(+)-<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

Base Information

• Chemical Name: (+)-<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
• CAS No.: 124553-37-3
• Molecular Formula: C₆₈H₈₂O₉Si
• Molecular Weight: 1071.48

Synonyms:(+)-<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

Chemical Property of (+)-<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

Chemical Property:

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Technology Process of (+)-<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

There total 21 articles about (+)-<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 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: 27.0%

benzoyl chloride (98-88-4) + C61H78O8Si (124553-36-2) → (+)-<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)

Guidance literature:

With pyridine; dmap;

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

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>-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)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 27 percent / py, DMAP

With pyridine; dmap; disodium hydrogenphosphate; sodium amalgam; 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>-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)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 27 percent / py, DMAP

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

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

upstream raw materials:

benzoyl chloride

C₆₁H₇₈O₈Si

C₆₇H₈₄O₁₁SSi

(+)-<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

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-methanol

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

(+)-<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

(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

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