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

Base Information

Chemical Name: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
CAS No.:618116-86-2
Molecular Formula:C₆₄H₁₀₆O₁₁Si₂
Molecular Weight:1107.71
Hs Code.:

3-(<i>tert</i>-butyl-dimethyl-silanyloxy)-11-[8-(<i>tert</i>-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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 8 articles about 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 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: 34.0%

: 618116-84-0
7-(tert-butyl-dimethyl-silanyloxy)-8-{6-[18-(tert-butyl-diphenyl-silanyloxy)-8,10,14-trihydroxy-2,4,6,16-tetramethoxy-3,7,9,11,15,17-hexamethyl-octadecyl]-5,6-dihydro-2H-pyran-2-yl}-4-methyl-octa-2,4-dienoic acid

: 618116-86-2
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

: 618116-85-1
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

Guidance literature:: With dmap; 2,4,6-trichlorobenzoyl chloride; triethylamine; In toluene; at 20 ℃; for 13h;
DOI:10.1021/ol0352299

Reference yield:

: 157830-71-2
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

: 618116-86-2
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

Guidance literature:: Multi-step reaction with 8 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

With dmap; barium dihydroxide; sodium tetrahydroborate; 2,6-di-tert-butyl-pyridine; 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:

: 157830-72-3
(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

: 618116-86-2
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

Guidance literature:: Multi-step reaction with 7 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

With dmap; barium dihydroxide; sodium tetrahydroborate; 2,6-di-tert-butyl-pyridine; 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