(diisopropylphosphonyl)methyl 3,5-bis-O-benzoyl-2-deoxy-β-D-erythro-pentofuranoside

Base Information

• Chemical Name: (diisopropylphosphonyl)methyl 3,5-bis-O-benzoyl-2-deoxy-β-D-erythro-pentofuranoside
• CAS No.: 203172-83-2
• Molecular Formula: C₂₆H₃₃O₉P
• Molecular Weight: 520.516
• Mol file: 203172-83-2.mol

Synonyms:(diisopropylphosphonyl)methyl 3,5-bis-O-benzoyl-2-deoxy-β-D-erythro-pentofuranoside

Chemical Property of (diisopropylphosphonyl)methyl 3,5-bis-O-benzoyl-2-deoxy-β-D-erythro-pentofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (diisopropylphosphonyl)methyl 3,5-bis-O-benzoyl-2-deoxy-β-D-erythro-pentofuranoside

There total 5 articles about (diisopropylphosphonyl)methyl 3,5-bis-O-benzoyl-2-deoxy-β-D-erythro-pentofuranoside 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: 51.0%

diisopropyl hydroxymethylphosphonate (24630-68-0) + ((2R,3S)-3-(benzoyloxy)-5-methoxytetrahydrofuran-2-yl)methyl benzoate (108647-88-7) → (diisopropylphosphonyl)methyl 3,5-bis-O-benzoyl-2-deoxy-β-D-erythro-pentofuranoside (203172-83-2) + (diisopropylphosphonyl)methyl 3,5-bis-O-benzoyl-2-deoxy-α-D-erythro-pentofuranoside (203172-82-1)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 0 ℃; for 4h;

DOI:10.1055/s-1998-1600

Reference yield: 47.0%

3-Trifluoromethyl-benzoic acid (2S,3R,4R,5R)-4-benzoyloxy-5-benzoyloxymethyl-2-(diisopropoxy-phosphorylmethoxy)-tetrahydro-furan-3-yl ester (203172-89-8) → Benzoic acid (2S,5S)-5-(diisopropoxy-phosphorylmethoxy)-tetrahydro-furan-2-ylmethyl ester + (diisopropylphosphonyl)methyl 3,5-bis-O-benzoyl-2-deoxy-β-D-erythro-pentofuranoside (203172-83-2)

Guidance literature:

With magnesium(II) perchlorate; N-methylcarbazole; In water; isopropyl alcohol; at 25 ℃; for 4h; Irradiation;

DOI:10.1055/s-1998-1600

Reference yield:

1,3,5-tri-O-benzoyl-α-D-ribofuranoside (22224-41-5) → (diisopropylphosphonyl)methyl 3,5-bis-O-benzoyl-2-deoxy-β-D-erythro-pentofuranoside (203172-83-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / Ph₃P, DIAD, 2,6-lutidine / dioxane / 12 h / 80 °C

2: 30 percent / TMSOTf / CH₂Cl₂ / 5 h / Ambient temperature

3: 47 percent / Mg(ClO₄)2, N-methylcarbazole / propan-2-ol; H₂O / 4 h / 25 °C / Irradiation

With 2,6-dimethylpyridine; magnesium(II) perchlorate; N-methylcarbazole; trimethylsilyl trifluoromethanesulfonate; di-isopropyl azodicarboxylate; triphenylphosphine; In 1,4-dioxane; dichloromethane; water; isopropyl alcohol;

DOI:10.1055/s-1998-1600

upstream raw materials:

diisopropyl hydroxymethylphosphonate

((2R,3S)-3-(benzoyloxy)-5-methoxytetrahydrofuran-2-yl)methyl benzoate

3-Trifluoromethyl-benzoic acid (2S,3R,4R,5R)-4-benzoyloxy-5-benzoyloxymethyl-2-(diisopropoxy-phosphorylmethoxy)-tetrahydro-furan-3-yl ester

α-D-1,3,5-tri-O-benzoyl-2-O-[3-(trifluoromethyl)benzoyl]ribofuranose

Refernces

• 1、 Rubira, María-José,Pérez-Pérez, María-Jesús,Balzarini, Jan,Camarasa, María-José. "Synthesis of phosphonate analogues of 2-deoxyribose-1-phosphate". . p. 177 - 179. Retrieved 2007/10/03.