(+)-<2R,5E<2E,4R,6E,8(2R,4S,6S,8R,9S)>,6S,8S,9S,11S>-10-benzoyloxy-5-<(4-benzoyloxy-8,9-dimethyl-1,7-dioxaspiro<5.5>undecan-2-yl)-4,6-dimethyl-2,6-octadienylidene>-9-methyl-2-phenyl-1,3-dioxaspiro<5.5>undecane-7-methanol

Base Information

• Chemical Name: (+)-<2R,5E<2E,4R,6E,8(2R,4S,6S,8R,9S)>,6S,8S,9S,11S>-10-benzoyloxy-5-<(4-benzoyloxy-8,9-dimethyl-1,7-dioxaspiro<5.5>undecan-2-yl)-4,6-dimethyl-2,6-octadienylidene>-9-methyl-2-phenyl-1,3-dioxaspiro<5.5>undecane-7-methanol
• CAS No.: 127785-60-8
• Molecular Formula: C₅₂H₆₄O₉
• Molecular Weight: 833.075

Synonyms:(+)-<2R,5E<2E,4R,6E,8(2R,4S,6S,8R,9S)>,6S,8S,9S,11S>-10-benzoyloxy-5-<(4-benzoyloxy-8,9-dimethyl-1,7-dioxaspiro<5.5>undecan-2-yl)-4,6-dimethyl-2,6-octadienylidene>-9-methyl-2-phenyl-1,3-dioxaspiro<5.5>undecane-7-methanol

Chemical Property of (+)-<2R,5E<2E,4R,6E,8(2R,4S,6S,8R,9S)>,6S,8S,9S,11S>-10-benzoyloxy-5-<(4-benzoyloxy-8,9-dimethyl-1,7-dioxaspiro<5.5>undecan-2-yl)-4,6-dimethyl-2,6-octadienylidene>-9-methyl-2-phenyl-1,3-dioxaspiro<5.5>undecane-7-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-<2R,5E<2E,4R,6E,8(2R,4S,6S,8R,9S)>,6S,8S,9S,11S>-10-benzoyloxy-5-<(4-benzoyloxy-8,9-dimethyl-1,7-dioxaspiro<5.5>undecan-2-yl)-4,6-dimethyl-2,6-octadienylidene>-9-methyl-2-phenyl-1,3-dioxaspiro<5.5>undecane-7-methanol

There total 22 articles about (+)-<2R,5E<2E,4R,6E,8(2R,4S,6S,8R,9S)>,6S,8S,9S,11S>-10-benzoyloxy-5-<(4-benzoyloxy-8,9-dimethyl-1,7-dioxaspiro<5.5>undecan-2-yl)-4,6-dimethyl-2,6-octadienylidene>-9-methyl-2-phenyl-1,3-dioxaspiro<5.5>undecane-7-methanol 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: 91.0%

(+)-<2R,5E<2E,4R,6E,8(2R,4S,6S,8R,9S)>,6S,8S,9S,11S>-5-<(4-benzoyloxy-8,9-dimethyl-1,7-dioxaspiro<5.5>undecan-2-yl)-4,6-dimethyl-2,6-octadienylidene>-11-<(tert-butyldiphenylsilyloxy)methyl>-9-methyl-2-phenyl-1,3-dioxaspiro<5.5>undecan-8-ol (124553-37-3) → (+)-<2R,5E<2E,4R,6E,8(2R,4S,6S,8R,9S)>,6S,8S,9S,11S>-10-benzoyloxy-5-<(4-benzoyloxy-8,9-dimethyl-1,7-dioxaspiro<5.5>undecan-2-yl)-4,6-dimethyl-2,6-octadienylidene>-9-methyl-2-phenyl-1,3-dioxaspiro<5.5>undecane-7-methanol (127785-60-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.25h; Heating;

DOI:10.1016/S0040-4020(01)89182-1

Reference yield:

(+)-<2R,4E,6(2R,4S,6S,8R,9S)>-6-(4-benzoyloxy-8,9-dimethyl-1,7-dioxaspiro<5.5>undecan-2-yl)-2,4-dimethyl-4-hexenal (115031-05-5) → (+)-<2R,5E<2E,4R,6E,8(2R,4S,6S,8R,9S)>,6S,8S,9S,11S>-10-benzoyloxy-5-<(4-benzoyloxy-8,9-dimethyl-1,7-dioxaspiro<5.5>undecan-2-yl)-4,6-dimethyl-2,6-octadienylidene>-9-methyl-2-phenyl-1,3-dioxaspiro<5.5>undecane-7-methanol (127785-60-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 83 percent / t-butyl lithium / tetrahydrofuran / -78 °C

