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

Base Information

• Chemical Name: {2-[(4R,5S)-2,2-Dimethyl-5-(2-trityloxy-acetyl)-[1,3]dioxolan-4-yl]-2-oxo-ethyl}-phosphonic acid dimethyl ester
• CAS No.: 88559-55-1
• Molecular Formula: C₃₀H₃₃O₈P
• Molecular Weight: 552.561

Synonyms:{2-[(4R,5S)-2,2-Dimethyl-5-(2-trityloxy-acetyl)-[1,3]dioxolan-4-yl]-2-oxo-ethyl}-phosphonic acid dimethyl ester

Chemical Property of {2-[(4R,5S)-2,2-Dimethyl-5-(2-trityloxy-acetyl)-[1,3]dioxolan-4-yl]-2-oxo-ethyl}-phosphonic acid dimethyl ester

Chemical Property:

Purity/Quality:

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Technology Process of {2-[(4R,5S)-2,2-Dimethyl-5-(2-trityloxy-acetyl)-[1,3]dioxolan-4-yl]-2-oxo-ethyl}-phosphonic acid dimethyl ester

There total 9 articles about {2-[(4R,5S)-2,2-Dimethyl-5-(2-trityloxy-acetyl)-[1,3]dioxolan-4-yl]-2-oxo-ethyl}-phosphonic acid dimethyl ester 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: 87.0%

{2-[(4R,5R)-5-((R)-1-Hydroxy-2-trityloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-oxo-ethyl}-phosphonic acid dimethyl ester (88559-54-0) → {2-[(4R,5S)-2,2-Dimethyl-5-(2-trityloxy-acetyl)-[1,3]dioxolan-4-yl]-2-oxo-ethyl}-phosphonic acid dimethyl ester (88559-55-1)

Guidance literature:

With dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In dichloromethane; T,time;

DOI:10.1016/S0040-4039(00)88259-3

Reference yield:

2,3-O-isopropylidene-5-O-trityl-D-ribofuranose (54503-64-9,54503-65-0) → {2-[(4R,5S)-2,2-Dimethyl-5-(2-trityloxy-acetyl)-[1,3]dioxolan-4-yl]-2-oxo-ethyl}-phosphonic acid dimethyl ester (88559-55-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 72 percent / sodium borohydride / ethanol / 1 h / 0 °C

2: 87 percent / pyridine / 1 h / 25 °C

3: 84 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

4: 83 percent / n-butyllithium / tetrahydrofuran / 1 h / 0 °C

5: 67 percent / pyridinium chlorochromate, 4A molecular sieves / CH₂Cl₂ / 18 h / 25 °C

6: 64 percent / tetrahydrofuran / 0.5 h / -78 °C

7: 81 percent / DMSO,(CF₃CO)2O,Et₃N / CH₂Cl₂ / T,time

8: 75 percent / tetra-butylammonium fluoride / tetrahydrofuran / 5 h / 54 °C

9: 87 percent / DMSO, (CF₃CO)2O,Et₃N / CH₂Cl₂ / T,time

With pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; n-butyllithium; 4 A molecular sieve; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate; trifluoroacetic anhydride; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1016/S0040-4039(00)88259-3

Reference yield:

2,3-O-isopropylidene-5-O-(triphenylmethyl)-D-ribitol (84709-46-6) → {2-[(4R,5S)-2,2-Dimethyl-5-(2-trityloxy-acetyl)-[1,3]dioxolan-4-yl]-2-oxo-ethyl}-phosphonic acid dimethyl ester (88559-55-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 87 percent / pyridine / 1 h / 25 °C

2: 84 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

3: 83 percent / n-butyllithium / tetrahydrofuran / 1 h / 0 °C

4: 67 percent / pyridinium chlorochromate, 4A molecular sieves / CH₂Cl₂ / 18 h / 25 °C

5: 64 percent / tetrahydrofuran / 0.5 h / -78 °C

6: 81 percent / DMSO,(CF₃CO)2O,Et₃N / CH₂Cl₂ / T,time

7: 75 percent / tetra-butylammonium fluoride / tetrahydrofuran / 5 h / 54 °C

8: 87 percent / DMSO, (CF₃CO)2O,Et₃N / CH₂Cl₂ / T,time

With pyridine; 2,6-dimethylpyridine; n-butyllithium; 4 A molecular sieve; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(00)88259-3

upstream raw materials:

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

2,3-O-isopropylidene-5-O-trityl-D-ribofuranose

2,3-O-isopropylidene-5-O-(triphenylmethyl)-D-ribitol

{(4S,5S)-5-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-trityloxy-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-methanol

Downstream raw materials:

(3aR,6aR)-2,2-dimethyl-6-[(trityloxy)methyl]-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-one

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