Hoffer's chlorosugar

Base Information

• Chemical Name: Hoffer's chlorosugar
• CAS No.: 4330-21-6
• Molecular Formula: C21H21ClO5
• Molecular Weight: 388.848
• Hs Code.: 29321900
• European Community (EC) Number: 224-367-3,800-102-2
• Nikkaji Number: J205.712C
• Wikidata: Q76009736
• ChEMBL ID: CHEMBL3187742
• Mol file: 4330-21-6.mol

Synonyms:Hoffer's chlorosugar;4330-21-6;EINECS 224-367-3;[(2R,3S,5R)-5-chloro-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate;(2R,3S,5R)-5-chloro-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate;3601-89-6;2-Deoxydi(p-toluoyl)-alpha-D-erythro-pentofuranosyl chloride;2-Deoxy-3,5-di-o-p-toluoyl-ribofuranosyl chloride;2-deoxy-3,5-di-o-(p-toluoyl)-alpha-d-erythro-pentofuranosyl chloride;3,5-Di-O-(p-toluyl)-2-deoxy-D-ribofuranosyl chloride;C21H21CLO5;C21-H21-Cl-O5;MFCD01630916;Hoffer'schlorosugar;1-Chloro-2-deoxy-3,5-di-O-toluoyl-D-ribofuranose;SCHEMBL336512;.alpha.-D-erythro-Pentofuranosyl chloride, 2-deoxy-, bis(4-methylbenzoate);CHEMBL3187742;AKOS015895537;CS-W008643;NSC 148837;NCGC00160973-01;3,5-bis(toluoyl)-2-deoxyribosyl chloride;D71205;A826237;3-O,5-O-Di-p-toluoyl-2-deoxy-alpha-D-ribofuranosyl chloride;(2R,3S,5R)-5-chloro-2-((4-methylbenzoyloxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate;[(2R,3S,5R)-5-chloro-3-(4-methylbenzoyloxy)oxolan-2-yl]methyl 4-methylbenzoate

Chemical Property of Hoffer's chlorosugar

Chemical Property:

• Vapor Pressure: 7.5E-11mmHg at 25°C
• Melting Point: 117-119 °C
• Refractive Index: 1.583
• Boiling Point: 518.414 °C at 760 mmHg
• Flash Point: 185.58 °C
• PSA: 27.69000
• Density: 1.28 g/cm³
• LogP: 4.48360
• Storage Temp.: −20°C
• Solubility.: Acetone (Slightly), Chloroform (Slightly), DMSO (Slightly, Sonicated), Methanol
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 388.1077515
• Heavy Atom Count: 27
• Complexity: 509

Purity/Quality:

99% ^*data from raw suppliers

Hoffer''sChlorosugar(~90%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)C(=O)OCC2C(CC(O2)Cl)OC(=O)C3=CC=C(C=C3)C
• Isomeric SMILES: CC1=CC=C(C=C1)C(=O)OC[C@@H]2[C@H](C[C@H](O2)Cl)OC(=O)C3=CC=C(C=C3)C
• Uses: Hoffer''s Chlorosugar is a synthetic precursor for ribose glycosides and ribonucleosides.

Technology Process of Hoffer's chlorosugar

There total 24 articles about Hoffer's chlorosugar which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.0%

methyl 3,5-di-O-toluoyl-2-deoxy-D-ribofuranose (4330-34-1) → 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride (4330-21-6)

Guidance literature:

With acetyl chloride; In acetic acid; at 20 ℃;

DOI:10.1039/b301859h

Reference yield: 72.0%

1-O-methyl-2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranose (78185-64-5) → 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride (4330-21-6)

Guidance literature:

With hydrogenchloride; In diethyl ether; at 0 ℃; for 0.166667h;

DOI:10.1021/ol050709g

Reference yield: 69.0%

D-2-deoxyribose (452-51-7,13046-70-3,29780-54-9,36792-87-7,36792-88-8,113890-35-0,113890-38-3) + 4-methyl-benzoyl chloride (874-60-2) → Hoffer's chlorosugar (3601-89-6,4330-21-6,52304-86-6,3056-12-0,141846-57-3)

Guidance literature:

D-2-deoxyribose; With acetyl chloride; In methanol; at 20 ℃; for 1h;

4-methyl-benzoyl chloride; With pyridine; dmap; at 20 ℃; Cooling with ice;

upstream raw materials:

1-O-methyl-2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranose

methyl 3,5-di-O-toluoyl-2-deoxy-D-ribofuranose

1-O-methyl-2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranose

D-2-deoxyribose

Downstream raw materials:

(furan-2-yl)methyl 4-methylbenzoate

4-Amino-8-<2-desoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-rinofuranosyl>-7(8H)-pteridinon

4-<2-Desoxy-3,5-bis-O-(4-methylbenzoyl)-α-D-ribofuranosylamino>-7(8H)-pteridinon

4-Amino-8-<2-desoxy-3,5-bis-O-(4-methylbenzoyl)-α-D-ribofuranosyl>-2-phenyl-7(8H)-pteridinon

Refernces

• 1、 -. "Benzimidazole derivative BI292 as well as preparation method and application thereof". Paragraph 0019; 0021-0024. . Retrieved 2021/06/09.
• 2、 -. "Synthesis method of desicitabine intermediate alpha-substituted deoxyribose". Paragraph 0037; 0042-0043; 0044; 0049-0051; 0056-0057; 0061. . Retrieved 2019/08/07.