1-[(Z)-(1S,2S)-1-((1R,2R,3S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-{(1R,2R)-2-[(1S,2R,3S)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxymethoxy-1,3-dimethyl-butyl]-cyclopropyl}-1,3-dimethyl-butyl)-2-methyl-hexa-3,5-dienyloxymethyl]-4-methoxy-benzene

Base Information

• Chemical Name: 1-[(Z)-(1S,2S)-1-((1R,2R,3S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-{(1R,2R)-2-[(1S,2R,3S)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxymethoxy-1,3-dimethyl-butyl]-cyclopropyl}-1,3-dimethyl-butyl)-2-methyl-hexa-3,5-dienyloxymethyl]-4-methoxy-benzene
• CAS No.: 869338-64-7
• Molecular Formula: C₄₄H₈₀O₆Si₂
• Molecular Weight: 761.287

Synonyms:1-[(Z)-(1S,2S)-1-((1R,2R,3S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-{(1R,2R)-2-[(1S,2R,3S)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxymethoxy-1,3-dimethyl-butyl]-cyclopropyl}-1,3-dimethyl-butyl)-2-methyl-hexa-3,5-dienyloxymethyl]-4-methoxy-benzene

Chemical Property of 1-[(Z)-(1S,2S)-1-((1R,2R,3S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-{(1R,2R)-2-[(1S,2R,3S)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxymethoxy-1,3-dimethyl-butyl]-cyclopropyl}-1,3-dimethyl-butyl)-2-methyl-hexa-3,5-dienyloxymethyl]-4-methoxy-benzene

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 1-[(Z)-(1S,2S)-1-((1R,2R,3S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-{(1R,2R)-2-[(1S,2R,3S)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxymethoxy-1,3-dimethyl-butyl]-cyclopropyl}-1,3-dimethyl-butyl)-2-methyl-hexa-3,5-dienyloxymethyl]-4-methoxy-benzene

There total 20 articles about 1-[(Z)-(1S,2S)-1-((1R,2R,3S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-{(1R,2R)-2-[(1S,2R,3S)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxymethoxy-1,3-dimethyl-butyl]-cyclopropyl}-1,3-dimethyl-butyl)-2-methyl-hexa-3,5-dienyloxymethyl]-4-methoxy-benzene 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:

(E)-(R)-5-(4-Methoxy-benzyloxy)-4-methyl-pent-2-enoic acid methyl ester (869338-51-2) → 1-[(Z)-(1S,2S)-1-((1R,2R,3S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-{(1R,2R)-2-[(1S,2R,3S)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxymethoxy-1,3-dimethyl-butyl]-cyclopropyl}-1,3-dimethyl-butyl)-2-methyl-hexa-3,5-dienyloxymethyl]-4-methoxy-benzene (869338-64-7)

Guidance literature:

Multi-step reaction with 19 steps

1.1: 95 percent / DIBAL / CH₂Cl₂; toluene / 2 h / -78 °C

2.1: 90 percent / 3 Angstroem molecular sieves; diethyl (+)-tartrate; t-BuOOH / Ti(O-iPr)4 / CH₂Cl₂; decane / 20 h / -30 °C

3.1: 67 percent / CuI

4.1: 95 percent / OsO₄; NaIO₄

5.1: 99 percent / DDQ / CH₂Cl₂ / 2 h / 0 °C

6.1: imidazole / dimethylformamide / 20 h / 20 °C

7.1: 0.91 g / aq. HCl / ethanol / 0.5 h / 20 °C

8.1: 70 percent / Et₂Zn / 1,2-dichloro-ethane / 3 h / 20 °C

9.1: 95 percent / PPh₃; imidazole; I₂ / benzene; diethyl ether / 1 h / 20 °C

10.1: 95 percent / NaCNBH₃; DMPU / 40 h / 70 °C

11.1: 90 percent / AcOH; TBAF / tetrahydrofuran / 18 h / 20 °C

12.1: imidazole / CH₂Cl₂ / 2 h / 20 °C

13.1: 855 mg / i-Pr₂NEt / CH₂Cl₂ / 24 h / 20 °C

14.1: t-BuLi / tetrahydrofuran; pentane / 0.5 h / -78 °C / y

14.2: 2-ThCuCNLi / tetrahydrofuran; pentane / 0.5 h / -78 - -20 °C

14.3: 63 percent / tetrahydrofuran; pentane / 23 h / -40 - 0 °C

15.1: DIBAL

16.1: 96 percent / Dess-Martin periodinane

17.1: CrCl₂

17.2: KOH / methanol

With 1H-imidazole; chromium dichloride; hydrogenchloride; tert.-butylhydroperoxide; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium periodate; copper(l) iodide; osmium(VIII) oxide; diethyl (2R,3R)-tartrate; 3 A molecular sieve; tetrabutyl ammonium fluoride; iodine; tert.-butyl lithium; diethylzinc; diisobutylaluminium hydride; sodium cyanoborohydride; Dess-Martin periodane; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; titanium(IV) isopropylate; In tetrahydrofuran; diethyl ether; decane; ethanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; pentane; benzene; 6.1: Wittig reaction;

