Reaction:JCGG-RAC0001447

JCGG ID

JCGG-RAC0001447

Submitter

The Noguchi Institute

Reaction ID

R-0000-001447

Regist Date

2012/06/21 17:04:19

REACTANT

MOLECULE ID

JCGG-COM0001728 (Reaction Tree)

Reactant Type

thioglycoside

Mol

0.18 mmol

MOLECULE ID

JCGG-COM0001729 (Reaction Tree)

Skeleton

JCGG-STR032526

Reactant Type

alcohol

Mol

0.15 mmol

MOLECULE ID

JCGG-COM0000624

Reactant Type

AgOSO2CF3

Mol

0.45 mmol

MOLECULE ID

JCGG-COM0001730

Reactant Type

(Me2N)2CO

Mol

0.30 mmol

MOLECULE ID

JCGG-COM0001650

Reactant Type

Br2

Mol

0.11 mmol

PRODUCT

MOLECULE ID

JCGG-COM0001731 (Reaction Tree)

Skeleton

JCGG-STR018396

Yield

88%

REACTION DETAIL

Reaction Time

20 minutes, 75 minutes

Reaction Temp

room temp, room temp

Solvent

PhCH3, PhCH3

Comment

1) thioglycoside+MS 4A, alcohol, AgOSO2CF3, (Me2N)2CO, 2) +Br2

MS 4A was included in the solvent.

Thioglycoside, alcohol, and MS 4A were mixed and stirred for 4 hours before the reaction.

COMMENT

Keywords: The synthesis of 1,2-cis-glycoside, alpha-glucopyranoside

There are multiple steps in this reaction.

REFERENCE

Reference Id

REF-0000-000073

Source

第4版実験化学講座 (26), 丸善

Reference Id

REF-0000-000074

Source

ISBN 4-621-03702-1

Reference Id

REF-0000-000102

Source

J. O. Kihlberg, D. A. Leigh, and D. R. Bundle, J. Org. Chem., 55, 2860 (1990)