Chloro 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranose

Name: Chloro 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranose
Brand: ChemScene
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CAS No. 3068-34-6
Cat. No. CS-W011811
Purity≥95%
MDL No.MFCD00069776

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FedEx Limited Quantities Ground	$0.00
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Chloro 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranose|CS-W011811

Structure of 3068-34-6

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General Information

CAS No. 3068-34-6
Cat. No. CS-W011811
Purity ≥95%
MDL No. MFCD00069776
Storage -20°C, sealed storage, away from moisture
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₂₀ClNO₈
Molecular Weight 365.76
Synonym(s) None
SMILES CC(O[C@H]1[C@@H]([C@H](O[C@@H]([C@@H]1NC(C)=O)Cl)COC(C)=O)OC(C)=O)=O

Description

Chloro 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranose serves as a key glycosyl donor in oligosaccharide synthesis, featuring a reactive anomeric chloride that enables efficient glycosylation under mild conditions. The tri-O-acetyl protection pattern ensures high regioselectivity, while the acetamido group stabilizes the intermediate oxocarbenium ion. This derivative exhibits excellent shelf stability and handles well under standard anhydrous protocols.

Synthesis

Route1
- In-stock
  
  7512-17-6
- 75-36-5
- ~85%
- In-stock
  
  3068-34-6
References
- Tiwari, Pallavi; Misra, Anup Kumar Carbohydrate Research, 2006 , vol. 341, # 3 p. 339 - 350
Route2
- In-stock
  
  3006-60-8
- ~89%
- In-stock
  
  3068-34-6
References
- Traar, Pedro; Belaj, Ferdinand; Francesconi, Kevin A. Australian Journal of Chemistry, 2004 , vol. 57, # 11 p. 1051 - 1053
Route3
- 14131-68-1
- 75-36-5
- ~90%
- In-stock
  
  3068-34-6
References
- Orth, Ronald; Pitscheider, Maximilian; Sieber, Stephan A. Synthesis, 2010 , # 13 art. no. C01710SS, p. 2201 - 2206

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
Precautionary Statements : P264-P270-P330-P501

Quality Control

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Computational Chemistry Data

TPSA 117.23
LogP -0.1187
H_Acceptors 8
H_Donors 1
Rotatable_Bonds 5

Other Classifications

Bioactive Molecules Dye and Bio-assay Reagents

Life Science Carbohydrates

Chemical Biology Glycoscience Monosaccharides Glucosamines

Chemical Biology Glycoscience Functional Oligosaccharides Glycolipids

Chemical Biology Glycoscience Oligosaccharides by Component Sugar Glucosamine

Chemical Biology Glycoscience Glyco Building Blocks Protected Sugars

Chemical Biology Glycoscience Glyco Building Blocks Glycosyl Donors

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

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

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Chloro 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranose

CAS No. 3068-34-6

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