Methyl-2-deoxy-D-erythropentofuranoside dibenzoate

Base Information

• Chemical Name: Methyl-2-deoxy-D-erythropentofuranoside dibenzoate
• CAS No.: 108647-88-7
• Molecular Formula: C20H20O6
• Molecular Weight: 356.375
• Hs Code.: 2932190090
• Mol file: 108647-88-7.mol

Synonyms:Ribofuranoside,methyl 2-deoxy-, dibenzoate, D- (6CI);

Chemical Property of Methyl-2-deoxy-D-erythropentofuranoside dibenzoate

Chemical Property:

• Appearance/Colour: Colourless solid (gel)
• Boiling Point: 479.061 °C at 760 mmHg
• Flash Point: 209.726 °C
• PSA: 71.06000
• Density: 1.262 g/cm³
• LogP: 2.83040
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate, Methanol

Purity/Quality:

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

Methyl 2-deoxy-3,5-di-O-benzoyl-D-ribofuranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: An intermediate for the production of antiviral and anticancer research chemicals

Technology Process of Methyl-2-deoxy-D-erythropentofuranoside dibenzoate

There total 14 articles about Methyl-2-deoxy-D-erythropentofuranoside dibenzoate 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: 100.0%

benzoyl chloride (98-88-4) + 1-O-methyl-2-deoxy-D-ribofuranoside (51255-17-5,51255-18-6,60134-26-1,89577-26-4,96038-80-1,96039-31-5,144301-84-8,144301-85-9) → ((2R,3S)-3-(benzoyloxy)-5-methoxytetrahydrofuran-2-yl)methyl benzoate (108647-88-7)

Guidance literature:

With pyridine; dmap; triethylamine; at 80 ℃;

DOI:10.1021/ja054607x

Reference yield:

D-2-deoxyribose (452-51-7,13046-70-3,29780-54-9,36792-87-7,36792-88-8,113890-35-0,113890-38-3) → ((2R,3S)-3-(benzoyloxy)-5-methoxytetrahydrofuran-2-yl)methyl benzoate (108647-88-7)

Guidance literature:

Multi-step reaction with 2 steps

1: AcCl / 0.33 h / 20 °C

2: 100 percent / DMAP; Et₃N; pyridine / 80 °C

With pyridine; dmap; triethylamine; acetyl chloride;

DOI:10.1021/ja054607x

Reference yield:

L-arabinose (5328-37-0) → methyl 3,5-di-O-benzoyl-2-deoxy-L-erythro-pentofuranoside (51785-70-7,80339-59-9,102303-03-7,102303-04-8,108647-88-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 49 percent / imidazole / dimethylformamide

2: 67 percent / CuSO₄, H₂SO₄

3: 89 percent / Bu₄NF / tetrahydrofuran

4: 82 percent / pyridine / 3 h / Ambient temperature

5: 89 percent / I₂ / Heating

6: 1) phenyl chlorothionocarbonate, 4-(dimethylamino)pyridine, 2) Bu₃SnH, AIBN / 1) CH₂Cl₂, r.t., 0.5 h, 2) toluene, 80 deg C, 3 h

With pyridine; 1H-imidazole; dmap; 2,2'-azobis(isobutyronitrile); sulfuric acid; tetrabutyl ammonium fluoride; iodine; tri-n-butyl-tin hydride; copper(II) sulfate; phenylcarbonochloridothioate; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(92)84166-P

upstream raw materials:

benzoyl chloride

1-O-methyl-2-deoxy-D-ribofuranoside

D-2-deoxyribose

methanol

Downstream raw materials:

4-amino-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrothiophen-2-yl)pyrimidin-2(1H)-one

1-O-acetyl-3,5-di-O-benzoyl-2-deoxy-D-erythro-pentafuranose

1-(2-deoxy-3,5-di-O-benzoyl-β-L-erythro-pentofuranosyl)-5-fluorouracil

C₂₄H₂₂N₂O₇

Refernces

• 1、 -. "SYNTHETIC INTERMEDIATE OF 1-(2-DEOXY-2-FLUORO-4-THIO-?-D-ARABINOFURANOSYL)CYTOSINE, SYNTHETIC INTERMEDIATE OF THIONUCLEOSIDE, AND METHOD FOR PRODUCING THE SAME". Paragraph 1634-1636. . Retrieved 2015/06/10.
• 2、 Dupradeau, Francois-Yves,Case, David A.,Yu, Chengzhi,Jimenez, Ralph,Romesberg, Floyd E.. "Differential solvation and tautomer stability of a model base pair within the minor and major grooves of DNA". . p. 15612 - 15617. Retrieved 2007/10/03.