DOI:10.1021/ol051691c

Reference yield:

(2E,4R)-5-(4-methoxybenzyloxy)-4-methyl-2-penten-1-ol (200341-72-6) → 1-[(Z)-(1S,2S)-1-((1R,2R,3S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-{(1R,2R)-2-[(1S,2R,3S)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxymethoxy-1,3-dimethyl-butyl]-cyclopropyl}-1,3-dimethyl-butyl)-2-methyl-hexa-3,5-dienyloxymethyl]-4-methoxy-benzene (869338-64-7)

Guidance literature:

Multi-step reaction with 18 steps

1.1: 90 percent / 3 Angstroem molecular sieves; diethyl (+)-tartrate; t-BuOOH / Ti(O-iPr)4 / CH₂Cl₂; decane / 20 h / -30 °C

2.1: 67 percent / CuI

3.1: 95 percent / OsO₄; NaIO₄

4.1: 99 percent / DDQ / CH₂Cl₂ / 2 h / 0 °C

5.1: imidazole / dimethylformamide / 20 h / 20 °C

6.1: 0.91 g / aq. HCl / ethanol / 0.5 h / 20 °C

7.1: 70 percent / Et₂Zn / 1,2-dichloro-ethane / 3 h / 20 °C

8.1: 95 percent / PPh₃; imidazole; I₂ / benzene; diethyl ether / 1 h / 20 °C

9.1: 95 percent / NaCNBH₃; DMPU / 40 h / 70 °C

10.1: 90 percent / AcOH; TBAF / tetrahydrofuran / 18 h / 20 °C

11.1: imidazole / CH₂Cl₂ / 2 h / 20 °C

12.1: 855 mg / i-Pr₂NEt / CH₂Cl₂ / 24 h / 20 °C

13.1: t-BuLi / tetrahydrofuran; pentane / 0.5 h / -78 °C / y

13.2: 2-ThCuCNLi / tetrahydrofuran; pentane / 0.5 h / -78 - -20 °C

13.3: 63 percent / tetrahydrofuran; pentane / 23 h / -40 - 0 °C

14.1: DIBAL

15.1: 96 percent / Dess-Martin periodinane

16.1: CrCl₂

16.2: KOH / methanol

With 1H-imidazole; chromium dichloride; hydrogenchloride; tert.-butylhydroperoxide; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium periodate; copper(l) iodide; osmium(VIII) oxide; diethyl (2R,3R)-tartrate; 3 A molecular sieve; tetrabutyl ammonium fluoride; iodine; tert.-butyl lithium; diethylzinc; diisobutylaluminium hydride; sodium cyanoborohydride; Dess-Martin periodane; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; titanium(IV) isopropylate; In tetrahydrofuran; diethyl ether; decane; ethanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; pentane; benzene; 5.1: Wittig reaction;

DOI:10.1021/ol051691c

Reference yield:

(2S,3R,4S)-4-((1S,2S)-2-Iodo-cyclopropyl)-2-methyl-pentane-1,3-diol (869338-56-7) → 1-[(Z)-(1S,2S)-1-((1R,2R,3S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-{(1R,2R)-2-[(1S,2R,3S)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxymethoxy-1,3-dimethyl-butyl]-cyclopropyl}-1,3-dimethyl-butyl)-2-methyl-hexa-3,5-dienyloxymethyl]-4-methoxy-benzene (869338-64-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: imidazole / CH₂Cl₂ / 2 h / 20 °C

2.1: 855 mg / i-Pr₂NEt / CH₂Cl₂ / 24 h / 20 °C

3.1: t-BuLi / tetrahydrofuran; pentane / 0.5 h / -78 °C / y

3.2: 2-ThCuCNLi / tetrahydrofuran; pentane / 0.5 h / -78 - -20 °C

3.3: 63 percent / tetrahydrofuran; pentane / 23 h / -40 - 0 °C

4.1: DIBAL

5.1: 96 percent / Dess-Martin periodinane

6.1: CrCl₂

6.2: KOH / methanol

With 1H-imidazole; chromium dichloride; tert.-butyl lithium; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; pentane;

DOI:10.1021/ol051691c

upstream raw materials:

(1-bromoallyl)trimethylsilane

(2S,3R,4S)-4-((1S,2S)-2-Iodo-cyclopropyl)-2-methyl-pentane-1,3-diol

(E)-(R)-5-(4-Methoxy-benzyloxy)-4-methyl-pent-2-enoic acid methyl ester

{(2S,3S)-3-[(S)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-oxiranyl}-methanol

Downstream raw materials:

(2S,3R,4S)-4-{(1R,2R)-2-[(Z)-(2S,3R,4R,5S,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4,6-trimethyl-deca-7,9-dienyl]-cyclopropyl}-3-methoxymethoxy-2-methyl-pentan-1-ol

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