1-O-Methyl-3,5-bis-O-[(2,4-dichlorophenyl)methyl]-alpha-D-erthro-pentofuranoside-2-ulose

Base Information

• Chemical Name: 1-O-Methyl-3,5-bis-O-[(2,4-dichlorophenyl)methyl]-alpha-D-erthro-pentofuranoside-2-ulose
• CAS No.: 443642-30-6
• Molecular Formula: C20H18 Cl4 O5
• Molecular Weight: 480.172
• DSSTox Substance ID: DTXSID701133992
• Mol file: 443642-30-6.mol

Synonyms:443642-30-6;1-O-Methyl-3,5-bis-O-[(2,4-dichlorophenyl)methyl]-alpha-D-erthro-pentofuranoside-2-ulose;Methyl 3,5-di-O-(2,4-dichlorobenzyl)-2-keto-a-D-ribofuranoside;(2S,4R,5R)-4-[(2,4-dichlorophenyl)methoxy]-5-[(2,4-dichlorophenyl)methoxymethyl]-2-methoxyoxolan-3-one;VRMGHTPUUVWQSN-RLLQIKCJSA-N;SCHEMBL1737464;DTXSID701133992;(2S,4R,5R)-4-((2,4-dichlorobenzyl)oxy)-5-(((2,4-dichlorobenzyl)oxy)methyl)-2-methoxydihydrofuran-3(2H)-one;(2S,4R,5R)-4-[(2,4-DICHLOROPHENYL)METHOXY]-5-{[(2,4-DICHLOROPHENYL)METHOXY]METHYL}-2-METHOXYOXOLAN-3-ONE;W-202772;3,5-Bis-O-(2,4-dichlorobenzyl)-1-O-methyl-alpha-D-erythro-pentofuranos-2-ulose;3,5-Bis-O-(2,4-dichlorophenylmethyl)-1-O-methyl-alpha-D-erythro-pentofuranos-2-ulose;3,5-bis-O-(2,4-dichlorophenylmethyl)-1-O-methyl-alpha-D-erythro-pentofuranose-2-ulose;Methyl 3,5-bis-O-[(2,4-dichlorophenyl)methyl]-alpha-D-erythro-pentofuranosid-2-ulose

Chemical Property of 1-O-Methyl-3,5-bis-O-[(2,4-dichlorophenyl)methyl]-alpha-D-erthro-pentofuranoside-2-ulose

Chemical Property:

• Boiling Point: 571.0±50.0 °C(Predicted)
• PSA: 53.99000
• Density: 1.45±0.1 g/cm3(Predicted)
• LogP: 5.34260
• XLogP3: 5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 479.987884
• Heavy Atom Count: 29
• Complexity: 539

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methyl3,5-Bis-O-(2,4-dichlorobenzyl)-α-D-erythro-pentofuranosid-2-ulose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C(=O)C(C(O1)COCC2=C(C=C(C=C2)Cl)Cl)OCC3=C(C=C(C=C3)Cl)Cl
• Isomeric SMILES: CO[C@@H]1C(=O)[C@@H]([C@H](O1)COCC2=C(C=C(C=C2)Cl)Cl)OCC3=C(C=C(C=C3)Cl)Cl
• Uses: 1-O-Methyl-3,5-bis-O-[(2,4-dichlorophenyl)methyl]-alpha-D-erthro-pentofuranoside-2-ulose is an intermediate in the synthesis of nucleoside compounds and derivatives suitable for use in treating or prophylaxis of an infection by the SARS virus and/or in treating or prophylaxis of SARS, and for use in inhibiting replication of the SARS virus.

Technology Process of 1-O-Methyl-3,5-bis-O-[(2,4-dichlorophenyl)methyl]-alpha-D-erthro-pentofuranoside-2-ulose

There total 3 articles about 1-O-Methyl-3,5-bis-O-[(2,4-dichlorophenyl)methyl]-alpha-D-erthro-pentofuranoside-2-ulose 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: 90.0%

(3R,4S,5R)-4-((2,4-dichlorobenzyl)oxy)-5-(((2,4-dichlorobenzyl)oxy)methyl)-2-methoxytetrahydrofuran-3-ol (168427-35-8) → 3,5-bis-O-(2,4-dichlorophenylmethyl)-1-O-methyl-α-D-erythro-pentafuranos-2-ulose (443642-30-6)

