Benzoic acid (1S,2S,3R,10R,11R,12R,15S)-11,12-diacetoxy-1,15-dihydroxy-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-1,15-dihydroxy-10,14,17,17-tetramethyl-4-oxo-6-oxa-tricyclo[11.3.1.0^3,10]heptadec-13-en-2-yl ester
• CAS No.: 862251-87-4
• Molecular Formula: C₃₁H₄₀O₁₀
• Molecular Weight: 572.653

Synonyms:Benzoic acid (1S,2S,3R,10R,11R,12R,15S)-11,12-diacetoxy-1,15-dihydroxy-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-1,15-dihydroxy-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:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about Benzoic acid (1S,2S,3R,10R,11R,12R,15S)-11,12-diacetoxy-1,15-dihydroxy-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:

9-O,10-O-diacetyl-5-O-cinnamoyl-taxicine 1,2-carbonate → Benzoic acid (1S,2S,3R,10R,11R,12R,15S)-11,12-diacetoxy-1,15-dihydroxy-10,14,17,17-tetramethyl-4-oxo-6-oxa-tricyclo[11.3.1.03,10]heptadec-13-en-2-yl ester (862251-87-4)

Guidance literature:

Multi-step reaction with 8 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

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

DOI:10.1016/j.tet.2006.06.080

Reference yield:

C25H32O10 (862251-86-3) → Benzoic acid (1S,2S,3R,10R,11R,12R,15S)-11,12-diacetoxy-1,15-dihydroxy-10,14,17,17-tetramethyl-4-oxo-6-oxa-tricyclo[11.3.1.03,10]heptadec-13-en-2-yl ester (862251-87-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 58 percent / tetrahydrofuran; toluene / 6 h / -80 °C

2: 72 percent / NaBH₄ / methanol / 1 h / 20 °C

With sodium tetrahydroborate; In tetrahydrofuran; methanol; toluene;

DOI:10.1016/j.tet.2006.06.080

Reference yield:

C25H32O10 (911285-66-0) → Benzoic acid (1S,2S,3R,10R,11R,12R,15S)-11,12-diacetoxy-1,15-dihydroxy-10,14,17,17-tetramethyl-4-oxo-6-oxa-tricyclo[11.3.1.03,10]heptadec-13-en-2-yl ester (862251-87-4)

Guidance literature:

Multi-step reaction with 4 steps

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

2: 135 mg / Bu₃SnH; AIBN / benzene / 0.25 h / UV-irradiation

3: 58 percent / tetrahydrofuran; toluene / 6 h / -80 °C

4: 72 percent / NaBH₄ / methanol / 1 h / 20 °C

With sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); bromine; tri-n-butyl-tin hydride; silver(I) acetate; In tetrahydrofuran; methanol; toluene; benzene;

DOI:10.1016/j.tet.2006.06.080

upstream raw materials:

C₂₅H₃₂O₁₀

C₂₅H₃₁BrO₁₀

C₂₅H₃₂O₁₀

C₂₅H₃₄O₁₁

Downstream 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

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

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