(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

Base Information

• Chemical Name: (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
• CAS No.: 124553-38-4
• Molecular Formula: C₅₂H₆₂O₁₀
• Molecular Weight: 847.058

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 29 articles about (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 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:

(-)-(2S,4S,5S)-2-<(tert-butyldiphenylsilyloxy)methyl>-5-hydroxy-4-methylcyclohexanone (116511-47-8) → (2R,6S,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 (124553-38-4)

Guidance literature:

Multi-step reaction with 11 steps

1: 87 percent / tert-butyl-lithium / diethyl ether; tetrahydrofuran / 1 h / -78 °C

2: 1.) mCPBA; 2.) oxone / 1.) CH₂Cl₂, 0 deg C, 10 min; 2.) methanol/THF/H₂O, 0 deg C, 5 h

3: 1.) BH₃*DMS; 2.) aq. NaOH, H₂O₂ / 1.) THF, 0 deg C, --> room temp., 16 h; 2.) H₂O, 30 min

4: 45 percent / pyridinium-p-toluene sulphonate / benzene / 1 h / Heating; Dean-Stark conditions

5: 1.) n-butyllithium / 1.) hexanes, THF, -78 deg C, 15 min; 2.) -78 deg C, 1 h

6: 99 percent / mCPBA, sat. sodium hydrogencarbonate / CH₂Cl₂ / 0.75 h / 10 °C

7: 84 percent / 1.) tert-butyllithium / tetrahydrofuran / 1 h / -78 °C / 1.) -78 deg C, 10 min

8: 1.) 6percentsodium amalgam, Na₂HPO₄; 2.) DMAP / 1.) THF/MeOH, -40 deg C, 70 min; 2.) CH₂Cl₂, pyridine, room temp., 1 h

9: 91 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.25 h / Heating

10: 76 percent / 1.) N-methyl-morpholine-N-oxide monohydrate, 4 Angstroem sieves / 2.) tetra-n-propylammonium perruthenate / CH₂Cl₂ / 1.) room temp., 10 min; 2.) 5 min

11: NaO₂Cl, 2-methyl-2-butene, KH₂PO₄ / 2-methyl-propan-2-ol; H₂O / Ambient temperature

With dmap; Oxone; sodium hydroxide; sodium chlorite; disodium hydrogenphosphate; potassium dihydrogenphosphate; n-butyllithium; sodium amalgam; 2-methyl-but-2-ene; dimethylsulfide borane complex; 4 A molecular sieve; tetrabutyl ammonium fluoride; dihydrogen peroxide; tert.-butyl lithium; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; tetrapropylammonium perruthennate; In tetrahydrofuran; diethyl ether; dichloromethane; water; tert-butyl alcohol; benzene;

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

Reference yield:

5-hydroxymethyl-4-methoxy-1-methyl-1,3-cyclohexadiene (127785-50-6) → (2R,6S,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 (124553-38-4)

Guidance literature:

Multi-step reaction with 20 steps

1: 98 percent / 4-dimethylaminopyridine, triethylamine / CH₂Cl₂ / 18 h / 0 °C

2: 88 percent / pyridinium-p-toluenesulphonate / benzene / 16 h / Heating; Dean-Stark conditions

3: 71 percent / osmium tetroxide, N-methylmorpholine-N-oxide monohydrate / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 2 h / Ambient temperature

4: 43 percent / 1.) triethylamine; 2.) 4-dimethylaminopyridine / CH₂Cl₂ / 3 h / 0 °C / 1.) 10 min

5: 88 percent / potassium carbonate / methanol / 1 h / Ambient temperature

6: 100 percent / pyridinium-p-toluenesulphonate / CH₂Cl₂ / 0.33 h / Ambient temperature

7: 94 percent / acetic anhydride / 1 h / Heating

8: 1.) BH₃*DMS; 2.) aq. NaOH, H₂O₂ / 1.) THF, 10 deg C, --> room temp., 16 h; 2.) H₂O, 0 deg C, 1 h

9: 98 percent / palladium(II) chloride-acetonitrile complex / acetone / 7 h / Ambient temperature

