(3R,4S,5R,6R)-3,4,5-Tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

Name: (3R,4S,5R,6R)-3,4,5-Tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
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CAS No. 32384-65-9
Cat. No. CS-M2269
Purity≥95%
MDL No.MFCD22665922

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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(3R,4S,5R,6R)-3,4,5-Tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one|CS-M2269

Structure of 32384-65-9

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General Information

CAS No. 32384-65-9
Cat. No. CS-M2269
Purity ≥95%
MDL No. MFCD22665922
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₈H₄₂O₆Si₄
Molecular Weight 466.86
Synonym(s) None
SMILES O=C1[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O1

Description

This tetrahydro-pyranone derivative features four trimethylsilyl ether groups that confer exceptional stability and solubility in organic media. The protected hydroxyl functionalities enable reliable use in multistep carbohydrate synthesis, where the silyl moieties serve as orthogonal masking groups. This compound functions as a key building block for complex glycosyl donors and advanced oligosaccharide assembly.

Application

(3R,4S,5R,6R)-3,4,5-Tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one serves as a highly functionalized glycal equivalent, enabling efficient access to complex oligosaccharide building blocks. Its multiple silyl ether groups confer excellent bench stability and orthogonal deprotection profiles, facilitating sequential transformations in stereoselective glycosylation workflows. The C6 aldehyde functionality reacts readily with nucleophiles under mild conditions, while the protected hydroxyls tolerate a broad range of reaction conditions, making it a versatile scaffold for carbohydrate synthesis and natural product derivatization.

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 63.22
LogP 4.4236
H_Acceptors 6
H_Donors 0
Rotatable_Bonds 9

Other Classifications

Material Science Organic-Inorganic Hybrid Materials A silane coupling agent

Chemical Biology Glycoscience Monosaccharides Glucoses

Key Words

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(3R,4S,5R,6R)-3,4,5-Tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

CAS No. 32384-65-9

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