2,3,5-Tri-O-benzyl-D-ribose

Name: 2,3,5-Tri-O-benzyl-D-ribose
Brand: ChemScene
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CAS No. 54623-25-5
Cat. No. CS-0093272
Molecule weight420.50
Purity≥98%
MDL No.MFCD18070912

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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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General Information

CAS No. 54623-25-5
Cat. No. CS-0093272
Purity ≥98%
MDL No. MFCD18070912
Storage -20°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₆H₂₈O₅
Molecular Weight 420.50
Synonym(s) 2,3,5-Tri-O-benzyl-D-ribofuranose
SMILES O=C[C@H](OCC1=CC=CC=C1)[C@@H]([C@H](O)COCC2=CC=CC=C2)OCC3=CC=CC=C3

Description

2,3,5-Tri-O-benzyl-D-ribose serves as a key glycosyl donor in carbohydrate synthesis, featuring benzyl groups that confer enhanced stability and solubility. The protected hydroxyls enable selective activation at the anomeric center, facilitating efficient glycosylation reactions under mild conditions. This configuration supports stereocontrolled access to complex oligosaccharides and glycoconjugates.

Application

2,3,5-Tri-O-benzyl-D-ribose serves as a key glycosyl donor precursor in carbohydrate chemistry, offering enhanced stability and solubility due to its fully benzylated hydroxyl groups. It facilitates stereoselective glycosylation reactions and functions as a versatile building block for the synthesis of nucleoside analogs and complex oligosaccharides, with predictable reactivity under standard activation conditions.

Synthesis

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  54623-25-5
References
- Schmidt; Karg; Guilliard Chemische Berichte, 1977 , vol. 110, # 7 p. 2433 - 2444

Safety Information

Download SDS

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

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Computational Chemistry Data

TPSA 64.99
LogP 3.9338
H_Acceptors 5
H_Donors 1
Rotatable_Bonds 13

Other Classifications

Bioactive Molecules Dye and Bio-assay Reagents

Building Blocks Functional Group Aldehyde

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Key Words

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2,3,5-Tri-O-benzyl-D-ribose

CAS No. 54623-25-5

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