10: 87 percent / tert-butyl-lithium / diethyl ether; tetrahydrofuran / 1 h / -78 °C

11: 1.) mCPBA; 2.) oxone / 1.) CH₂Cl₂, 0 deg C, 10 min; 2.) methanol/THF/H₂O, 0 deg C, 5 h

12: 1.) BH₃*DMS; 2.) aq. NaOH, H₂O₂ / 1.) THF, 0 deg C, --> room temp., 16 h; 2.) H₂O, 30 min

13: 45 percent / pyridinium-p-toluene sulphonate / benzene / 1 h / Heating; Dean-Stark conditions

14: 1.) n-butyllithium / 1.) hexanes, THF, -78 deg C, 15 min; 2.) -78 deg C, 1 h

15: 99 percent / mCPBA, sat. sodium hydrogencarbonate / CH₂Cl₂ / 0.75 h / 10 °C

16: 84 percent / 1.) tert-butyllithium / tetrahydrofuran / 1 h / -78 °C / 1.) -78 deg C, 10 min

17: 1.) 6percentsodium amalgam, Na₂HPO₄; 2.) DMAP / 1.) THF/MeOH, -40 deg C, 70 min; 2.) CH₂Cl₂, pyridine, room temp., 1 h

18: 91 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.25 h / Heating

19: 76 percent / 1.) N-methyl-morpholine-N-oxide monohydrate, 4 Angstroem sieves / 2.) tetra-n-propylammonium perruthenate / CH₂Cl₂ / 1.) room temp., 10 min; 2.) 5 min

20: NaO₂Cl, 2-methyl-2-butene, KH₂PO₄ / 2-methyl-propan-2-ol; H₂O / Ambient temperature

With dmap; dichloro bis(acetonitrile) palladium(II); Oxone; sodium hydroxide; sodium chlorite; disodium hydrogenphosphate; potassium dihydrogenphosphate; osmium(VIII) oxide; n-butyllithium; sodium amalgam; 2-methyl-but-2-ene; dimethylsulfide borane complex; 4 A molecular sieve; tetrabutyl ammonium fluoride; dihydrogen peroxide; tert.-butyl lithium; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; tetrapropylammonium perruthennate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetic anhydride; acetone; tert-butyl alcohol; benzene;

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,6S,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 (124553-38-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 84 percent / 1.) tert-butyllithium / tetrahydrofuran / 1 h / -78 °C / 1.) -78 deg C, 10 min

2: 1.) 6percentsodium amalgam, Na₂HPO₄; 2.) DMAP / 1.) THF/MeOH, -40 deg C, 70 min; 2.) CH₂Cl₂, pyridine, room temp., 1 h

3: 91 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.25 h / Heating

4: 76 percent / 1.) N-methyl-morpholine-N-oxide monohydrate, 4 Angstroem sieves / 2.) tetra-n-propylammonium perruthenate / CH₂Cl₂ / 1.) room temp., 10 min; 2.) 5 min

5: NaO₂Cl, 2-methyl-2-butene, KH₂PO₄ / 2-methyl-propan-2-ol; H₂O / Ambient temperature

With dmap; sodium chlorite; disodium hydrogenphosphate; potassium dihydrogenphosphate; sodium amalgam; 2-methyl-but-2-ene; 4 A molecular sieve; tetrabutyl ammonium fluoride; tert.-butyl lithium; 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol;

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

upstream 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

(-)-(2S,4S,5S)-2-<(tert-butyldiphenylsilyloxy)methyl>-5-hydroxy-4-methylcyclohexanone

5-hydroxymethyl-4-methoxy-1-methyl-1,3-cyclohexadiene

5-<(tert-butyldiphenylsilyloxy)methyl>-4-methoxy-1-methyl-1,3-cyclohexadiene

Downstream raw materials:

(2R,6S,7R,9S,10S)-10-Hydroxy-5-[(2E,6E)-(R)-8-((2R,4S,6R,8R,9S)-4-hydroxy-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

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

(+)-5-O-desmethyl-3,4S-dihydromilbemycin β₁ 7,8'-R-benzylidene acetal

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