(Z)-4-{(2S,6R)-6-[(2R,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((S)-1-hydroxy-2-triethylsilanyloxy-ethyl)-tetrahydro-pyran-2-ylmethyl]-4-methylene-tetrahydro-pyran-2-yl}-but-2-enoic acid 4-methoxy-benzyl ester

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Chemical Name:(Z)-4-{(2S,6R)-6-[(2R,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((S)-1-hydroxy-2-triethylsilanyloxy-ethyl)-tetrahydro-pyran-2-ylmethyl]-4-methylene-tetrahydro-pyran-2-yl}-but-2-enoic acid 4-methoxy-benzyl ester
CAS No.:757959-53-8
Molecular Formula:C₄₈H₆₈O₈Si₂
Molecular Weight:829.234
Hs Code.:

(Z)-4-{(2S,6R)-6-[(2R,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((S)-1-hydroxy-2-triethylsilanyloxy-ethyl)-tetrahydro-pyran-2-ylmethyl]-4-methylene-tetrahydro-pyran-2-yl}-but-2-enoic acid 4-methoxy-benzyl ester

Synonyms:(Z)-4-{(2S,6R)-6-[(2R,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((S)-1-hydroxy-2-triethylsilanyloxy-ethyl)-tetrahydro-pyran-2-ylmethyl]-4-methylene-tetrahydro-pyran-2-yl}-but-2-enoic acid 4-methoxy-benzyl ester

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Chemical Property of (Z)-4-{(2S,6R)-6-[(2R,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((S)-1-hydroxy-2-triethylsilanyloxy-ethyl)-tetrahydro-pyran-2-ylmethyl]-4-methylene-tetrahydro-pyran-2-yl}-but-2-enoic acid 4-methoxy-benzyl ester

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Technology Process of (Z)-4-{(2S,6R)-6-[(2R,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((S)-1-hydroxy-2-triethylsilanyloxy-ethyl)-tetrahydro-pyran-2-ylmethyl]-4-methylene-tetrahydro-pyran-2-yl}-but-2-enoic acid 4-methoxy-benzyl ester

There total 13 articles about (Z)-4-{(2S,6R)-6-[(2R,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((S)-1-hydroxy-2-triethylsilanyloxy-ethyl)-tetrahydro-pyran-2-ylmethyl]-4-methylene-tetrahydro-pyran-2-yl}-but-2-enoic acid 4-methoxy-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%

: 994-30-9
triethylsilyl chloride

: 757959-52-7
(Z)-4-{(2S,6R)-6-[(2R,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((S)-1,2-dihydroxy-ethyl)-tetrahydro-pyran-2-ylmethyl]-4-methylene-tetrahydro-pyran-2-yl}-but-2-enoic acid 4-methoxy-benzyl ester

: 757959-53-8
(Z)-4-{(2S,6R)-6-[(2R,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((S)-1-hydroxy-2-triethylsilanyloxy-ethyl)-tetrahydro-pyran-2-ylmethyl]-4-methylene-tetrahydro-pyran-2-yl}-but-2-enoic acid 4-methoxy-benzyl ester

Guidance literature:: With 1H-imidazole; In dichloromethane; at -78 ℃; for 0.25h;
DOI:10.1021/ol0488800

Reference yield:

: 620605-70-1
C₁₅H₂₄O₄

: 757959-53-8
(Z)-4-{(2S,6R)-6-[(2R,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((S)-1-hydroxy-2-triethylsilanyloxy-ethyl)-tetrahydro-pyran-2-ylmethyl]-4-methylene-tetrahydro-pyran-2-yl}-but-2-enoic acid 4-methoxy-benzyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: 89 percent / N,N-dimethylaminopyridine / 1 h / 20 °C

2.1: 76 percent / AD-Mix β / 2-methyl-propan-2-ol; H2O / 3 h / 0 °C

3.1: 100 percent / pyridinium p-toluenesulfonic acid / 1,2-dichloro-ethane / 0.33 h / 20 °C

4.1: disiamyl borane / tetrahydrofuran / 3 h / 20 °C

4.2: 83 percent / NaBO₃*4H₂O / H₂O / 1.5 h / 20 °C

5.1: 91 percent / NaIO₄ / RuCl₃ / CCl₄; acetonitrile; H₂O / 3 h / 0 °C

6.1: aq. NaOH / methanol / 1 h / 20 °C

6.2: Dowex CCR-3 acidic resin / methanol / 0.5 h

7.1: 135.2 mg / PPh₃; diisopropylazodicarboxylate / tetrahydrofuran / 1 h / 20 °C

