Benzaldehyde, 3-chloro-4,6-dihydroxy-2-methyl-5-[(2E,4E)-3-methyl-5-[(6R,7R,8R)-6,7 ,8-trimethyl-1,4-dioxaspiro[4.5]dec-7-yl]-2,4-pentadienyl]-

Base Information

• Chemical Name: Benzaldehyde, 3-chloro-4,6-dihydroxy-2-methyl-5-[(2E,4E)-3-methyl-5-[(6R,7R,8R)-6,7 ,8-trimethyl-1,4-dioxaspiro[4.5]dec-7-yl]-2,4-pentadienyl]-
• CAS No.: 99529-53-0
• Molecular Formula: C25H33ClO5
• Molecular Weight: 448.987
• Mol file: 99529-53-0.mol

Synonyms:

Chemical Property of Benzaldehyde, 3-chloro-4,6-dihydroxy-2-methyl-5-[(2E,4E)-3-methyl-5-[(6R,7R,8R)-6,7 ,8-trimethyl-1,4-dioxaspiro[4.5]dec-7-yl]-2,4-pentadienyl]-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzaldehyde, 3-chloro-4,6-dihydroxy-2-methyl-5-[(2E,4E)-3-methyl-5-[(6R,7R,8R)-6,7 ,8-trimethyl-1,4-dioxaspiro[4.5]dec-7-yl]-2,4-pentadienyl]-

There total 63 articles about Benzaldehyde, 3-chloro-4,6-dihydroxy-2-methyl-5-[(2E,4E)-3-methyl-5-[(6R,7R,8R)-6,7 ,8-trimethyl-1,4-dioxaspiro[4.5]dec-7-yl]-2,4-pentadienyl]- 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:

(2E,4E,1'R,2'R,6'R)-(-)-5-(3',3'-ethylenedioxy-1',2',6'-trimethylcyclohexyl)-3-methyl-2,4-pentadien-1-ol (99529-50-7) → 3-Chloro-4,6-dihydroxy-2-methyl-5-[(2E,4E)-3-methyl-5-((6R,7R,8R)-6,7,8-trimethyl-1,4-dioxa-spiro[4.5]dec-7-yl)-penta-2,4-dienyl]-benzaldehyde (99529-53-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

1.2: tetrahydrofuran; hexane / 1.5 h / -78 °C

2.1: 77 percent / Li₂CuCl₄ / tetrahydrofuran; hexane / 2.5 h / 0 °C

3.1: benzene-d6 / 40 h / Irradiation

3.2: 65 percent / toluene / 4 h / Heating

4.1: Et₃N; Et₃SiH / Pd(OAc)2 / CH₂Cl₂ / 15 h / 20 °C

4.2: 70 percent / TBAF / CH₂Cl₂; tetrahydrofuran / 0.25 h / 0 °C

5.1: EtMgBr / diethyl ether / 0.5 h / 20 °C

5.2: 0.075 g / diethyl ether / 0.42 h / 100 °C

With triethylsilane; n-butyllithium; dilithium tetrachlorocuprate; ethylmagnesium bromide; triethylamine; palladium diacetate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; benzene-d6;

DOI:10.1021/ol006561c

Reference yield:

(2'E,4'E,1''R,2''R,6''R)-4-chloro-2-<5'-(3'',3''-ethylenedioxy-1'',2'',6''-trimethylcyclohexyl)-3'-methyl-2',4'-pentadienyl>orcinol (99529-52-9) + orthoformic acid triethyl ester (122-51-0) → 3-Chloro-4,6-dihydroxy-2-methyl-5-[(2E,4E)-3-methyl-5-((6R,7R,8R)-6,7,8-trimethyl-1,4-dioxa-spiro[4.5]dec-7-yl)-penta-2,4-dienyl]-benzaldehyde (99529-53-0)

Guidance literature:

With ethylmagnesium bromide; Yield given. Multistep reaction; 1) ether, room temp., 30 min.; 2) ether evaporated; 100 degC, 10 min.;

DOI:10.1016/S0040-4020(01)96657-8

Reference yield:

2,3,4-trimethyl-3-[5'-t-butyldimethylsilyloxy-3'-methyl-(1E,3E)-pentadienyl]-cyclohexanone → 3-Chloro-4,6-dihydroxy-2-methyl-5-[(2E,4E)-3-methyl-5-((6R,7R,8R)-6,7,8-trimethyl-1,4-dioxa-spiro[4.5]dec-7-yl)-penta-2,4-dienyl]-benzaldehyde (99529-53-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: TBAF / dimethylformamide; tetrahydrofuran / 5 h / 0 °C

2.1: 76 percent / p-TsOH; CaSO₄ / cyclohexane / 3.5 h / 20 °C

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

3.2: tetrahydrofuran; hexane / 1.5 h / -78 °C

4.1: 77 percent / Li₂CuCl₄ / tetrahydrofuran; hexane / 2.5 h / 0 °C

5.1: benzene-d6 / 40 h / Irradiation

5.2: 65 percent / toluene / 4 h / Heating

6.1: Et₃N; Et₃SiH / Pd(OAc)2 / CH₂Cl₂ / 15 h / 20 °C

6.2: 70 percent / TBAF / CH₂Cl₂; tetrahydrofuran / 0.25 h / 0 °C

7.1: EtMgBr / diethyl ether / 0.5 h / 20 °C

7.2: 0.075 g / diethyl ether / 0.42 h / 100 °C

With triethylsilane; calcium sulfate; n-butyllithium; dilithium tetrachlorocuprate; ethylmagnesium bromide; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; triethylamine; palladium diacetate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; cyclohexane; benzene-d6; N,N-dimethyl-formamide;

DOI:10.1021/ol006561c

upstream raw materials:

(2'E,4'E,1''R,2''R,6''R)-4-chloro-2-<5'-(3'',3''-ethylenedioxy-1'',2'',6''-trimethylcyclohexyl)-3'-methyl-2',4'-pentadienyl>orcinol

orthoformic acid triethyl ester

(2E,4E,1'R,2'R,6'R)-(-)-5-(3',3'-ethylenedioxy-1',2',6'-trimethylcyclohexyl)-3-methyl-2,4-pentadien-1-ol

2,3,4-trimethyl-3-[5'-hydroxy-3'-methyl-(1E,3E)-pentadienyl]cyclohexanone

Downstream raw materials:

3-Chloro-4,6-dihydroxy-2-methyl-5-[(2Z,4E)-3-methyl-5-((1S,2S,6S)-1,2,6-trimethyl-3-oxo-cyclohexyl)-penta-2,4-dienyl]-benzaldehyde

(+/-) ascochlorin

Ascochlorin

Refernces

• 1、 Safaryn, J. E.,Chiarello, J.,Chen, K.-M.,Joullie, M. M.. "A CONVENIENT SYNTHESIS OF (+/-) ASCOCHLORIN". . p. 2635 - 2642. Retrieved 2007/10/02.
• 2、 Mori, Kenji,Fujioka, Takafumi. "SYNTHESIS OF (+/-)-ASCOCHLORIN, (+/-)-ASCOFURANONE AND LL-Z1272α". . p. 2711 - 2720. Retrieved 2007/10/02.