Guidance literature:

(3R,4S,5R)-4-((2,4-dichlorobenzyl)oxy)-5-(((2,4-dichlorobenzyl)oxy)methyl)-2-methoxytetrahydrofuran-3-ol; With trichloroisocyanuric acid; In dichloromethane; at 0 ℃; for 0.166667h; Inert atmosphere;

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In dichloromethane; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1021/acsmedchemlett.6b00270

Reference yield:

(2R,3R,4R)-3,4-bis((2,4-dichlorobenzyl)oxy)-2-(((2,4-dichlorobenzyl)oxy)methyl)-5-methoxytetrahydrofuran (677299-16-0) → 3,5-bis-O-(2,4-dichlorophenylmethyl)-1-O-methyl-α-D-erythro-pentafuranos-2-ulose (443642-30-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tin(IV) chloride / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

2.1: trichloroisocyanuric acid / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

2.2: 3 h / 20 °C / Inert atmosphere

With trichloroisocyanuric acid; tin(IV) chloride; In dichloromethane;

DOI:10.1021/acsmedchemlett.6b00270

Reference yield:

2-O-acetyl-3,5-bis-O-(2,4-dichlorophenylmethyl)-1-O-methyl-α-D-ribofuranose (168427-36-9) → 3,5-bis-O-(2,4-dichlorophenylmethyl)-1-O-methyl-α-D-erythro-pentafuranos-2-ulose (443642-30-6)

Guidance literature:

Multi-step reaction with 2 steps

1: methanol; potassium carbonate / 0.75 h / 20 °C

2: Dess-Martin periodane / dichloromethane / 73 h / 0 - 20 °C / Inert atmosphere

With methanol; potassium carbonate; Dess-Martin periodane; In dichloromethane;

upstream raw materials:

(3R,4S,5R)-4-((2,4-dichlorobenzyl)oxy)-5-(((2,4-dichlorobenzyl)oxy)methyl)-2-methoxytetrahydrofuran-3-ol

(2R,3R,4R)-3,4-bis((2,4-dichlorobenzyl)oxy)-2-(((2,4-dichlorobenzyl)oxy)methyl)-5-methoxytetrahydrofuran

2-O-acetyl-3,5-bis-O-(2,4-dichlorophenylmethyl)-1-O-methyl-α-D-ribofuranose

Downstream raw materials:

3,5-bis-O-(2,4-dichlorophenylmethyl)-2-C-vinyl-1-O-methyl-α-D-ribofuranose

4-chloro-7-[3,5-bis-O-(2,4-dichlorophenylmethyl)-2-C-ethyl-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine

2-amino-4-cyclopropylamino-7-(2-C-methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

2-amino-4-chloro-7-[3,5-bis-O-(2,4-dichlorophenylmethyl)-2-C,2-O-dimethyl-β-D-ribofuranosyl]-5-methyl-7H-pyrrolo[2,3-d]pyrimidine

Refernces

• 1、 Zeng, Debin,Zhang, Rui,Nie, Quandeng,Cao, Lin,Shang, Luqing,Yin, Zheng. "Discovery of 2'-α-C-Methyl-2'-β-C-fluorouridine Phosphoramidate Prodrugs as Inhibitors of Hepatitis C Virus". supporting information. p. 1197 - 1201. Retrieved 2016/12/18.
• 2、 Eldrup, Anne B.,Prhavc, Marija,Brooks, Jennifer,Bhat, Balkrishen,Prakash, Thazha P.,Song, Quanlai,Bera, Sanjib,Bhat, Neelima,Dande, Prasad,Cook, P. Dan,Bennett, C. Frank,Carroll, Steven S.,Ball, Richard G.,Bosserman, Michele,Burlein, Christine,Colwell, Lawrence F.,Fay, John F.,Flores, Osvaldo A.,Getty, Krista,LaFemina, Robert L.,Leone, Joseph,MacCoss, Malcolm,McMasters, Daniel R.,Tomassini, Joanne E.,Von Langen, Derek,Wolanski, Bohdan,Olsen, David B.. "Structure - activity relationship of heterobase-modified 2′-C-methyl ribonucleosides as inhibitors of hepatitis C virus RNA replication". . p. 5284 - 5297. Retrieved 2007/10/03.