2,3,4,6-Tetra-O-benzyl-D-glucopyranose

Name: 2,3,4,6-Tetra-O-benzyl-D-glucopyranose
Brand: ChemScene
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CAS No. 4132-28-9
Cat. No. CS-W011467
Purity≥98%
MDL No.None

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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2,3,4,6-Tetra-O-benzyl-D-glucopyranose|CS-W011467

Structure of 4132-28-9

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General Information

CAS No. 4132-28-9
Cat. No. CS-W011467
Purity ≥98%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₃₄H₃₆O₆
Molecular Weight 540.65
Synonym(s) 2,3,4,6-Tetrakis-O-(phenylmethyl)-D-glucopyranose
SMILES OC([C@@H]1OCC2=CC=CC=C2)O[C@H](COCC3=CC=CC=C3)[C@@H](OCC4=CC=CC=C4)[C@@H]1OCC5=CC=CC=C5

Description

This tetra-O-benzyl-protected glucopyranose features four benzyl ethers stabilizing the pyranose ring, enabling robust handling and selective deprotection in synthetic glycosylation workflows. The orthogonal protection pattern supports sequential functionalization at C2, C3, C4, and C6 positions, facilitating precise access to complex oligosaccharide architectures under standard conditions.

Application

2,3,4,6-Tetra-O-benzyl-D-glucopyranose serves as a robust glycosyl donor scaffold in carbohydrate synthesis, offering enhanced stability and orthogonal protection for selective glycosylation reactions. Its benzyl groups provide excellent functional group tolerance and facilitate purification, while the pyranose ring enables reliable stereoselective coupling under standard activation conditions. This compound functions as a key building block for complex oligosaccharides and glycoconjugates in medicinal chemistry and materials science applications.

Synthesis

Route1
- 78136-20-6
- ~0%
- 4291-69-4
- 78184-89-1
- In-stock
  
  4132-28-9
References
- Helleur, Robert; Rao, Vanga S.; Perlin, Arthur S. Carbohydrate Research, 1981 , vol. 89, p. 83 - 90
Route2
- 99388-26-8
- ~%
- 4291-69-4
- 1138154-24-1
- 24679-79-6
- In-stock
  
  4132-28-9
References
- Cribiu, Riccardo; Eszter Borbas; Cumpstey, Ian Tetrahedron, 2009 , vol. 65, # 10 p. 2022 - 2031

Safety Information

Download SDS

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

Quality Control

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Computational Chemistry Data

TPSA 66.38
LogP 5.6766
H_Acceptors 6
H_Donors 1
Rotatable_Bonds 13

Other Classifications

Bioactive Molecules Dye and Bio-assay Reagents

Life Science Carbohydrates

Chemical Biology Pharmaceutical Development and Drug Discovery Research Conjugation Chemistry/Click Chemistry Aldehyde Reactive Fluorophores and Labels

Chemical Biology Glycoscience Glyco Building Blocks Protected Sugars

Chemical Biology Glycoscience Glyco Building Blocks Sugar Building Blocks by Target Oligosaccharides

Chemical Biology Glycoscience Monosaccharides Glucoses

Key Words

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2,3,4,6-Tetra-O-benzyl-D-glucopyranose

CAS No. 4132-28-9

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