Benzoic acid (1S,2S,3R,10R,11R,12R,15S)-11,12-diacetoxy-15-((2R,3S)-3-benzoylamino-2-hydroxy-3-phenyl-propionyloxy)-1-hydroxy-10,14,17,17-tetramethyl-4-oxo-6-oxa-tricyclo[11.3.1.0^3,10]heptadec-13-en-2-yl ester

Base Information

• Chemical Name: Benzoic acid (1S,2S,3R,10R,11R,12R,15S)-11,12-diacetoxy-15-((2R,3S)-3-benzoylamino-2-hydroxy-3-phenyl-propionyloxy)-1-hydroxy-10,14,17,17-tetramethyl-4-oxo-6-oxa-tricyclo[11.3.1.0^3,10]heptadec-13-en-2-yl ester
• CAS No.: 862251-88-5
• Molecular Formula: C₄₇H₅₃NO₁₃
• Molecular Weight: 839.937

Synonyms:Benzoic acid (1S,2S,3R,10R,11R,12R,15S)-11,12-diacetoxy-15-((2R,3S)-3-benzoylamino-2-hydroxy-3-phenyl-propionyloxy)-1-hydroxy-10,14,17,17-tetramethyl-4-oxo-6-oxa-tricyclo[11.3.1.0^3,10]heptadec-13-en-2-yl ester

Chemical Property of Benzoic acid (1S,2S,3R,10R,11R,12R,15S)-11,12-diacetoxy-15-((2R,3S)-3-benzoylamino-2-hydroxy-3-phenyl-propionyloxy)-1-hydroxy-10,14,17,17-tetramethyl-4-oxo-6-oxa-tricyclo[11.3.1.0^3,10]heptadec-13-en-2-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of Benzoic acid (1S,2S,3R,10R,11R,12R,15S)-11,12-diacetoxy-15-((2R,3S)-3-benzoylamino-2-hydroxy-3-phenyl-propionyloxy)-1-hydroxy-10,14,17,17-tetramethyl-4-oxo-6-oxa-tricyclo[11.3.1.0^3,10]heptadec-13-en-2-yl ester

There total 15 articles about Benzoic acid (1S,2S,3R,10R,11R,12R,15S)-11,12-diacetoxy-15-((2R,3S)-3-benzoylamino-2-hydroxy-3-phenyl-propionyloxy)-1-hydroxy-10,14,17,17-tetramethyl-4-oxo-6-oxa-tricyclo[11.3.1.0^3,10]heptadec-13-en-2-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: 75.0%

(2R,4S,5R)-3-Benzoyl-2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-5-carboxylic acid (1S,2S,3R,10R,11R,12R,15S)-11,12-diacetoxy-2-benzoyloxy-1-hydroxy-10,14,17,17-tetramethyl-4-oxo-6-oxa-tricyclo[11.3.1.03,10]heptadec-13-en-15-yl ester (911285-72-8) → Benzoic acid (1S,2S,3R,10R,11R,12R,15S)-11,12-diacetoxy-15-((2R,3S)-3-benzoylamino-2-hydroxy-3-phenyl-propionyloxy)-1-hydroxy-10,14,17,17-tetramethyl-4-oxo-6-oxa-tricyclo[11.3.1.03,10]heptadec-13-en-2-yl ester (862251-88-5)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; at 20 ℃; for 0.5h;

DOI:10.1016/j.tetlet.2005.05.071

Reference yield: 75.0%

Benzoic acid (1S,2S,3R,10R,11R,12R,15S)-11,12-diacetoxy-15-[(2R,3S)-3-benzoylamino-2-(4-methoxy-benzyloxy)-3-phenyl-propionyloxy]-1-hydroxy-10,14,17,17-tetramethyl-4-oxo-6-oxa-tricyclo[11.3.1.03,10]heptadec-13-en-2-yl ester → Benzoic acid (1S,2S,3R,10R,11R,12R,15S)-11,12-diacetoxy-15-((2R,3S)-3-benzoylamino-2-hydroxy-3-phenyl-propionyloxy)-1-hydroxy-10,14,17,17-tetramethyl-4-oxo-6-oxa-tricyclo[11.3.1.03,10]heptadec-13-en-2-yl ester (862251-88-5)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; at 20 ℃; for 0.5h;

DOI:10.1016/j.tet.2006.06.080

Reference yield:

9-O,10-O-diacetyl-5-O-cinnamoyl-taxicine 1,2-carbonate → Benzoic acid (1S,2S,3R,10R,11R,12R,15S)-11,12-diacetoxy-15-((2R,3S)-3-benzoylamino-2-hydroxy-3-phenyl-propionyloxy)-1-hydroxy-10,14,17,17-tetramethyl-4-oxo-6-oxa-tricyclo[11.3.1.03,10]heptadec-13-en-2-yl ester (862251-88-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 50 percent / hydroxylamine hydrochloride; Et₃N / tetrahydrofuran; ethanol; H₂O / 30 h / 80 °C

2: pyridine / 24 h / 20 °C

3: NMO; OsO₄ / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 6 h / 20 °C

4: 90 percent / DIPEA / toluene / 24 h / Heating

5: silver acetate; Br₂ / benzene / 0.08 h / UV-irradiation

6: 135 mg / Bu₃SnH; AIBN / benzene / 0.25 h / UV-irradiation

7: 58 percent / tetrahydrofuran; toluene / 6 h / -80 °C

8: 72 percent / NaBH₄ / methanol / 1 h / 20 °C

9: 93 percent / DMAP; DCC / toluene / 0.5 h / 75 °C

10: 75 percent / p-TsOH / methanol / 0.5 h / 20 °C

With pyridine; dmap; sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; 2,2'-azobis(isobutyronitrile); hydroxylamine hydrochloride; bromine; tri-n-butyl-tin hydride; silver(I) acetate; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; ethanol; water; toluene; tert-butyl alcohol; benzene;

DOI:10.1016/j.tet.2006.06.080

upstream raw materials:

(2R,4S,5R)-3-Benzoyl-2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-5-carboxylic acid (1S,2S,3R,10R,11R,12R,15S)-11,12-diacetoxy-2-benzoyloxy-1-hydroxy-10,14,17,17-tetramethyl-4-oxo-6-oxa-tricyclo[11.3.1.0^3,10]heptadec-13-en-15-yl ester

C₂₅H₃₂O₁₀

C₂₅H₃₁BrO₁₀

C₂₅H₃₂O₁₀

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