Phenoxy-acetic acid (2S,3S,6S)-6-{(2R,3R,4R,6S)-3-acetoxy-6-[(2R,3R,4R,6S)-4-acetoxy-6-(4-methoxy-phenoxy)-2-methyl-tetrahydro-pyran-3-yloxy]-2-methyl-tetrahydro-pyran-4-yloxy}-2-methyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Phenoxy-acetic acid (2S,3S,6S)-6-{(2R,3R,4R,6S)-3-acetoxy-6-[(2R,3R,4R,6S)-4-acetoxy-6-(4-methoxy-phenoxy)-2-methyl-tetrahydro-pyran-3-yloxy]-2-methyl-tetrahydro-pyran-4-yloxy}-2-methyl-tetrahydro-pyran-3-yl ester
• CAS No.: 202919-75-3
• Molecular Formula: C₃₇H₄₈O₁₄
• Molecular Weight: 716.78
• Mol file: 202919-75-3.mol

Synonyms:Phenoxy-acetic acid (2S,3S,6S)-6-{(2R,3R,4R,6S)-3-acetoxy-6-[(2R,3R,4R,6S)-4-acetoxy-6-(4-methoxy-phenoxy)-2-methyl-tetrahydro-pyran-3-yloxy]-2-methyl-tetrahydro-pyran-4-yloxy}-2-methyl-tetrahydro-pyran-3-yl ester

Chemical Property of Phenoxy-acetic acid (2S,3S,6S)-6-{(2R,3R,4R,6S)-3-acetoxy-6-[(2R,3R,4R,6S)-4-acetoxy-6-(4-methoxy-phenoxy)-2-methyl-tetrahydro-pyran-3-yloxy]-2-methyl-tetrahydro-pyran-4-yloxy}-2-methyl-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Phenoxy-acetic acid (2S,3S,6S)-6-{(2R,3R,4R,6S)-3-acetoxy-6-[(2R,3R,4R,6S)-4-acetoxy-6-(4-methoxy-phenoxy)-2-methyl-tetrahydro-pyran-3-yloxy]-2-methyl-tetrahydro-pyran-4-yloxy}-2-methyl-tetrahydro-pyran-3-yl ester

There total 9 articles about Phenoxy-acetic acid (2S,3S,6S)-6-{(2R,3R,4R,6S)-3-acetoxy-6-[(2R,3R,4R,6S)-4-acetoxy-6-(4-methoxy-phenoxy)-2-methyl-tetrahydro-pyran-3-yloxy]-2-methyl-tetrahydro-pyran-4-yloxy}-2-methyl-tetrahydro-pyran-3-yl 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: 92.0%

acetic anhydride (108-24-7) + Phenoxy-acetic acid (2S,3S,6S)-6-{(2R,3R,4R,6S)-3-acetoxy-6-[(2R,3S,4R,6S)-4-hydroxy-6-(4-methoxy-phenoxy)-2-methyl-tetrahydro-pyran-3-yloxy]-2-methyl-tetrahydro-pyran-4-yloxy}-2-methyl-tetrahydro-pyran-3-yl ester (202919-74-2) → Phenoxy-acetic acid (2S,3S,6S)-6-{(2R,3R,4R,6S)-3-acetoxy-6-[(2R,3R,4R,6S)-4-acetoxy-6-(4-methoxy-phenoxy)-2-methyl-tetrahydro-pyran-3-yloxy]-2-methyl-tetrahydro-pyran-4-yloxy}-2-methyl-tetrahydro-pyran-3-yl ester (202919-75-3)

Guidance literature:

With pyridine; dmap; In dichloromethane; for 5h; Ambient temperature;

DOI:10.1021/ja973348b

Reference yield:

(2R,3R,4R)-2-Methyl-4-triethylsilanyloxy-3,4-dihydro-2H-pyran-3-ol → Phenoxy-acetic acid (2S,3S,6S)-6-{(2R,3R,4R,6S)-3-acetoxy-6-[(2R,3R,4R,6S)-4-acetoxy-6-(4-methoxy-phenoxy)-2-methyl-tetrahydro-pyran-3-yloxy]-2-methyl-tetrahydro-pyran-4-yloxy}-2-methyl-tetrahydro-pyran-3-yl ester (202919-75-3)

Guidance literature:

Multi-step reaction with 8 steps

1: toluene

2: toluene / 0 - 20 °C

3: 74 percent / N₂H₄ / methanol / 20 °C

4: 77 percent / 4 Angstroem molecular sieves, DEAD, Ph₃P / toluene / 0 °C

5: 77 percent / Bu₃SnH, AIBN / benzene / Heating

6: 54 percent / TMSOTf / toluene; CH₂Cl₂ / 0.08 h / -94 °C

7: 86 percent / TBAF / tetrahydrofuran / 0.08 h / 0 °C

8: 92 percent / pyridine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 5 h / Ambient temperature

With pyridine; dmap; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; triphenylphosphine; hydrazine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; toluene; benzene;

DOI:10.1021/ja973348b

Reference yield:

(3R,4S,5R,6R)-6-Methyl-3-phenylselanyl-4-triethylsilanyloxy-tetrahydro-pyran-2,5-diol → Phenoxy-acetic acid (2S,3S,6S)-6-{(2R,3R,4R,6S)-3-acetoxy-6-[(2R,3R,4R,6S)-4-acetoxy-6-(4-methoxy-phenoxy)-2-methyl-tetrahydro-pyran-3-yloxy]-2-methyl-tetrahydro-pyran-4-yloxy}-2-methyl-tetrahydro-pyran-3-yl ester (202919-75-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 77 percent / 4 Angstroem molecular sieves, DEAD, Ph₃P / toluene / 0 °C

2: 77 percent / Bu₃SnH, AIBN / benzene / Heating

3: 54 percent / TMSOTf / toluene; CH₂Cl₂ / 0.08 h / -94 °C

4: 86 percent / TBAF / tetrahydrofuran / 0.08 h / 0 °C

5: 92 percent / pyridine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 5 h / Ambient temperature

With pyridine; dmap; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; toluene; benzene;

DOI:10.1021/ja973348b

upstream raw materials:

acetic anhydride

Phenoxy-acetic acid (2S,3S,6S)-6-{(2R,3R,4R,6S)-3-acetoxy-6-[(2R,3S,4R,6S)-4-hydroxy-6-(4-methoxy-phenoxy)-2-methyl-tetrahydro-pyran-3-yloxy]-2-methyl-tetrahydro-pyran-4-yloxy}-2-methyl-tetrahydro-pyran-3-yl ester

(2R,3R,4R,6S)-6-(4-Methoxy-phenoxy)-2-methyl-4-triethylsilanyloxy-tetrahydro-pyran-3-ol

Acetic acid (3R,4S,5R,6R)-5-hydroxy-6-methyl-3-phenylselanyl-4-triethylsilanyloxy-tetrahydro-pyran-2-yl ester

Downstream raw materials:

Acetic acid (2R,3R,4R,6S)-6-[(2R,3R,4R,6S)-4-acetoxy-6-(4-methoxy-phenoxy)-2-methyl-tetrahydro-pyran-3-yloxy]-4-((2S,5S,6S)-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-methyl-tetrahydro-pyran-3-yl ester