8.1: 99 percent / imidazole / CH₂Cl₂ / 20 °C

9.1: Dibal-H / CH₂Cl₂ / 0.08 h / -78 °C

9.2: 71 percent / 18-crown-6; potassium bis(trimethylsilyl)amide / toluene; tetrahydrofuran; CH₂Cl₂ / -78 - -30 °C

10.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

10.2: 96 percent / H₂O / CH₂Cl₂ / 2 h / 20 °C

11.1: 71 percent / tetrahydrofuran; toluene / 30 h / Heating

12.1: 80 percent / p-TsOH / methanol / 3 h / 40 °C

13.1: 80 percent / imidazole / CH₂Cl₂ / 0.25 h / -78 °C

With 1H-imidazole; dmap; sodium hydroxide; sodium periodate; di-isopropyl azodicarboxylate; pyridinium p-toluenesulfonate; bis-(1,2-dimethylpropyl)borane; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; 1,4-bis(9-O-dihydroquinidine)phthalazine; triphenylphosphine; ruthenium trichloride; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; water; 1,2-dichloro-ethane; toluene; acetonitrile; tert-butyl alcohol; 7.1: Mitsunobu reaction / 9.2: Still-Gennari olefination / 10.1: Dess-Martin oxidation;
DOI:10.1021/ol0488800

Reference yield:

: 757959-42-5
Acetic acid (2S,4R,6R)-2-((2R,4S,6R)-4-acetoxy-6-vinyl-tetrahydro-pyran-2-ylmethyl)-6-vinyl-tetrahydro-pyran-4-yl ester

: 757959-53-8
(Z)-4-{(2S,6R)-6-[(2R,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((S)-1-hydroxy-2-triethylsilanyloxy-ethyl)-tetrahydro-pyran-2-ylmethyl]-4-methylene-tetrahydro-pyran-2-yl}-but-2-enoic acid 4-methoxy-benzyl ester

Guidance literature:: Multi-step reaction with 12 steps

1.1: 76 percent / AD-Mix β / 2-methyl-propan-2-ol; H2O / 3 h / 0 °C

2.1: 100 percent / pyridinium p-toluenesulfonic acid / 1,2-dichloro-ethane / 0.33 h / 20 °C

3.1: disiamyl borane / tetrahydrofuran / 3 h / 20 °C

3.2: 83 percent / NaBO₃*4H₂O / H₂O / 1.5 h / 20 °C

4.1: 91 percent / NaIO₄ / RuCl₃ / CCl₄; acetonitrile; H₂O / 3 h / 0 °C

5.1: aq. NaOH / methanol / 1 h / 20 °C

5.2: Dowex CCR-3 acidic resin / methanol / 0.5 h

6.1: 135.2 mg / PPh₃; diisopropylazodicarboxylate / tetrahydrofuran / 1 h / 20 °C

7.1: 99 percent / imidazole / CH₂Cl₂ / 20 °C

8.1: Dibal-H / CH₂Cl₂ / 0.08 h / -78 °C

8.2: 71 percent / 18-crown-6; potassium bis(trimethylsilyl)amide / toluene; tetrahydrofuran; CH₂Cl₂ / -78 - -30 °C

9.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

9.2: 96 percent / H₂O / CH₂Cl₂ / 2 h / 20 °C

10.1: 71 percent / tetrahydrofuran; toluene / 30 h / Heating

11.1: 80 percent / p-TsOH / methanol / 3 h / 40 °C

12.1: 80 percent / imidazole / CH₂Cl₂ / 0.25 h / -78 °C

With 1H-imidazole; sodium hydroxide; sodium periodate; di-isopropyl azodicarboxylate; pyridinium p-toluenesulfonate; bis-(1,2-dimethylpropyl)borane; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; 1,4-bis(9-O-dihydroquinidine)phthalazine; triphenylphosphine; ruthenium trichloride; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; water; 1,2-dichloro-ethane; toluene; acetonitrile; tert-butyl alcohol; 6.1: Mitsunobu reaction / 8.2: Still-Gennari olefination / 9.1: Dess-Martin oxidation;
DOI:10.1021/ol0488800