22224-41-5 | 1,3,5-Tri-O-benzoyl-alpha-D-ribofuranose

Packsize	Purity	Availability	Price	Discounted Price
1g	98%	in stock	$8.00	$5.00
5g	98%	in stock	$22.00	$15.00
10g	98%	in stock	$30.00	$21.00
100g	98%	in stock	$83.00	$58.00

Description

• Catalog Number: AI45276
• Chemical Name: 1,3,5-Tri-O-benzoyl-alpha-D-ribofuranose
• CAS Number: 22224-41-5
• Molecular Formula: C26H22O8
• Molecular Weight: 462.4481
• MDL Number: MFCD00080818
• SMILES: O[C@H]1[C@H](O[C@@H]([C@H]1OC(=O)c1ccccc1)COC(=O)c1ccccc1)OC(=O)c1ccccc1

Computed Properties

• Complexity: 691
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 4
• Heavy Atom Count: 34
• Hydrogen Bond Acceptor Count: 8
• Hydrogen Bond Donor Count: 1
• Rotatable Bond Count: 10
• XLogP3: 4.2

Upstream Synthesis Route

1,3,5-Tri-O-benzoyl-α-D-ribofuranose, a key compound in chemical synthesis, plays a crucial role in various transformations and reactions within organic chemistry. It is commonly utilized as a protecting group due to its ability to shield the hydroxyl groups of the ribofuranose moiety. By masking these functional groups, 1,3,5-Tri-O-benzoyl-α-D-ribofuranose enables selective modifications at other sites of the molecule without interference.Furthermore, this compound serves as a versatile building block in the synthesis of complex carbohydrates and natural products. Its strategic placement and subsequent removal allow for precise control over the regioselectivity and stereochemistry of reactions, facilitating the construction of intricate molecular structures. Additionally, the benzoyl groups provide stability and facilitate purification processes during the synthesis of target compounds.Overall, 1,3,5-Tri-O-benzoyl-α-D-ribofuranose is a valuable tool in organic synthesis, aiding chemists in the design and assembly of diverse molecules with specific functional groups and stereochemical configurations.

Literature

• Synthesis of 2'-C-beta-methyl-2'-deoxyguanosine.

  The Journal of organic chemistry 20090306

• Synthesis of 2'-C-difluoromethylribonucleosides and their enzymatic incorporation into oligonucleotides.

  The Journal of organic chemistry 20050930

• 2'-C-branched ribonucleosides. 2. Synthesis of 2'-C-beta-trifluoromethyl pyrimidine ribonucleosides.

  Organic letters 20010405