(E)-(10R,11S,12R)-13-Benzyloxy-11-hydroxy-10,12-dimethyl-7-oxo-tridec-2-enoic acid ethyl ester

Base Information

Chemical Name:(E)-(10R,11S,12R)-13-Benzyloxy-11-hydroxy-10,12-dimethyl-7-oxo-tridec-2-enoic acid ethyl ester
CAS No.:207572-42-7
Molecular Formula:C₂₄H₃₆O₅
Molecular Weight:404.547
Hs Code.:

Synonyms:(E)-(10R,11S,12R)-13-Benzyloxy-11-hydroxy-10,12-dimethyl-7-oxo-tridec-2-enoic acid ethyl ester

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Chemical Property of (E)-(10R,11S,12R)-13-Benzyloxy-11-hydroxy-10,12-dimethyl-7-oxo-tridec-2-enoic acid ethyl ester

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Technology Process of (E)-(10R,11S,12R)-13-Benzyloxy-11-hydroxy-10,12-dimethyl-7-oxo-tridec-2-enoic acid ethyl ester

There total 8 articles about (E)-(10R,11S,12R)-13-Benzyloxy-11-hydroxy-10,12-dimethyl-7-oxo-tridec-2-enoic acid ethyl 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: 71.0%

: 207572-41-6
(E)-(10R,11S,12R)-13-Benzyloxy-11-(tert-butyl-dimethyl-silanyloxy)-10,12-dimethyl-7-oxo-tridec-2-enoic acid ethyl ester

: 207572-42-7
(E)-(10R,11S,12R)-13-Benzyloxy-11-hydroxy-10,12-dimethyl-7-oxo-tridec-2-enoic acid ethyl ester

Guidance literature:: With pyridine hydrogenfluoride; In tetrahydrofuran; for 12h;
DOI:10.1016/S0040-4039(98)00320-7

Reference yield:

: 125873-80-5
((2S,3R)-3-((R)-1-(benzyloxy)propan-2-yl)oxiran-2-yl)methanol

: 207572-42-7
(E)-(10R,11S,12R)-13-Benzyloxy-11-hydroxy-10,12-dimethyl-7-oxo-tridec-2-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: CrO₃, py / CH₂Cl₂ / 0 °C

2: benzene / Ambient temperature

3: 85 percent / H₂O; CH₂Cl₂ / -30 °C

4: 95 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

5: 95 percent / Mg / methanol / Ambient temperature

6: DIBAL-H / CH₂Cl₂ / -78 °C

7: 78 percent / Mg / diethyl ether / 0 °C

8: 76 percent / PCC / CH₂Cl₂ / 0 °C

9: 1.) O₃, Ph₃P / 1.) CH₂Cl₂, -78 deg C, 2.) C₆H₆, r.t.

10: 71 percent / HF-py / tetrahydrofuran / 12 h

With pyridine; 2,6-dimethylpyridine; chromium(VI) oxide; diisobutylaluminium hydride; pyridine hydrogenfluoride; ozone; magnesium; triphenylphosphine; pyridinium chlorochromate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; benzene;
DOI:10.1016/S0040-4039(98)00320-7

Reference yield:

: 179944-92-4
(E)-(4R,5S,6R)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-hept-2-enoic acid ethyl ester

: 207572-42-7
(E)-(10R,11S,12R)-13-Benzyloxy-11-hydroxy-10,12-dimethyl-7-oxo-tridec-2-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 95 percent / Mg / methanol / Ambient temperature

2: DIBAL-H / CH₂Cl₂ / -78 °C

3: 78 percent / Mg / diethyl ether / 0 °C

4: 76 percent / PCC / CH₂Cl₂ / 0 °C

5: 1.) O₃, Ph₃P / 1.) CH₂Cl₂, -78 deg C, 2.) C₆H₆, r.t.

6: 71 percent / HF-py / tetrahydrofuran / 12 h

With diisobutylaluminium hydride; pyridine hydrogenfluoride; ozone; magnesium; triphenylphosphine; pyridinium chlorochromate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;
DOI:10.1016/S0040-4039(98)00320-7