(Z)-4-{(2R,6R)-6-[(S)-5-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-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)-5-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-pentyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid 2,4-dimethoxy-benzyl ester
• CAS No.: 334936-16-2
• Molecular Formula: C₄₀H₅₂O₆Si
• Molecular Weight: 656.935

Synonyms:(Z)-4-{(2R,6R)-6-[(S)-5-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-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)-5-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-pentyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid 2,4-dimethoxy-benzyl ester

Chemical Property:

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Technology Process of (Z)-4-{(2R,6R)-6-[(S)-5-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-pentyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid 2,4-dimethoxy-benzyl ester

There total 12 articles about (Z)-4-{(2R,6R)-6-[(S)-5-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-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: 80.0%

{6-[5-(tert-butyl-diphenyl-silanyloxy)-2-methyl-pentyl]-5,6-dihydro-2H-pyran-2-yl}-acetaldehyde (334936-03-7) + [bis-(2,2,2-trifluoro-ethoxy)-phosphoryl]-acetic acid 2,4-dimethoxy-benzyl ester (334936-14-0) → (Z)-4-{(2R,6R)-6-[(S)-5-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-pentyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid 2,4-dimethoxy-benzyl ester (334936-16-2)

Guidance literature:

With 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃;

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

Reference yield:

(S)-Citronellal (5949-05-3) → (Z)-4-{(2R,6R)-6-[(S)-5-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-pentyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid 2,4-dimethoxy-benzyl ester (334936-16-2)

Guidance literature:

Multi-step reaction with 9 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

With 1H-imidazole; titanium(IV) isopropylate; 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; ozone; 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)-5-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-pentyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid 2,4-dimethoxy-benzyl ester (334936-16-2)

Guidance literature:

Multi-step reaction with 8 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

With 1H-imidazole; titanium(IV) isopropylate; dmap; palladium diacetate; Grubbs catalyst first generation; 18-crown-6 ether; (S)-[1,1']-binaphthalenyl-2,2'-diol; lithium perchlorate; potassium hexamethylsilazane; diisobutylaluminium hydride; ozone; 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:

{6-[5-(tert-butyl-diphenyl-silanyloxy)-2-methyl-pentyl]-5,6-dihydro-2H-pyran-2-yl}-acetaldehyde

[bis-(2,2,2-trifluoro-ethoxy)-phosphoryl]-acetic acid 2,4-dimethoxy-benzyl ester

(S)-Citronellal

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

Downstream 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

(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

(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

(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

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