10-deacetoxy-10-morpholinomethyl-7-O-triethylsilylbaccatin III

Base Information

• Chemical Name: 10-deacetoxy-10-morpholinomethyl-7-O-triethylsilylbaccatin III
• CAS No.: 325735-63-5
• Molecular Formula: C₄₀H₅₉NO₁₀Si
• Molecular Weight: 741.995
• Mol file: 325735-63-5.mol

Synonyms:10-deacetoxy-10-morpholinomethyl-7-O-triethylsilylbaccatin III

Chemical Property of 10-deacetoxy-10-morpholinomethyl-7-O-triethylsilylbaccatin III

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 10-deacetoxy-10-morpholinomethyl-7-O-triethylsilylbaccatin III

There total 13 articles about 10-deacetoxy-10-morpholinomethyl-7-O-triethylsilylbaccatin III 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:

triethylsilyl chloride (994-30-9) + C34H45NO10 → 10-deacetoxy-10-morpholinomethyl-7-O-triethylsilylbaccatin III (325735-63-5)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃; for 4h;

DOI:10.3987/COM-00-9051

Reference yield:

10-deacetoxy-10-hydroxypropyl-7-O-triethylsilylbaccatin III (204764-74-9) → 10-deacetoxy-10-morpholinomethyl-7-O-triethylsilylbaccatin III (325735-63-5)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 73 percent / n-Bu₃P / tetrahydrofuran / 2 h / 20 °C

2.1: 81 percent / m-CPBA / tetrahydrofuran / 3 h / 20 °C

3.1: imidazole / dimethylformamide / 2 h / 20 °C

4.1: OsO₄; NMO / tetrahydrofuran; H₂O / 15 h / 20 °C

4.2: NaIO₄ / tetrahydrofuran; methanol; H₂O / 6 h / 20 °C

5.1: 96 percent / NaBH₄ / methanol / 2 h / 0 °C

6.1: 92 percent / n-Bu₃P / tetrahydrofuran / 2 h / 20 °C

7.1: 85 percent / m-CPBA / tetrahydrofuran / 2 h / 20 °C

8.1: OsO₄; NMO / tetrahydrofuran; methanol; H₂O / 18 h

8.2: 96 percent / NaIO₄ / tetrahydrofuran; methanol; H₂O / 13 h / 20 °C

9.1: 85 percent / NaBH₃CN; AcOH / ethanol / 18 h / 20 °C

10.1: HF-Py / pyridine / 12 h / 20 °C

11.1: imidazole / dimethylformamide / 4 h / 0 °C

With 1H-imidazole; sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; tributylphosphine; sodium cyanoborohydride; pyridine hydrogenfluoride; acetic acid; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; pyridine; methanol; ethanol; water; N,N-dimethyl-formamide;

DOI:10.3987/COM-00-9051

Reference yield:

10-deacetoxy-10-(3-methylthiopropyl)-7-O-triethylsilylbaccatin III → 10-deacetoxy-10-morpholinomethyl-7-O-triethylsilylbaccatin III (325735-63-5)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 312 mg / NaIO₄ / methanol; H₂O / 2 h / 0 °C

2.1: 37 percent / Na₂CO₃ / 1,2-dichloro-benzene / 4 h / Heating

3.1: imidazole / dimethylformamide / 2 h / 20 °C

4.1: OsO₄; NMO / tetrahydrofuran; H₂O / 15 h / 20 °C

4.2: NaIO₄ / tetrahydrofuran; methanol; H₂O / 6 h / 20 °C

5.1: 96 percent / NaBH₄ / methanol / 2 h / 0 °C

6.1: 92 percent / n-Bu₃P / tetrahydrofuran / 2 h / 20 °C

7.1: 85 percent / m-CPBA / tetrahydrofuran / 2 h / 20 °C

8.1: OsO₄; NMO / tetrahydrofuran; methanol; H₂O / 18 h

8.2: 96 percent / NaIO₄ / tetrahydrofuran; methanol; H₂O / 13 h / 20 °C

9.1: 85 percent / NaBH₃CN; AcOH / ethanol / 18 h / 20 °C

10.1: HF-Py / pyridine / 12 h / 20 °C

11.1: imidazole / dimethylformamide / 4 h / 0 °C

With 1H-imidazole; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; tributylphosphine; sodium cyanoborohydride; sodium carbonate; pyridine hydrogenfluoride; acetic acid; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; pyridine; methanol; ethanol; water; N,N-dimethyl-formamide; 1,2-dichloro-benzene;

DOI:10.3987/COM-00-9051

upstream raw materials:

triethylsilyl chloride

10-deacetoxy-10-hydroxypropyl-7-O-triethylsilylbaccatin III

10-allyl-10-deacetoxy-7-O-triethylsilylbaccatin III

10-deacetoxy-10-(3-methanesulfinylpropyl)-7-O-triethylsilylbaccatin III

Downstream raw materials:

[2'R,3'S]-13-O-(3-tert-butoxycarbonylamino-2-O-tert-butyldimethylsilyl-3-phenylisoserinyl)-10-deacetoxy-10-morpholinomethyl-7-O-triethylsilylbaccatin III