diMethyl 2-((4R,5S)-5-(2-(benzyloxy)acetyl)-2,2-diMethyl-1,3-dioxolan-4-yl)-2-oxoethylphosphonate

Base Information

• Chemical Name: diMethyl 2-((4R,5S)-5-(2-(benzyloxy)acetyl)-2,2-diMethyl-1,3-dioxolan-4-yl)-2-oxoethylphosphonate
• CAS No.: 89291-74-7
• Molecular Formula: C18H25O8P
• Molecular Weight: 400.36
• Mol file: 89291-74-7.mol

Synonyms:diMethyl 2-((4R,5S)-5-(2-(benzyloxy)acetyl)-2,2-diMethyl-1,3-dioxolan-4-yl)-2-oxoethylphosphonate

Chemical Property of diMethyl 2-((4R,5S)-5-(2-(benzyloxy)acetyl)-2,2-diMethyl-1,3-dioxolan-4-yl)-2-oxoethylphosphonate

Chemical Property:

• PSA: 134.83000
• LogP: 2.69420

Purity/Quality:

≥95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of diMethyl 2-((4R,5S)-5-(2-(benzyloxy)acetyl)-2,2-diMethyl-1,3-dioxolan-4-yl)-2-oxoethylphosphonate

There total 14 articles about diMethyl 2-((4R,5S)-5-(2-(benzyloxy)acetyl)-2,2-diMethyl-1,3-dioxolan-4-yl)-2-oxoethylphosphonate 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: 75.0%

{2-[(4S,5R)-5-((R)-2-Benzyloxy-1-hydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-oxo-ethyl}-phosphonic acid dimethyl ester (89291-71-4) → {2-[(4S,5S)-5-(2-Benzyloxy-acetyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-oxo-ethyl}-phosphonic acid dimethyl ester (89291-74-7)

Guidance literature:

With dipyridine chromium trioxide; In dichloromethane; at 24 ℃; for 1h;

DOI:10.1016/S0040-4039(00)94140-6

Reference yield:

2,3-O-isopropylidene-D-ribonic-γ-lactone (30725-00-9) → (3R,4R)-(-)-6-O-benzyl-1-deoxy-1-(dimethylphosphono)-3,4-O-isopropylidene-D-erythro-2,5-hexodiulose (89291-74-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C

1.2: 78 percent / tetrahydrofuran; hexane / -78 - 20 °C

2.1: 92 percent / sodium hydride / dimethylformamide / 0.5 h / 0 °C

3.1: 77 percent / potassium hydroxide / methanol / 20 h / 20 °C

4.1: 80 percent / pyridine; chromium trioxide / CH₂Cl₂ / 20 °C

With pyridine; chromium(VI) oxide; potassium hydroxide; n-butyllithium; sodium hydride; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: Addition / 2.1: Etherification / 3.1: Hydrolysis / 4.1: Oxidation;

DOI:10.1016/S0040-4020(00)00379-3

Reference yield:

Dimethyl (6-O-benzyl-1-deoxy-3,4-O-isopropylidene-β-D-ribo-hex-2-ulofuranosyl)phosphonate (117251-95-3) → (3R,4R)-(-)-6-O-benzyl-1-deoxy-1-(dimethylphosphono)-3,4-O-isopropylidene-D-erythro-2,5-hexodiulose (89291-74-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / potassium hydroxide / methanol / 20 h / 20 °C

2: 80 percent / pyridine; chromium trioxide / CH₂Cl₂ / 20 °C

With pyridine; chromium(VI) oxide; potassium hydroxide; In methanol; dichloromethane; 1: Hydrolysis / 2: Oxidation;

DOI:10.1016/S0040-4020(00)00379-3

upstream raw materials:

{2-[(4S,5R)-5-((R)-2-Benzyloxy-1-hydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-oxo-ethyl}-phosphonic acid dimethyl ester

5-O-benzyl-2,3-O-isopropylidene-D-ribono-1,4-lactone

Dimethyl (6-O-benzyl-3,4-O-isopropylidene-α-D-ribo-2-hexulofuranosyl)phosphonate

C₃₂H₃₅O₁₀P

Downstream raw materials:

(-)-9-<(1R,4R,5S)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-yl>adenine

(1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol p-toluenesulfonate

(1R,4R,5S)-(-)-1-<(5-amino-6-chloropyrimidinyl)amino>-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopentene

(1R,4R,5S)-(-)-1-azido-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopentene