Reaction:JCGG-RAC0001684

JCGG ID

JCGG-RAC0001684

Submitter

The Noguchi Institute

Reaction ID

R-0000-001684

Regist Date

2012/06/21 17:37:04

REACTANT

MOLECULE ID

JCGG-COM0002157 (Reaction Tree)

Mol

1.5 mmol

MOLECULE ID

JCGG-COM0002158 (Reaction Tree)

Mol

1 mmol

MOLECULE ID

JCGG-COM0002159

Reactant Type

(MeS)Me2S+*BF4- (in CH2Cl2)

Mol

2 mmol

MOLECULE ID

JCGG-COM0000426

Reactant Type

DIEA

Mol

1 mmol

PRODUCT

MOLECULE ID

JCGG-COM0002160 (Reaction Tree)

Product Type

alpha

Yield

63%

MOLECULE ID

JCGG-COM0002161 (Reaction Tree)

Skeleton

JCGG-STR028522

Product Type

beta

Yield

19%

REACTION DETAIL

Reaction Time

1 hour, 1 hour, 16 hours, 1 hour

Reaction Temp

20 degree C, 5 degree C, 25 degree C, 25 degree C

Solvent

dry PhCH3, PhCH3/CH2Cl2, PhCH3/CH2Cl2, PhCH3/CH2Cl2

Comment

1) 18+19, MS 4A, 2) +(MeS)Me2S+*BF4-, 3) temperature change, 4) +DIEA

MS 4A was included in the solvent.

COMMENT

Keywords: O-glycopeptide, N-glycopeptide, synthesis, selectively deprotected building blocks, fluorenylmethoxycarbonyl group, Fmoc, benzyl esters

There are multiple steps in this reaction.

ATTENTION: DIEA is mentioned in the written method, but it is not found in the scheme.

REFERENCE

Reference Id

REF-0000-000196

Source

PREPARATIVE CARBOHYDRATE CHEMISTRY

Reference Id

REF-0000-000197

Source

ISBN 0-8247-9802-3

Reference Id

REF-0000-000199

Source

H. Kunz and G. Braum, unpublished results; G. Braum, Synthese von Glycopeptiden mit photoaktivierbaren Gruppen im Saccharidteil, Dissertation, Universitat Mainz, Germany, 1991