(2S,3R,4S,5S,6S)-2-(4-(Hydroxymethyl)-2-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Name: (2S,3R,4S,5S,6S)-2-(4-(Hydroxymethyl)-2-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
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CAS No. 148579-94-6
Cat. No. CS-0142109
Molecule weight485.40
Purity≥96%
MDL No.MFCD30489071

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(2S,3R,4S,5S,6S)-2-(4-(Hydroxymethyl)-2-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate|CS-0142109

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General Information

CAS No. 148579-94-6
Cat. No. CS-0142109
Purity ≥96%
MDL No. MFCD30489071
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₀H₂₃NO₁₃
Molecular Weight 485.40
Synonym(s) β-D-Glucopyranosiduronic acid, 4-(hydroxymethyl)-2-nitrophenyl, methyl ester, 2,3,4-triacetate
SMILES O=C([C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC2=CC=C(CO)C=C2[N+]([O-])=O)O1)OC

Description

This tetrahydro-pyran triacetate derivative features a sterically hindered, bench-stable glycosyl acceptor with orthogonal protection. The para-nitrophenolic moiety enables selective activation, while the triacetate groups facilitate controlled deprotection under mild conditions. This configuration supports efficient glycosylation workflows in complex oligosaccharide synthesis.

Application

This compound serves as a protected glycosyl donor enabling stereoselective glycosylation reactions under mild conditions. The triacetate functionality enhances solubility and stability, while the 2-nitrophenyl ether moiety facilitates activation via Lewis acid catalysis. Its well-defined stereochemistry supports high fidelity coupling in complex oligosaccharide synthesis, with excellent functional group tolerance and straightforward purification.

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GHS Pictogram : N/A	GHS No : N/A
Signal Word : N/A	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : N/A
Precautionary Statements : N/A

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Computational Chemistry Data

TPSA 187.03
LogP 0.1589
H_Acceptors 13
H_Donors 1
Rotatable_Bonds 8

Other Classifications

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Life Science Carbohydrates

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(2S,3R,4S,5S,6S)-2-(4-(Hydroxymethyl)-2-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

CAS No. 148579-94-6

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