(11E)(4S,7S,9S,3R,6R,8R)-8-methoxy-3-{[(4-methoxyphenyl)methoxy]methyl}-7,9-dimethyltridec-11-ene-4,6-diol

Base Information

• Chemical Name: (11E)(4S,7S,9S,3R,6R,8R)-8-methoxy-3-{[(4-methoxyphenyl)methoxy]methyl}-7,9-dimethyltridec-11-ene-4,6-diol
• CAS No.: 332842-86-1
• Molecular Formula: C₂₅H₄₂O₅
• Molecular Weight: 422.605
• Mol file: 332842-86-1.mol

Synonyms:(11E)(4S,7S,9S,3R,6R,8R)-8-methoxy-3-{[(4-methoxyphenyl)methoxy]methyl}-7,9-dimethyltridec-11-ene-4,6-diol

Chemical Property of (11E)(4S,7S,9S,3R,6R,8R)-8-methoxy-3-{[(4-methoxyphenyl)methoxy]methyl}-7,9-dimethyltridec-11-ene-4,6-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (11E)(4S,7S,9S,3R,6R,8R)-8-methoxy-3-{[(4-methoxyphenyl)methoxy]methyl}-7,9-dimethyltridec-11-ene-4,6-diol

There total 15 articles about (11E)(4S,7S,9S,3R,6R,8R)-8-methoxy-3-{[(4-methoxyphenyl)methoxy]methyl}-7,9-dimethyltridec-11-ene-4,6-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:

(11E)(3S,6S,8S,7R,9R)-6-hydroxy-8-methoxy-3-{[(4-methoxyphenyl)methoxy]methyl}-7,9-dimethyltridec-11-en-4-one (332842-80-5) → (11E)(4S,7S,9S,3R,6R,8R)-8-methoxy-3-{[(4-methoxyphenyl)methoxy]methyl}-7,9-dimethyltridec-11-ene-4,6-diol (332842-86-1) + (11E)(7S,9S,3R,4R,6R,8R)-8-methoxy-3-{[(4-methoxyphenyl)methoxy]methyl}-7,9-dimethyltridec-11-ene-4,6-diol (332842-81-6)

Guidance literature:

With samarium diiodide; In tetrahydrofuran; methanol; at -16 ℃; for 14h;

DOI:10.1021/ol015531m

Reference yield:

p-Methoxybenzyl bromide (2746-25-0) → (11E)(4S,7S,9S,3R,6R,8R)-8-methoxy-3-{[(4-methoxyphenyl)methoxy]methyl}-7,9-dimethyltridec-11-ene-4,6-diol (332842-86-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: KH / various solvents / 5 h / -15 - 20 °C

2.1: 0.85 g / OsO₄; NaIO₄; NMO / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 5 h / 20 °C

3.1: LiHMDS / tetrahydrofuran; hexane / 0.25 h / -78 °C

3.2: tetrahydrofuran; hexane / 15 h / -78 °C

4.1: 398 mg / BF₃*Et₂O / CH₂Cl₂ / 1 h / -90 °C

5.1: 16 mg / SmI₂ / tetrahydrofuran; methanol / 14 h / -16 °C

With sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; samarium diiodide; boron trifluoride diethyl etherate; potassium hydride; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; hexane; dichloromethane; various solvents; water; tert-butyl alcohol;

DOI:10.1021/ol015531m

Reference yield:

1-benzyloxy-2(S),4(S)-dimethyl-hex-5-en-3(R)-ol (106357-30-6) → (11E)(4S,7S,9S,3R,6R,8R)-8-methoxy-3-{[(4-methoxyphenyl)methoxy]methyl}-7,9-dimethyltridec-11-ene-4,6-diol (332842-86-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: KH / tetrahydrofuran / 0.5 h / -5 °C

1.2: 92 percent / tetrahydrofuran / 2.5 h / 20 °C

2.1: 9-BBN / tetrahydrofuran / 6 h / sonication

2.2: 88 percent / H₂O₂ / methanol; tetrahydrofuran; various solvent(s)

3.1: TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 1.5 h / 0 °C

4.1: 1.6 g / PPh₃ / CH₂Cl₂ / 0.5 h / -78 °C

5.1: n-BuLi / tetrahydrofuran; various solvent(s) / 1 h / -78 °C

5.2: 99 percent / DMPU / tetrahydrofuran; various solvent(s) / 1 h

6.1: 84 percent / Li; NH₃ / tetrahydrofuran / 3.33 h / -78 - -40 °C

7.1: TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.5 h / 0 °C

8.1: 398 mg / BF₃*Et₂O / CH₂Cl₂ / 1 h / -90 °C

9.1: 16 mg / SmI₂ / tetrahydrofuran; methanol / 14 h / -16 °C

With 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; N-methyl-2-indolinone; samarium diiodide; tetrapropylammonium perruthennate; 4 A molecular sieve; boron trifluoride diethyl etherate; ammonia; lithium; potassium hydride; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ol015531m

upstream raw materials:

(11E)(3S,6S,8S,7R,9R)-6-hydroxy-8-methoxy-3-{[(4-methoxyphenyl)methoxy]methyl}-7,9-dimethyltridec-11-en-4-one

p-Methoxybenzyl bromide

1-benzyloxy-2(S),4(S)-dimethyl-hex-5-en-3(R)-ol

(E)-(2R,3R,4S)-3-Methoxy-2,4-dimethyl-oct-6-enal