(4R,9R,10R,12R)-9-(tert-butyl-dimethylsilanyloxy)-4,12,14,14-tetramethoxy-10-(4-methoxybenzyloxy)-7-methyl-1-(trimethylsilanyl)-tetradeca-di-(5E,7E)-en-1-yne

Base Information

• Chemical Name: (4R,9R,10R,12R)-9-(tert-butyl-dimethylsilanyloxy)-4,12,14,14-tetramethoxy-10-(4-methoxybenzyloxy)-7-methyl-1-(trimethylsilanyl)-tetradeca-di-(5E,7E)-en-1-yne
• CAS No.: 213978-56-4
• Molecular Formula: C₃₆H₆₂O₇Si₂
• Molecular Weight: 663.055
• Mol file: 213978-56-4.mol

Synonyms:(4R,9R,10R,12R)-9-(tert-butyl-dimethylsilanyloxy)-4,12,14,14-tetramethoxy-10-(4-methoxybenzyloxy)-7-methyl-1-(trimethylsilanyl)-tetradeca-di-(5E,7E)-en-1-yne

Chemical Property of (4R,9R,10R,12R)-9-(tert-butyl-dimethylsilanyloxy)-4,12,14,14-tetramethoxy-10-(4-methoxybenzyloxy)-7-methyl-1-(trimethylsilanyl)-tetradeca-di-(5E,7E)-en-1-yne

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,9R,10R,12R)-9-(tert-butyl-dimethylsilanyloxy)-4,12,14,14-tetramethoxy-10-(4-methoxybenzyloxy)-7-methyl-1-(trimethylsilanyl)-tetradeca-di-(5E,7E)-en-1-yne

There total 29 articles about (4R,9R,10R,12R)-9-(tert-butyl-dimethylsilanyloxy)-4,12,14,14-tetramethoxy-10-(4-methoxybenzyloxy)-7-methyl-1-(trimethylsilanyl)-tetradeca-di-(5E,7E)-en-1-yne 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: 74.0%

(2R)-2'-[2-methoxy-5-(trimethylsilanyl)-pent-4-yn-1-ylsulfonyl]-benzothiazole (213978-43-9) + (4R,5R,7R)-4-(tert-butyl-dimethyl-silanyloxy)-7,9,9-trimethoxy-5-(4'-methoxy-benzyloxy)-2-methyl-non-(2E)-enal (213978-44-0) → (4R,9R,10R,12R)-9-(tert-butyl-dimethylsilanyloxy)-4,12,14,14-tetramethoxy-10-(4-methoxybenzyloxy)-7-methyl-1-(trimethylsilanyl)-tetradeca-di-(5E,7E)-en-1-yne (213978-56-4)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(98)01258-1

Reference yield: 74.0%

(2R)-2'-[2-methoxy-5-(trimethylsilanyl)-pent-4-yn-1-ylsulfonyl]-benzothiazole (213978-43-9) + (4R,5R,7R)-4-(tert-butyl-dimethyl-silanyloxy)-7,9,9-trimethoxy-5-(4'-methoxy-benzyloxy)-2-methyl-non-(2E)-enal (213978-44-0) → (4R,9R,10R,12R)-9-(tert-butyl-dimethylsilanyloxy)-4,12,14,14-tetramethoxy-10-(4-methoxybenzyloxy)-7-methyl-1-(trimethylsilanyl)-tetradeca-di-(5E,7E)-en-1-yne (213978-56-4) + (4R,9R,10R,12R)-9-(tert-butyl-dimethylsilanyloxy)-4,12,14,14-tetramethoxy-10-(4-methoxybenzyloxy)-7-methyl-1-(trimethylsilanyl)-tetradeca-di-(5Z,7E)-en-1-yne

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 - 20 ℃; for 4h;

DOI:10.1039/b308305e

Reference yield:

2-deoxy-4,5-O-isopropylidene-D-threo-pentose diethyl dithioacetal (67320-20-1) → (4R,9R,10R,12R)-9-(tert-butyl-dimethylsilanyloxy)-4,12,14,14-tetramethoxy-10-(4-methoxybenzyloxy)-7-methyl-1-(trimethylsilanyl)-tetradeca-di-(5E,7E)-en-1-yne (213978-56-4)

Guidance literature:

Multi-step reaction with 14 steps

1.1: t-BuOK / tetrahydrofuran / 1 h / -20 °C

1.2: 98 percent / NBu₄I / tetrahydrofuran / 15 h / 20 °C

2.1: 91 percent / aq. CaCO₃; Hg(ClO₄)2 / tetrahydrofuran / 3 h / 20 °C

3.1: diethyl ether / 3 h / -78 °C

3.2: 4.69 g / aq. NaOH; H₂O₂ / diethyl ether / 2 h / Heating

4.1: t-BuOK / tetrahydrofuran / 0.5 h / -20 °C

4.2: 97 percent / tetrahydrofuran / 6 h / 20 °C

5.1: 88 percent / 10-camphorsulfonic acid / methanol / 6 h / 0 - 20 °C

6.1: 98 percent / Et₃N / CH₂Cl₂ / 1 h / 0 - 20 °C

7.1: NMO; aq. OsO₄ / acetone / 12 h / 20 °C

8.1: 6.2 g / aq. NaIO₄; silica / petroleum ether; CH₂Cl₂ / 3 h / 20 °C

9.1: 89 percent / 10-camphorsulfonic acid / CH₂Cl₂ / 1 h / 20 °C

10.1: 95 percent / 2,6-di-tert-butylpyridine; Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

11.1: 94 percent / benzene / 48 h / Heating

12.1: 89 percent / DIBALH / CH₂Cl₂; hexane / 3 h / -78 - 20 °C

13.1: 94 percent / 2,6-lutidine; Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

14.1: 74 percent / NaHMDS / tetrahydrofuran / 4 h / -78 - 20 °C

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; 2,6-di-tert-butyl-pyridine; mercury(II) perchlorate; (1S)-10-camphorsulfonic acid; potassium tert-butylate; sodium hexamethyldisilazane; silica gel; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; calcium carbonate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetone; Petroleum ether; benzene; 11.1: Wittig reaction;

DOI:10.1039/b308305e

upstream raw materials:

(2R)-2'-[2-methoxy-5-(trimethylsilanyl)-pent-4-yn-1-ylsulfonyl]-benzothiazole

(4R,5R,7R)-4-(tert-butyl-dimethyl-silanyloxy)-7,9,9-trimethoxy-5-(4'-methoxy-benzyloxy)-2-methyl-non-(2E)-enal

D-xylose

D-xylose diethyl dithioacetal

Downstream raw materials:

(5R,7R,8R,13R)-8-(tert-butyl-dimethylsilanyloxy)-5,13-dimethoxy-7-(4-methoxybenzyloxy)-10-methyl-3-oxo-16-(trimethylsilanyl)-hexadeca-di-(9E,11E)-en-15-ynoic acid ethyl ester

(3R,5R,6R,11R)-6-(tert-butyl-dimethylsilanyloxy)-3,11-dimethoxy-5-(4-methoxybenzyloxy)-8-methyl-14-(trimethylsilanyl)-tetradeca-7,9-di-(7E,9E)-en-13-ynal

Refernces

• 1、 Pattenden, Gerald,Plowright, Alleyn T.,Tornos, James A.,Ye, Tao. "Synthetic studies towards phorboxazole A. A convergent synthesis of the C31-C46 polyene oxane-hemiacetal side chain". . p. 6099 - 6102. Retrieved 2007/10/03.