2: sodium amalgam, Na₂HPO₄ / tetrahydrofuran; methanol / -40 °C

3: 27 percent / py, DMAP

4: 91 percent / TBAF / tetrahydrofuran / Heating

With pyridine; dmap; disodium hydrogenphosphate; sodium amalgam; tetrabutyl ammonium fluoride; tert.-butyl lithium; In tetrahydrofuran; methanol;

DOI:10.1016/S0040-4039(00)99203-7

Reference yield:

(+)-(2R,5S(E),6S,8S,9S,11S)-11-<(tert-butyldiphenylsilyloxy)methyl>-9-methyl-2-phenyl-5-<2-(phenylsulphonyl)ethenyl>-1,3-dioxaspiro<5.5>undecan-8-ol (115030-97-2,124600-50-6) → (+)-<2R,5E<2E,4R,6E,8(2R,4S,6S,8R,9S)>,6S,8S,9S,11S>-10-benzoyloxy-5-<(4-benzoyloxy-8,9-dimethyl-1,7-dioxaspiro<5.5>undecan-2-yl)-4,6-dimethyl-2,6-octadienylidene>-9-methyl-2-phenyl-1,3-dioxaspiro<5.5>undecane-7-methanol (127785-60-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 83 percent / t-butyl lithium / tetrahydrofuran / -78 °C

2: sodium amalgam, Na₂HPO₄ / tetrahydrofuran; methanol / -40 °C

3: 27 percent / py, DMAP

4: 91 percent / TBAF / tetrahydrofuran / Heating

With pyridine; dmap; disodium hydrogenphosphate; sodium amalgam; tetrabutyl ammonium fluoride; tert.-butyl lithium; In tetrahydrofuran; methanol;

DOI:10.1016/S0040-4039(00)99203-7

upstream raw materials:

(+)-<2R,5E<2E,4R,6E,8(2R,4S,6S,8R,9S)>,6S,8S,9S,11S>-5-<(4-benzoyloxy-8,9-dimethyl-1,7-dioxaspiro<5.5>undecan-2-yl)-4,6-dimethyl-2,6-octadienylidene>-11-<(tert-butyldiphenylsilyloxy)methyl>-9-methyl-2-phenyl-1,3-dioxaspiro<5.5>undecan-8-ol

(+)-<2R,4E,6(2R,4S,6S,8R,9S)>-6-(4-benzoyloxy-8,9-dimethyl-1,7-dioxaspiro<5.5>undecan-2-yl)-2,4-dimethyl-4-hexenal

C₆₁H₇₈O₈Si

(+)-(2R,5S(E),6S,8S,9S,11S)-11-<(tert-butyldiphenylsilyloxy)methyl>-9-methyl-2-phenyl-5-<2-(phenylsulphonyl)ethenyl>-1,3-dioxaspiro<5.5>undecan-8-ol

Downstream raw materials:

(+)-<2R,5E<2E,4R,6E,8(2R,4S,6S,8R,9S)>,6S,8S,9S,11S>-10-benzoyloxy-5-<(4-benzoyloxy-8,9-dimethyl-1,7-dioxaspiro<5.5>undecan-2-yl)-4,6-dimethyl-2,6-octadienylidene>-9-methyl-2-phenyl-1,3-dioxaspiro<5.5>undecane-7-carboxaldehyde

(+)-8'O-(tert-butyldimethylsilyl)-5-desmethoxy-3,4-dihydro-5-oxo-4-(phenylselenenyl)milbemycin β₁

(2R,6S,7R,9S,10S)-10-Benzoyloxy-5-[(2E,6E)-(R)-8-((2R,4S,6R,8R,9S)-4-benzoyloxy-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl)-4,6-dimethyl-octa-2,6-dien-(E)-ylidene]-9-methyl-2-phenyl-1,3-dioxa-spiro[5.5]undecane-7-carboxylic acid

(+)-milbemycin β₁

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