Benzoic acid (1S,2S,3R,10R,11R,12R)-11,12-diacetoxy-1-hydroxy-10,14,17,17-tetramethyl-4,15-dioxo-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)-11,12-diacetoxy-1-hydroxy-10,14,17,17-tetramethyl-4,15-dioxo-6-oxa-tricyclo[11.3.1.0^3,10]heptadec-13-en-2-yl ester
• CAS No.: 862251-89-6
• Molecular Formula: C₃₁H₃₈O₁₀
• Molecular Weight: 570.637

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

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

There total 12 articles about Benzoic acid (1S,2S,3R,10R,11R,12R)-11,12-diacetoxy-1-hydroxy-10,14,17,17-tetramethyl-4,15-dioxo-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: 62.0%

C25H32O10 (862251-86-3) + acetic anhydride (108-24-7) + phenyllithium (591-51-5) → Benzoic acid (1S,2S,3R,10R,11R,12R)-11,12-diacetoxy-1-hydroxy-10,14,17,17-tetramethyl-4,15-dioxo-6-oxa-tricyclo[11.3.1.03,10]heptadec-13-en-2-yl ester (862251-89-6)

Guidance literature:

C₂₅H₃₂O₁₀; phenyllithium; In tetrahydrofuran; at -80 ℃;

acetic anhydride; With dmap; In dichloromethane;

DOI:10.1016/j.tetlet.2005.05.071

Reference yield: 58.0%

C25H32O10 (862251-86-3) + phenyllithium (591-51-5) → Benzoic acid (1S,2S,3R,10R,11R,12R)-11,12-diacetoxy-1-hydroxy-10,14,17,17-tetramethyl-4,15-dioxo-6-oxa-tricyclo[11.3.1.03,10]heptadec-13-en-2-yl ester (862251-89-6)

Guidance literature:

In tetrahydrofuran; toluene; at -80 ℃; for 6h;

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)-11,12-diacetoxy-1-hydroxy-10,14,17,17-tetramethyl-4,15-dioxo-6-oxa-tricyclo[11.3.1.03,10]heptadec-13-en-2-yl ester (862251-89-6)

Guidance literature:

Multi-step reaction with 7 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

With pyridine; 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; ethanol; water; toluene; tert-butyl alcohol; benzene;

DOI:10.1016/j.tet.2006.06.080

upstream raw materials:

C₂₅H₃₂O₁₀

acetic anhydride

phenyllithium

C₂₅H₃₁BrO₁₀

Downstream raw materials:

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

(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

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