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Benzyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside

  • CAS No. 59935-49-8

  • Cat. No. CS-0098065
  • Purity≥97%
  • MDL No.None

*For research and further manufacturing use only, not for direct human use.

Benzyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside|CS-0098065

Structure of 59935-49-8

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General Information

  • CAS No. 59935-49-8
  • Cat. No. CS-0098065
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₃₄H₃₆O₆
  • Molecular Weight 540.65
  • Synonym(s) BENZYL 2,3,4-TRI-O-BENZYL-A-D-GLUCOPYRANOSIDE
  • SMILES OC[C@H]1O[C@H](OCC2=CC=CC=C2)[C@H](OCC3=CC=CC=C3)[C@@H](OCC4=CC=CC=C4)[C@@H]1OCC5=CC=CC=C5

Description

Benzyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside serves as a protected glycosyl donor in carbohydrate synthesis, featuring three benzyl ether groups that confer enhanced stability and solubility. The α-configured glycosidic linkage enables stereoselective coupling reactions under standard activation conditions. This derivative integrates readily into complex oligosaccharide architectures with minimal side reactivity.

Application

Benzyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside serves as a versatile glycosyl building block in carbohydrate chemistry, enabling reliable glycosylation reactions through its protected hydroxyl groups and stable benzylated anomeric center. Its bench-stable nature, high functional group tolerance, and compatibility with standard coupling conditions make it ideal for constructing complex oligosaccharides and glycoconjugates in medicinal chemistry and synthetic glycan research.

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   66.38
  • LogP   5.6766
  • H_Acceptors   6
  • H_Donors   1
  • Rotatable_Bonds   13

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