(3R,4S,5S,6R)-4-[(E)-1,5-dimethyl-hex-1,4-dienyl]-5-hydroxy-6-p-methoxybenzyloxy-1-oxaspiro[2.5]octane

Base Information

• Chemical Name: (3R,4S,5S,6R)-4-[(E)-1,5-dimethyl-hex-1,4-dienyl]-5-hydroxy-6-p-methoxybenzyloxy-1-oxaspiro[2.5]octane
• CAS No.: 364337-28-0
• Molecular Formula: C₂₃H₃₂O₄
• Molecular Weight: 372.505
• Mol file: 364337-28-0.mol

Synonyms:(3R,4S,5S,6R)-4-[(E)-1,5-dimethyl-hex-1,4-dienyl]-5-hydroxy-6-p-methoxybenzyloxy-1-oxaspiro[2.5]octane

Chemical Property of (3R,4S,5S,6R)-4-[(E)-1,5-dimethyl-hex-1,4-dienyl]-5-hydroxy-6-p-methoxybenzyloxy-1-oxaspiro[2.5]octane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S,5S,6R)-4-[(E)-1,5-dimethyl-hex-1,4-dienyl]-5-hydroxy-6-p-methoxybenzyloxy-1-oxaspiro[2.5]octane

There total 15 articles about (3R,4S,5S,6R)-4-[(E)-1,5-dimethyl-hex-1,4-dienyl]-5-hydroxy-6-p-methoxybenzyloxy-1-oxaspiro[2.5]octane 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: 75.0%

(3R,4S,5S,6R)-4-[(E)-1,5-dimethyl-hex-1,4-dienyl]-6-p-methoxybenzyloxy-5-trimethylsilyloxy-1-oxaspiro[2.5]octane (364337-27-9) → (3R,4S,5S,6R)-4-[(E)-1,5-dimethyl-hex-1,4-dienyl]-5-hydroxy-6-p-methoxybenzyloxy-1-oxaspiro[2.5]octane (364337-28-0)

Guidance literature:

With water; toluene-4-sulfonic acid; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1021/ol016343z

Reference yield:

2,6-dimethyl-2,5-octadien-8-ol (16750-94-0) → (3R,4S,5S,6R)-4-[(E)-1,5-dimethyl-hex-1,4-dienyl]-5-hydroxy-6-p-methoxybenzyloxy-1-oxaspiro[2.5]octane (364337-28-0)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 35 percent / CrO₃; sulfuric acid / H₂O; acetone / 0.25 h / 0 °C

2.1: triethylamine / tetrahydrofuran / 0.5 h / -78 - 0 °C

3.1: 188 mg / tetrahydrofuran; hexane / 0.33 h / -78 °C

4.1: LDA / tetrahydrofuran; hexane / 0.75 h / -78 °C

4.2: tetrahydrofuran; hexane / 0.75 h / -78 °C

5.1: 4.61 g / tetrabutylammonium periodate / CHCl₃ / 2 h / 60 °C

6.1: trimethylaluminium / toluene; tetrahydrofuran / 0.75 h / 20 °C

6.2: 71 percent / toluene; tetrahydrofuran / 0 °C

7.1: 100 percent / triethylamine; DMAP / tetrahydrofuran / 2 h / 20 °C

8.1: 87 percent / tetrahydrofuran / 12 h / 20 °C

9.1: Ti(O-i-Pr)4 / CH₂Cl₂ / 0.5 h / 30 °C

9.2: 53 percent / Grubb's complex "type 1" / CH₂Cl₂ / 24 h / 55 °C

10.1: 83 percent / H₂ / Raney Ni / tetrahydrofuran; H₂O / 1 h / 0 °C

11.1: NaH / dimethylsulfoxide; tetrahydrofuran / 1 h / 20 °C

11.2: LiI / dimethylsulfoxide; tetrahydrofuran / 0.67 h / 20 °C

11.3: 53 percent / dimethylsulfoxide; tetrahydrofuran / 0.5 h / 20 °C

12.1: 75 percent / p-toluenesulfonic acid; water / tetrahydrofuran / 0.5 h / 20 °C

With chromium(VI) oxide; titanium(IV) isopropylate; dmap; sulfuric acid; water; hydrogen; trimethylaluminum; sodium hydride; tetrabutylammonium periodite; toluene-4-sulfonic acid; triethylamine; lithium diisopropyl amide; nickel; In tetrahydrofuran; hexane; dichloromethane; chloroform; water; dimethyl sulfoxide; acetone; toluene;

DOI:10.1021/ol016343z

Reference yield:

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) → (3R,4S,5S,6R)-4-[(E)-1,5-dimethyl-hex-1,4-dienyl]-5-hydroxy-6-p-methoxybenzyloxy-1-oxaspiro[2.5]octane (364337-28-0)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 70 percent / camphorsulfonic acid / CH₂Cl₂ / 24 h / 20 °C

2.1: 94 percent / DIBAH / toluene / 0.33 h / -78 °C

3.1: LDA / tetrahydrofuran; hexane / 0.75 h / -78 °C

3.2: tetrahydrofuran; hexane / 0.75 h / -78 °C

4.1: 4.61 g / tetrabutylammonium periodate / CHCl₃ / 2 h / 60 °C

5.1: trimethylaluminium / toluene; tetrahydrofuran / 0.75 h / 20 °C

5.2: 71 percent / toluene; tetrahydrofuran / 0 °C

6.1: 100 percent / triethylamine; DMAP / tetrahydrofuran / 2 h / 20 °C

7.1: 87 percent / tetrahydrofuran / 12 h / 20 °C

8.1: Ti(O-i-Pr)4 / CH₂Cl₂ / 0.5 h / 30 °C

8.2: 53 percent / Grubb's complex "type 1" / CH₂Cl₂ / 24 h / 55 °C

9.1: 83 percent / H₂ / Raney Ni / tetrahydrofuran; H₂O / 1 h / 0 °C

10.1: NaH / dimethylsulfoxide; tetrahydrofuran / 1 h / 20 °C

10.2: LiI / dimethylsulfoxide; tetrahydrofuran / 0.67 h / 20 °C

10.3: 53 percent / dimethylsulfoxide; tetrahydrofuran / 0.5 h / 20 °C

11.1: 75 percent / p-toluenesulfonic acid; water / tetrahydrofuran / 0.5 h / 20 °C

With titanium(IV) isopropylate; dmap; camphor-10-sulfonic acid; water; hydrogen; trimethylaluminum; sodium hydride; diisobutylaluminium hydride; tetrabutylammonium periodite; toluene-4-sulfonic acid; triethylamine; lithium diisopropyl amide; nickel; In tetrahydrofuran; hexane; dichloromethane; chloroform; water; dimethyl sulfoxide; toluene;

DOI:10.1021/ol016343z

upstream raw materials:

(3R,4S,5S,6R)-4-[(E)-1,5-dimethyl-hex-1,4-dienyl]-6-p-methoxybenzyloxy-5-trimethylsilyloxy-1-oxaspiro[2.5]octane

2,6-dimethyl-2,5-octadien-8-ol

O-(4-methoxybenzyl)-trichloroacetimidate

(3E)-3,7-dimethyl-octa-3,6-dienoic acid