1-Chloro-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose

• CAS: 3601-89-6
• Catalog Number: ACM3601896
• Category: Main Products
• Molecular Weight: 388.85
• Molecular Formula: C21H21ClO5
• Description: The synthesis pathway for the compound '(2R,3S)-5-chloro-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate' involves the protection of the hydroxyl group in the tetrahydrofuran ring, followed by the introduction of the 4-methylbenzoyl group at the C-3 position. The resulting intermediate is then reacted with 4-methylbenzoic acid to form the final product.
• Synonyms: [(2R,3S)-5-chloro-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate
• IUPAC Name: [(2R,3S)-5-chloro-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate
• Canonical SMILES: CC1=CC=C(C=C1)C(=O)OCC2C(CC(O2)Cl)OC(=O)C3=CC=C(C=C3)C
• InChI: InChI=1S/C21H21ClO5/c1-13-3-7-15(8-4-13)20(23)25-12-18-17(11-19(22)26-18)27-21(24)16-9-5-14(2)6-10-16/h3-10,17-19H,11-12H2,1-2H3/t17-,18+,19?/m0/s1
• InChI Key: FJHSYOMVMMNQJQ-PAMZHZACSA-N
• Boiling Point: 518.4±50.0 °C at 760 mmHg
• Melting Point: 109 ºC dec.
• Flash Point: 185.6±29.1 °C
• Density: 1.3±0.1 g/mL
• Solubility: Soluble in Chloroform
• Appearance: Off-white powder
• Application: 2-Deoxy-3,5-di-O-p-toluoyl-D-ribofuranosyl Chloride is a versatile carbohydrate derivative universally used in the preparation of 2'-deoxynucleosides.
• Storage: Store at 2-8 ℃
• Exact Mass: 388.107758
• Hazard Codes: Xi: Irritant
• Isomeric SMILES: CC1=CC=C(C=C1)C(=O)OC[C@@H]2[C@H](CC(O2)Cl)OC(=O)C3=CC=C(C=C3)C
• PSA: 61.83
• Refractive Index: 1.583
• Vapor Pressure: 0.0±1.4 mmHg at 25°C
• XLogP3: 5.23

Case Study

Synthetic Route of DNA Base Analogues via SN2 Reaction at the Anomeric Center of Hoffer's Chlorosugar

Bag S S,et al. Bioorganic & Medicinal Chemistry Letters, 2016, 26(8): 2044-2050.

1-Chloro-2-deoxy-3,5-di-O-toluoyl-a-D-ribofuranoose (also known as Hoffer's chlorosugar) is a synthetic building block used in nucleic acid research that provides a range of α- and β-linked 2 ' -Deoxyribose derivatives.
For example, the SN2 substitution reaction at the anomeric center of Hoffer's chlorosugar with various 5-substituted aromatic tetrazoles in THF in presence of K2CO3 proceeds with regioselectivity at N2-tetrazoles and stereoselectivity at α-chlorosugar with very good yield.

Custom Q&A

What is the molecular formula of 1-Chloro-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose?

The molecular formula is C21H21ClO5.

What is the molecular weight of 1-Chloro-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose?

The molecular weight is 388.8 g/mol.

What is the IUPAC name of 1-Chloro-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose?

The IUPAC name is [(2R,3S,5S)-5-chloro-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate.

What is the InChI of 1-Chloro-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose?

The InChI is InChI=1S/C21H21ClO5/c1-13-3-7-15(8-4-13)20(23)25-12-18-17(11-19(22)26-18)27-21(24)16-9-5-14(2)6-10-16/h3-10,17-19H,11-12H2,1-2H3/t17-,18+,19+/m0/s1.

What is the InChIKey of 1-Chloro-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose?

The InChIKey is FJHSYOMVMMNQJQ-IPMKNSEASA-N.

What is the canonical SMILES of 1-Chloro-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose?

The canonical SMILES is CC1=CC=C(C=C1)C(=O)OCC2C(CC(O2)Cl)OC(=O)C3=CC=C(C=C3)C.

What is the CAS number of 1-Chloro-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose?

The CAS number is 4330-21-6.

What is the EC number of 1-Chloro-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose?

The EC number is 224-367-3.

What is the XLogP3-AA value of 1-Chloro-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose?

The XLogP3-AA value is 4.9.

How many hydrogen bond acceptor counts does 1-Chloro-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose have?

It has 5 hydrogen bond acceptor counts.

Synthetic Use

Upstream Synthesis Route 1

• 4330-34-1

• 3601-89-6

Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 24, p. 8617 - 8626
[2] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 2, p. 207 - 212
[3] Pharmaceutical Chemistry Journal, 1999, vol. 33, # 7, p. 372 - 376
[4] Chemistry Letters, 2004, vol. 33, # 12, p. 1554 - 1555

Upstream Synthesis Route 2

• 452-51-7

• 3601-89-6

Reference: [1] Chemistry Letters, 2004, vol. 33, # 12, p. 1554 - 1555

Downstream Synthesis Route 1

• 931-86-2
• 3601-89-6

• 2353-33-5

Reference: [1] Patent: EP2371825, 2011, A1, . Location in patent: Page/Page column 9

Downstream Synthesis Route 2

• 3601-89-6
• 16727-47-2

• 16727-51-8

Reference: [1]Journal of Medicinal Chemistry,1967,vol. 10,p. 320 - 325

* For details of the synthesis route, please refer to the original source to ensure accuracy.