(Z)-4-[(2R,6R)-6-((S)-2-Methyl-5-oxo-pentyl)-5,6-dihydro-2H-pyran-2-yl]-but-2-enoic acid 2,4-dimethoxy-benzyl ester

Base Information

• Chemical Name: (Z)-4-[(2R,6R)-6-((S)-2-Methyl-5-oxo-pentyl)-5,6-dihydro-2H-pyran-2-yl]-but-2-enoic acid 2,4-dimethoxy-benzyl ester
• CAS No.: 334936-18-4
• Molecular Formula: C₂₄H₃₂O₆
• Molecular Weight: 416.514
• Mol file: 334936-18-4.mol

Synonyms:(Z)-4-[(2R,6R)-6-((S)-2-Methyl-5-oxo-pentyl)-5,6-dihydro-2H-pyran-2-yl]-but-2-enoic acid 2,4-dimethoxy-benzyl ester

Chemical Property of (Z)-4-[(2R,6R)-6-((S)-2-Methyl-5-oxo-pentyl)-5,6-dihydro-2H-pyran-2-yl]-but-2-enoic acid 2,4-dimethoxy-benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-4-[(2R,6R)-6-((S)-2-Methyl-5-oxo-pentyl)-5,6-dihydro-2H-pyran-2-yl]-but-2-enoic acid 2,4-dimethoxy-benzyl ester

There total 15 articles about (Z)-4-[(2R,6R)-6-((S)-2-Methyl-5-oxo-pentyl)-5,6-dihydro-2H-pyran-2-yl]-but-2-enoic acid 2,4-dimethoxy-benzyl ester 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: 90.0%

(Z)-4-[(2R,6R)-6-((S)-5-Hydroxy-2-methyl-pentyl)-5,6-dihydro-2H-pyran-2-yl]-but-2-enoic acid 2,4-dimethoxy-benzyl ester (334936-31-1) → (Z)-4-[(2R,6R)-6-((S)-2-Methyl-5-oxo-pentyl)-5,6-dihydro-2H-pyran-2-yl]-but-2-enoic acid 2,4-dimethoxy-benzyl ester (334936-18-4)

Guidance literature:

(Z)-4-[(2R,6R)-6-((S)-5-Hydroxy-2-methyl-pentyl)-5,6-dihydro-2H-pyran-2-yl]-but-2-enoic acid 2,4-dimethoxy-benzyl ester; With phosgene; dimethyl sulfoxide; at -78 ℃;

With triethylamine; at -78 - 20 ℃;

DOI:10.1016/S0040-4039(00)02116-X

Reference yield:

(S)-Citronellal (5949-05-3) → (Z)-4-[(2R,6R)-6-((S)-2-Methyl-5-oxo-pentyl)-5,6-dihydro-2H-pyran-2-yl]-but-2-enoic acid 2,4-dimethoxy-benzyl ester (334936-18-4)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 80 percent / PDC / dimethylformamide / 20 °C

2.1: ozone / methanol / -78 °C

2.2: 82 percent / NaBH₄

3.1: 89 percent / DMAP; imidazole / dimethylformamide / 10 h / 20 °C

4.1: 85 percent / DIBAL / CH₂Cl₂ / 1.5 h / -78 °C

5.1: 80 percent / (S)-BINOL; Ti(Oi-Pr)4

6.1: 83 percent / Pd(OAc)2 / acetonitrile / 20 h / Heating

7.1: 85 percent / Cl₂(PCy₃)2Ru=CHPh / CH₂Cl₂ / 36 h / 20 °C

8.1: 78 percent / EtOAc; LiClO₄

9.1: 80 percent / KHMDS; 18-crown-6 / tetrahydrofuran / -78 °C

10.1: 91 percent / HF-pyridine / tetrahydrofuran

11.1: (COCl₂); DMSO / -78 °C

11.2: 90 percent / Et₃N / -78 - 20 °C

With 1H-imidazole; titanium(IV) isopropylate; phosgene; dmap; palladium diacetate; dipyridinium dichromate; Grubbs catalyst first generation; 18-crown-6 ether; (S)-[1,1']-binaphthalenyl-2,2'-diol; lithium perchlorate; potassium hexamethylsilazane; diisobutylaluminium hydride; pyridine hydrogenfluoride; ozone; dimethyl sulfoxide; ethyl acetate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 8.1: Ferrier rearrangement;

DOI:10.1016/S0040-4039(00)02116-X

Reference yield:

(S)-(-)-citronellic acid,methyl ester (56994-89-9) → (Z)-4-[(2R,6R)-6-((S)-2-Methyl-5-oxo-pentyl)-5,6-dihydro-2H-pyran-2-yl]-but-2-enoic acid 2,4-dimethoxy-benzyl ester (334936-18-4)

Guidance literature:

Multi-step reaction with 10 steps

1.1: ozone / methanol / -78 °C

1.2: 82 percent / NaBH₄

2.1: 89 percent / DMAP; imidazole / dimethylformamide / 10 h / 20 °C

3.1: 85 percent / DIBAL / CH₂Cl₂ / 1.5 h / -78 °C

4.1: 80 percent / (S)-BINOL; Ti(Oi-Pr)4

5.1: 83 percent / Pd(OAc)2 / acetonitrile / 20 h / Heating

6.1: 85 percent / Cl₂(PCy₃)2Ru=CHPh / CH₂Cl₂ / 36 h / 20 °C

7.1: 78 percent / EtOAc; LiClO₄

8.1: 80 percent / KHMDS; 18-crown-6 / tetrahydrofuran / -78 °C

9.1: 91 percent / HF-pyridine / tetrahydrofuran

10.1: (COCl₂); DMSO / -78 °C

10.2: 90 percent / Et₃N / -78 - 20 °C

With 1H-imidazole; titanium(IV) isopropylate; phosgene; dmap; palladium diacetate; Grubbs catalyst first generation; 18-crown-6 ether; (S)-[1,1']-binaphthalenyl-2,2'-diol; lithium perchlorate; potassium hexamethylsilazane; diisobutylaluminium hydride; pyridine hydrogenfluoride; ozone; dimethyl sulfoxide; ethyl acetate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 7.1: Ferrier rearrangement;

DOI:10.1016/S0040-4039(00)02116-X

upstream raw materials:

(Z)-4-[(2R,6R)-6-((S)-5-Hydroxy-2-methyl-pentyl)-5,6-dihydro-2H-pyran-2-yl]-but-2-enoic acid 2,4-dimethoxy-benzyl ester

(S)-Citronellal

(S)-(-)-citronellic acid,methyl ester

methyl (S)-6-hydroxy-3-methylhexanoate

Downstream raw materials:

(Z)-4-[(2R,6R)-6-((S)-4-Hydroxymethyl-2-methyl-pent-4-enyl)-5,6-dihydro-2H-pyran-2-yl]-but-2-enoic acid 2,4-dimethoxy-benzyl ester

(Z)-4-[(2R,6R)-6-((S)-4-Formyl-2-methyl-pent-4-enyl)-5,6-dihydro-2H-pyran-2-yl]-but-2-enoic acid 2,4-dimethoxy-benzyl ester