3-(tert-butyl-dimethyl-silanyloxy)-11-[10-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-8-methoxy-1,3,7,9-tetramethyl-6-oxo-decyl]-13,15,17-trimethoxy-6,12,16-trimethyl-10,23-dioxa-bicyclo[17.3.1]tricosa-5,7,21-trien-9-one

Base Information

• Chemical Name: 3-(tert-butyl-dimethyl-silanyloxy)-11-[10-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-8-methoxy-1,3,7,9-tetramethyl-6-oxo-decyl]-13,15,17-trimethoxy-6,12,16-trimethyl-10,23-dioxa-bicyclo[17.3.1]tricosa-5,7,21-trien-9-one
• CAS No.: 618116-94-2
• Molecular Formula: C₆₄H₁₀₄O₁₁Si₂
• Molecular Weight: 1105.69

Synonyms:3-(tert-butyl-dimethyl-silanyloxy)-11-[10-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-8-methoxy-1,3,7,9-tetramethyl-6-oxo-decyl]-13,15,17-trimethoxy-6,12,16-trimethyl-10,23-dioxa-bicyclo[17.3.1]tricosa-5,7,21-trien-9-one

Chemical Property of 3-(tert-butyl-dimethyl-silanyloxy)-11-[10-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-8-methoxy-1,3,7,9-tetramethyl-6-oxo-decyl]-13,15,17-trimethoxy-6,12,16-trimethyl-10,23-dioxa-bicyclo[17.3.1]tricosa-5,7,21-trien-9-one

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Technology Process of 3-(tert-butyl-dimethyl-silanyloxy)-11-[10-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-8-methoxy-1,3,7,9-tetramethyl-6-oxo-decyl]-13,15,17-trimethoxy-6,12,16-trimethyl-10,23-dioxa-bicyclo[17.3.1]tricosa-5,7,21-trien-9-one

There total 10 articles about 3-(tert-butyl-dimethyl-silanyloxy)-11-[10-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-8-methoxy-1,3,7,9-tetramethyl-6-oxo-decyl]-13,15,17-trimethoxy-6,12,16-trimethyl-10,23-dioxa-bicyclo[17.3.1]tricosa-5,7,21-trien-9-one 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: 78.0%

3-(tert-butyl-dimethyl-silanyloxy)-11-[10-(tert-butyl-diphenyl-silanyloxy)-2,6-dihydroxy-8-methoxy-1,3,7,9-tetramethyl-decyl]-13,15,17-trimethoxy-6,12,16-trimethyl-10,23-dioxa-bicyclo[17.3.1]tricosa-5,7,21-trien-9-one (618116-85-1) → 3-(tert-butyl-dimethyl-silanyloxy)-11-[10-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-8-methoxy-1,3,7,9-tetramethyl-6-oxo-decyl]-13,15,17-trimethoxy-6,12,16-trimethyl-10,23-dioxa-bicyclo[17.3.1]tricosa-5,7,21-trien-9-one (618116-94-2)

Guidance literature:

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/ol0352299

Reference yield:

methyl (E,E)-(7S)-8-[(2R,6S)-6-{(2S,3R)-2-methoxy-3-methylpentan-4-on-1-yl}-5,6-dihydro-2H-pyran-2-yl]-7-tert-butyldimethylsilyloxy-4-methylocta-2,4-dienoate (157830-71-2) → 3-(tert-butyl-dimethyl-silanyloxy)-11-[10-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-8-methoxy-1,3,7,9-tetramethyl-6-oxo-decyl]-13,15,17-trimethoxy-6,12,16-trimethyl-10,23-dioxa-bicyclo[17.3.1]tricosa-5,7,21-trien-9-one (618116-94-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 94 percent / Et₃N; LHDMS / tetrahydrofuran / 1.33 h / -78 °C

2: 87 percent / BF₃*OEt₃ / CH₂Cl₂ / 1.33 h / -78 °C

3: 77 percent / catecholborane / tetrahydrofuran / 26 h / -78 - -20 °C

4: 99 percent / 2,6-di-tert-butylpyridine / 8.5 h / 20 °C

5: 97 percent / NaBH₄ / methanol / 3 h / -20 - 0 °C

6: 79 percent / FeCl₃*SiO₂ / CHCl₃ / 8 h / 20 °C

7: 93 percent / Ba(OH)2 / methanol / 18 h / 40 °C

8: 52 percent / Et₃N; 2,4,6-trichlorobenzoyl chloride; 4-DMAP / toluene / 13 h / 20 °C

