Cinnamonol

Base Information

• Chemical Name: Cinnamonol
• CAS No.: 58262-61-6
• Mol file: 58262-61-6.mol

Synonyms:

Chemical Property of Cinnamonol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Cinnamonol

There total 22 articles about Cinnamonol 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: 82.0%

(2S,3R,4R)-4-[(S)-(methoxymethoxy)(3,4-methylenedioxyphenyl)methyl]-2-(3,4-methylenedioxyphenyl)-3-tetrahydrofurancarbaldehyde (572916-32-6) → (1R,2S,5S,6S)-4-hydroxy-2,6-bis(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo[3.3.0]octane (58262-61-6,61254-18-0,63427-86-1)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 20 ℃; for 5h;

DOI:10.1271/bbb.67.838

Reference yield:

piperonal (120-57-0,30024-74-9) → (1R,2S,5S,6S)-4-hydroxy-2,6-bis(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo[3.3.0]octane (58262-61-6,61254-18-0,63427-86-1)

Guidance literature:

Multi-step reaction with 12 steps

1.1: LDA / tetrahydrofuran / 30 h / -75 °C

1.2: 43 percent / tetrahydrofuran / 1 h / -75 °C

2.1: 85 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

3.1: LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

4.1: 7.68 g / HCO₂H / diethyl ether / 0.17 h / -10 °C

5.1: NaIO₄ / methanol / 2 h / 20 °C

5.2: 71 percent / Ag₂CO₃*celite / toluene / 1 h / Heating

6.1: KHMDS / toluene; tetrahydrofuran / 0.25 h / -75 °C

6.2: 84 percent / toluene; tetrahydrofuran / 1 h / -75 °C

7.1: 100 percent / DIPEA / CH₂Cl₂ / 16 h / 20 °C

8.1: LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

9.1: 1.56 g / (n-Bu)4NF / tetrahydrofuran / 1 h / 0 °C

10.1: 61 percent / 10-camphorsulfonic acid / CH₂Cl₂ / 4 h / 3 °C

11.1: 73 percent / pyridinium chlorochromate; molecular sieves 4 Angstroem / CH₂Cl₂ / 7 h / 20 °C

12.1: 82 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C

With 2,6-dimethylpyridine; hydrogenchloride; sodium periodate; lithium aluminium tetrahydride; formic acid; 4 A molecular sieve; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;

DOI:10.1271/bbb.67.838

Reference yield:

(3R)-3-[(R)-(3,4-methylenedioxyphenyl)(triisopropylsilyloxy)methyl]-4-butanolide (572916-27-9) → (1R,2S,5S,6S)-4-hydroxy-2,6-bis(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo[3.3.0]octane (58262-61-6,61254-18-0,63427-86-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: KHMDS / toluene; tetrahydrofuran / 0.25 h / -75 °C

1.2: 86 percent / toluene; tetrahydrofuran / 1 h / -75 °C

2.1: 82 percent / DIPEA / CH₂Cl₂ / 16 h / 20 °C

3.1: DIBAL-H / toluene / 1 h / -75 °C

4.1: NaBH₄ / ethanol / 2 h / 20 °C

5.1: 1.56 g / (n-Bu)4NF / tetrahydrofuran / 1 h / 0 °C

6.1: 57 percent / 10-camphorsulfonic acid / CH₂Cl₂ / 40 h / 3 °C

7.1: 73 percent / pyridinium chlorochromate; molecular sieves 4 Angstroem / CH₂Cl₂ / 7 h / 20 °C

8.1: 82 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C

With hydrogenchloride; sodium tetrahydroborate; 4 A molecular sieve; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; In tetrahydrofuran; ethanol; dichloromethane; toluene;

DOI:10.1271/bbb.67.838

upstream raw materials:

(2S,3R,4R)-4-[(S)-(methoxymethoxy)(3,4-methylenedioxyphenyl)methyl]-2-(3,4-methylenedioxyphenyl)-3-tetrahydrofurancarbaldehyde

piperonal

(3R)-3-[(R)-(3,4-methylenedioxyphenyl)(triisopropylsilyloxy)methyl]-4-butanolide

(3R)-3-[(S)-(3,4-methylenedioxyphenyl)(triisopropylsilyloxy)methyl]-4-butanolide

Downstream raw materials:

2-exo,6-exo-bis(3',4'-methylenedioxyphenyl)-3,7-dioxabicyclo[3.3.0]octane

(+)-aptosimon

(+/-)-aptosimon

Refernces