(2S,3R,4S,5Z,8S,9R,10S,11S,12S,13Z)-1,11-bis-(p-methoxybenzyloxy)-2,4,6,8,10,12-hexamethyl-hexadeca-5,13,15-triene-3,9-diol

Base Information

• Chemical Name: (2S,3R,4S,5Z,8S,9R,10S,11S,12S,13Z)-1,11-bis-(p-methoxybenzyloxy)-2,4,6,8,10,12-hexamethyl-hexadeca-5,13,15-triene-3,9-diol
• CAS No.: 373645-72-8
• Molecular Formula: C₃₈H₅₆O₆
• Molecular Weight: 608.859
• Mol file: 373645-72-8.mol

Synonyms:(2S,3R,4S,5Z,8S,9R,10S,11S,12S,13Z)-1,11-bis-(p-methoxybenzyloxy)-2,4,6,8,10,12-hexamethyl-hexadeca-5,13,15-triene-3,9-diol

Chemical Property of (2S,3R,4S,5Z,8S,9R,10S,11S,12S,13Z)-1,11-bis-(p-methoxybenzyloxy)-2,4,6,8,10,12-hexamethyl-hexadeca-5,13,15-triene-3,9-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S,5Z,8S,9R,10S,11S,12S,13Z)-1,11-bis-(p-methoxybenzyloxy)-2,4,6,8,10,12-hexamethyl-hexadeca-5,13,15-triene-3,9-diol

There total 23 articles about (2S,3R,4S,5Z,8S,9R,10S,11S,12S,13Z)-1,11-bis-(p-methoxybenzyloxy)-2,4,6,8,10,12-hexamethyl-hexadeca-5,13,15-triene-3,9-diol 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: 96.0%

(2S,3R,4S,5Z,8R,9S,10R,11S,12S,13Z)-1,11-bis-(p-methoxybenzyloxy)-8-[(2,4,6-trimethylphenyl)sulfonyloxymethyl]-2,4,6,10,12-pentamethyl-hexadeca-5,13,15-trien-3,9-diol (373645-71-7) → (2S,3R,4S,5Z,8S,9R,10S,11S,12S,13Z)-1,11-bis-(p-methoxybenzyloxy)-2,4,6,8,10,12-hexamethyl-hexadeca-5,13,15-triene-3,9-diol (373645-72-8)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at -78 - 0 ℃; for 1.5h;

DOI:10.1021/ja011211m

Reference yield:

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) → (2S,3R,4S,5Z,8S,9R,10S,11S,12S,13Z)-1,11-bis-(p-methoxybenzyloxy)-2,4,6,8,10,12-hexamethyl-hexadeca-5,13,15-triene-3,9-diol (373645-72-8)

Guidance literature:

Multi-step reaction with 14 steps

1.1: triflic acid / diethyl ether / 2 h / 20 °C

2.1: 85 percent / i-PrMgCl / tetrahydrofuran / 0.5 h / -15 °C

3.1: 90 percent / tetrahydrofuran; diethyl ether / 2 h / 0 °C

4.1: Et₃N / diethyl ether / 1 h / 0 °C

5.1: diethyl ether / 21 h / -20 °C

5.2: 95 percent / 30percent aq. H₂O₂ / methanol / 0 - 20 °C / pH 7

6.1: 96 percent / SmI₂ / tetrahydrofuran / 1.5 h / -10 °C

7.1: 97 percent / K₂CO₃ / methanol; H₂O / 5 h / 20 °C

8.1: 94 percent / PPTS / toluene / 4 h / Heating

9.1: NaIO₄; NaHCO₃ / methanol; H₂O / 2 h / 20 °C

10.1: 82 percent / DBU; 1-(t-butyldimethylsiloxy)-1-methoxyethene / various solvent(s) / 8 h / Heating

11.1: LiTMP; LiBr / tetrahydrofuran / 0.5 h / -100 °C

11.2: 39 percent / tetrahydrofuran / 0.17 h / -100 °C

12.1: 74 percent / LiAlH₄ / tetrahydrofuran / 3 h / -78 - -15 °C

13.1: 73 percent / Et₃N / CH₂Cl₂ / 40 h / 20 °C

14.1: 96 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / -78 - 0 °C

With sodium periodate; lithium aluminium tetrahydride; samarium diiodide; trifluorormethanesulfonic acid; 2,2,6,6-tetramethylpiperidinyl-lithium; isopropylmagnesium chloride; ketene t-butyldimethylsilyl methyl acetal; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium bromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; 6.1: Evans-Tischenko reaction / 10.1: Claisen rearrangement;

DOI:10.1021/ja011211m

Reference yield:

(5S,6R,7S)-8-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7-dimethyl-3-trimethylsilanyl-oct-1-en-4-ol → (2S,3R,4S,5Z,8S,9R,10S,11S,12S,13Z)-1,11-bis-(p-methoxybenzyloxy)-2,4,6,8,10,12-hexamethyl-hexadeca-5,13,15-triene-3,9-diol (373645-72-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 98 percent / KH / tetrahydrofuran / 2 h / 0 - 20 °C

2.1: 92 percent / CSA / methanol; CH₂Cl₂ / 1 h / 20 °C

3.1: 91 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

4.1: LiTMP; LiBr / tetrahydrofuran / 0.5 h / -100 °C

4.2: 39 percent / tetrahydrofuran / 0.17 h / -100 °C

5.1: 74 percent / LiAlH₄ / tetrahydrofuran / 3 h / -78 - -15 °C

6.1: 73 percent / Et₃N / CH₂Cl₂ / 40 h / 20 °C

7.1: 96 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / -78 - 0 °C

With lithium aluminium tetrahydride; camphor-10-sulfonic acid; 2,2,6,6-tetramethylpiperidinyl-lithium; potassium hydride; Dess-Martin periodane; triethylamine; lithium bromide; In tetrahydrofuran; methanol; dichloromethane; 1.1: Peterson elimination;

DOI:10.1021/ja011211m

upstream raw materials:

(2S,3R,4S,5Z,8R,9S,10R,11S,12S,13Z)-1,11-bis-(p-methoxybenzyloxy)-8-[(2,4,6-trimethylphenyl)sulfonyloxymethyl]-2,4,6,10,12-pentamethyl-hexadeca-5,13,15-trien-3,9-diol

O-(4-methoxybenzyl)-trichloroacetimidate

methyl (2S)-[(4-methoxybenzyl)oxy]-2-methylpropanoate

(+)-(Z)-(2S,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethylocta-5,7-dien-1-ol

Downstream raw materials:

1-[(5Z,13Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-11-(4-methoxybenzoxy)-3,9-bis(tert-butyldimethylsilanyloxy)-2,4,6,8,10,12-hexamethylhexadeca-5,13,15-trienyloxymethyl]-4-methoxybenzene