9: 40 percent / Ti(OPr-i)4 / CH₂Cl₂ / 84 h / 20 °C

10: 78 percent / molecular sieves 4 Angstroem; NMO; TPAP / CH₂Cl₂ / 2 h / 20 °C

With titanium(IV) isopropylate; dmap; barium dihydroxide; sodium tetrahydroborate; N-methyl-2-indolinone; 2,6-di-tert-butyl-pyridine; tetrapropylammonium perruthennate; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; boron trifluoride diethyl etherate; silica gel; iron(III) chloride; triethylamine; lithium hexamethyldisilazane; benzo[1,3,2]dioxaborole; In tetrahydrofuran; methanol; dichloromethane; chloroform; toluene;

DOI:10.1021/ol0352299

Reference yield:

(2E,4E)-(S)-7-(tert-Butyl-dimethyl-silanyloxy)-8-[(2R,6S)-6-((2S,3R)-2-methoxy-3-methyl-4-trimethylsilanyloxy-pent-4-enyl)-5,6-dihydro-2H-pyran-2-yl]-4-methyl-octa-2,4-dienoic acid methyl ester (157830-72-3) → 3-(tert-butyl-dimethyl-silanyloxy)-11-[10-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-8-methoxy-1,3,7,9-tetramethyl-6-oxo-decyl]-13,15,17-trimethoxy-6,12,16-trimethyl-10,23-dioxa-bicyclo[17.3.1]tricosa-5,7,21-trien-9-one (618116-94-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 87 percent / BF₃*OEt₃ / CH₂Cl₂ / 1.33 h / -78 °C

2: 77 percent / catecholborane / tetrahydrofuran / 26 h / -78 - -20 °C

3: 99 percent / 2,6-di-tert-butylpyridine / 8.5 h / 20 °C

4: 97 percent / NaBH₄ / methanol / 3 h / -20 - 0 °C

5: 79 percent / FeCl₃*SiO₂ / CHCl₃ / 8 h / 20 °C

6: 93 percent / Ba(OH)2 / methanol / 18 h / 40 °C

7: 52 percent / Et₃N; 2,4,6-trichlorobenzoyl chloride; 4-DMAP / toluene / 13 h / 20 °C

8: 40 percent / Ti(OPr-i)4 / CH₂Cl₂ / 84 h / 20 °C

9: 78 percent / molecular sieves 4 Angstroem; NMO; TPAP / CH₂Cl₂ / 2 h / 20 °C

With titanium(IV) isopropylate; dmap; barium dihydroxide; sodium tetrahydroborate; N-methyl-2-indolinone; 2,6-di-tert-butyl-pyridine; tetrapropylammonium perruthennate; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; boron trifluoride diethyl etherate; silica gel; iron(III) chloride; triethylamine; benzo[1,3,2]dioxaborole; In tetrahydrofuran; methanol; dichloromethane; chloroform; toluene;

DOI:10.1021/ol0352299

upstream raw materials:

3-(tert-butyl-dimethyl-silanyloxy)-11-[10-(tert-butyl-diphenyl-silanyloxy)-2,6-dihydroxy-8-methoxy-1,3,7,9-tetramethyl-decyl]-13,15,17-trimethoxy-6,12,16-trimethyl-10,23-dioxa-bicyclo[17.3.1]tricosa-5,7,21-trien-9-one

methyl (E,E)-(7S)-8-[(2R,6S)-6-{(2S,3R)-2-methoxy-3-methylpentan-4-on-1-yl}-5,6-dihydro-2H-pyran-2-yl]-7-tert-butyldimethylsilyloxy-4-methylocta-2,4-dienoate

(2E,4E)-(S)-7-(tert-Butyl-dimethyl-silanyloxy)-8-[(2R,6S)-6-((2S,3R)-2-methoxy-3-methyl-4-trimethylsilanyloxy-pent-4-enyl)-5,6-dihydro-2H-pyran-2-yl]-4-methyl-octa-2,4-dienoic acid methyl ester

3-(tert-butyl-dimethyl-silanyloxy)-11-[8-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-6-methoxy-1,5,7-trimethyl-octyl]-13-hydroxy-15,17,19-trimethoxy-6,12,14,18-tetramethyl-10,25-dioxa-bicyclo[19.3.1]pentacosa-5,7,23-trien-9-one

Downstream raw materials:

3-(tert-butyl-dimethyl-silanyloxy)-11-[10-(tert-butyl-diphenyl-silanyloxy)-8-methoxy-1,3,7,9-tetramethyl-6-oxo-2-triethylsilanyloxy-decyl]-13,15,17-trimethoxy-6,12,16-trimethyl-10,23-dioxa-bicyclo[17.3.1]tricosa-5,7,21-trien-9-one

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