(2R,3R,4S,5S,6R)-2-((Benzoyloxy)methyl)-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate

Name: (2R,3R,4S,5S,6R)-2-((Benzoyloxy)methyl)-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate
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CAS No. 183901-63-5
Cat. No. CS-0448708
Purity≥97%
MDL No.None

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(2R,3R,4S,5S,6R)-2-((Benzoyloxy)methyl)-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate|CS-0448708

Structure of 183901-63-5

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Description

This tribenzoate derivative features a rigid tetrahydropyran core with orthogonal functional handles: a benzoyloxymethyl group at C2, a trichloro-iminoethoxy moiety at C6, and three benzoate esters at C3, C4, and C5. The electron-withdrawing trichloro-imino group enhances electrophilicity at C6, enabling selective transformations under mild conditions. Bench-stable and moisture-tolerant, it serves as a multifunctional scaffold for glycosylation studies and polymer-coupled synthesis workflows.

Application

(2R,3R,4S,5S,6R)-2-((Benzoyloxy)methyl)-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate serves as a highly functionalized glycosyl acceptor in carbohydrate chemistry, enabling stereoselective glycosylation reactions. The trichloro-iminoether group facilitates activation under mild conditions, while the tri-benzoate protection pattern ensures excellent stability and orthogonal deprotection compatibility. Its bench-stable nature and predictable reactivity make it ideal for constructing complex oligosaccharide scaffolds and glycoconjugates in synthetic medicinal chemistry workflows.

General Information

CAS No. 183901-63-5
Cat. No. CS-0448708
Purity ≥97%
MDL No. None
Storage -20°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₃₆H₂₈Cl₃NO₁₀
Molecular Weight 740.97
Synonym(s) None
SMILES C1=CC=C(C=C1)C(=O)OC[C@@H]2[C@H]([C@@H]([C@@H]([C@H](O2)OC(=N)C(Cl)(Cl)Cl)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4)OC(=O)C5=CC=CC=C5

Computational Chemistry Data

TPSA 147.51
LogP 6.60917
H_Acceptors 11
H_Donors 1
Rotatable_Bonds 10

Safety Information

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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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Life Science Carbohydrates

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(2R,3R,4S,5S,6R)-2-((Benzoyloxy)methyl)-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate

CAS No. 183901-63-5

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