(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

Base Information

• Chemical Name: (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
• CAS No.: 213978-71-3
• Molecular Formula: C₃₄H₅₆O₆Si₂
• Molecular Weight: 616.986
• Mol file: 213978-71-3.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 30 articles about (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 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: 95.0%

(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) → (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 (213978-71-3)

Guidance literature:

With dimethylboron bromide; at -78 ℃;

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

Reference yield:

2-deoxy-4,5-O-isopropylidene-D-threo-pentose diethyl dithioacetal (67320-20-1) → (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 (213978-71-3)

Guidance literature:

Multi-step reaction with 15 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

15.1: 95 percent / Me₂BBr / CH₂Cl₂; diethyl ether / 2.5 h / -78 °C

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; 2,6-di-tert-butyl-pyridine; mercury(II) perchlorate; dimethylboron bromide; (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

Reference yield:

(2R)-2-methoxy-pent-4-yn-1-ol (213979-57-8) → (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 (213978-71-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 1 h / -78 °C

1.2: 70 percent / hexane; tetrahydrofuran / 2 h / -78 - 20 °C

2.1: 94 percent / PPh₃; DEAD / tetrahydrofuran / 1.5 h / 0 °C

3.1: 85 percent / MCPBA; NaHCO₃ / CH₂Cl₂ / 15 h / 20 °C

4.1: 74 percent / NaHMDS / tetrahydrofuran / 4 h / -78 - 20 °C

5.1: 95 percent / Me₂BBr / CH₂Cl₂; diethyl ether / 2.5 h / -78 °C

With n-butyllithium; dimethylboron bromide; sodium hexamethyldisilazane; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;

DOI:10.1039/b308305e

upstream raw materials:

(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

D-xylose

D-xylose diethyl dithioacetal

2-deoxy-4,5-O-isopropylidene-D-threo-pentose 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

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.