

4 mL

MOLECULE ID

JCGG-COM0000086

Reactant Type

Ac2O

Volume

1 mL

MOLECULE ID

JCGG-COM0000979

Reactant Type

pyridine

Volume

2 mL

PRODUCT

MOLECULE ID

JCGG-COM0001595 (Reaction Tree)

Yield

78%

MOLECULE ID

JCGG-COM0001596 (Reaction Tree)

Yield

15%

REACTION DETAIL

Reaction Time

NOT specified, 30 minutes, 2 hours, 12 hours

Reaction Temp

-78 degree C, -78 degree C, ambient temperature, ambient temperature

Solvent

THF, THF, THF, THF

Comment

1) +TMS2NK, and degassed, 2) +HS(CH2)nSH, HMPA, and degassed, 3) +14, and degassed, 4) +Ac2O, pyridine

The reactants were mixed at -78 degree in Celsius, and gradually allowed to warm to ambient temperature. (third phase, after being degassed)

COMMENT

Keywords: Bisubstrate-type sialyltransferase inhibitors, CMP-NeuAc, N-acetyllactosamine, lactose, sialic acid, ST6N, ST3N

There are multiple phases in this reaction.

REFERENCE

Reference Id

REF-0000-000071

Issn

Doi

10.1021/jo030042g

PubMed ID

12839452

Journal Name

The Journal of organic chemistry. (2003) 68 (14): 5602-13.

Article Title

Systematic syntheses and inhibitory activities of bisubstrate-type inhibitors of sialyltransferases.

Author

Hiroshi, Hinou; Xue-Long, Sun; Yukishige, Ito

Affiliation

RIKEN (The Institute of Physical and Chemical Research), 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan.

Reference Id

REF-0000-000072

Source

J. Org. Chem. 2003, 68, 5602-5613

Doi

10.1021/jo030042g