3,5-O-Bis(4-chlorobenzoyl)-2-deoxy-D-ribofuranosyl chloride

Name: 3,5-O-Bis(4-chlorobenzoyl)-2-deoxy-D-ribofuranosyl chloride
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 3601-90-9
Cat. No. CS-0017828
Purity≥97%
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+
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3,5-O-Bis(4-chlorobenzoyl)-2-deoxy-D-ribofuranosyl chloride|CS-0017828

Structure of 3601-90-9

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General Information

CAS No. 3601-90-9
Cat. No. CS-0017828
Purity ≥97%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₉H₁₅Cl₃O₅
Molecular Weight 429.68
Synonym(s) 1-Chloro-3,5-di-(p-chlorobenzoyl)-2-deoxy-D-ribose
SMILES ClC1C[C@H](OC(C2=CC=C(Cl)C=C2)=O)[C@@H](COC(C3=CC=C(Cl)C=C3)=O)O1

Description

This chlorinated sugar derivative features two 4-chlorobenzoyl groups at the 3,5-positions of the ribofuranose ring, enabling direct conjugation in glycosylation reactions. The anomeric chloride facilitates efficient coupling with nucleophiles under mild conditions, delivering stable glycosidic linkages. Designed for streamlined synthesis of complex oligosaccharides and glycoconjugates, this reagent combines high reactivity with bench-stable handling.

Application

3,5-O-Bis(4-chlorobenzoyl)-2-deoxy-D-ribofuranosyl chloride serves as a versatile glycosyl donor in oligosaccharide synthesis, enabling efficient α-selective glycosylation reactions. The 4-chlorobenzoyl groups provide enhanced stability and solubility, while the anomeric chloride facilitates controlled activation under mild conditions. Its functional group tolerance and predictable reactivity make it ideal for constructing complex carbohydrate architectures with high stereoselectivity and reproducibility in synthetic workflows.

Synthesis

Route1
- 452-51-7
- 122-01-0
- ~82%
- In-stock
  
  3601-90-9
References
- Journal of Organic Chemistry, , vol. 69, # 22 p. 7543 - 7551
Route2
- 122-01-0
- 80184-05-0
- ~%
- In-stock
  
  3601-90-9
References
- Tetrahedron, , vol. 50, # 28 p. 8371 - 8380
Route3
- 452-51-7
- ~%
- In-stock
  
  3601-90-9
References
- Tetrahedron, , vol. 50, # 28 p. 8371 - 8380

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-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 61.83
LogP 4.7296
H_Acceptors 5
H_Donors 0
Rotatable_Bonds 5

Other Classifications

Building Blocks Functional Group Chloride

Building Blocks Functional Group Ester

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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3,5-O-Bis(4-chlorobenzoyl)-2-deoxy-D-ribofuranosyl chloride

CAS No. 3601-90-9

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