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

Base Information

• Chemical Name: 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
• CAS No.: 618116-85-1
• Molecular Formula: C₆₄H₁₀₆O₁₁Si₂
• Molecular Weight: 1107.71
• Mol file: 618116-85-1.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 10 articles about 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 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: 40.0%

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 (618116-86-2) → 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)

Guidance literature:

With titanium(IV) isopropylate; In dichloromethane; at 20 ℃; for 84h;

DOI:10.1021/ol0352299

Reference yield: 34.0%

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 (618116-84-0) → 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 (618116-86-2) + 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)

Guidance literature:

With dmap; 2,4,6-trichlorobenzoyl chloride; triethylamine; In toluene; at 20 ℃; for 13h;

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)-2,6-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)

Guidance literature:

Multi-step reaction with 9 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

With titanium(IV) isopropylate; 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

upstream raw materials:

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

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

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

Downstream raw materials:

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

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