Acetic acid (2E,13E)-(4R,5S,6R,7S,9R,10S,11R,12R)-15-acetoxy-7,9-bis-(tert-butyl-dimethyl-silanyloxy)-4,12-dihydroxy-6,10-bis-(4-methoxy-benzyloxy)-5,11-dimethyl-pentadeca-2,13-dienyl ester

Base Information

• Chemical Name: Acetic acid (2E,13E)-(4R,5S,6R,7S,9R,10S,11R,12R)-15-acetoxy-7,9-bis-(tert-butyl-dimethyl-silanyloxy)-4,12-dihydroxy-6,10-bis-(4-methoxy-benzyloxy)-5,11-dimethyl-pentadeca-2,13-dienyl ester
• CAS No.: 846577-27-3
• Molecular Formula: C₄₉H₈₀O₁₂Si₂
• Molecular Weight: 917.338

Synonyms:Acetic acid (2E,13E)-(4R,5S,6R,7S,9R,10S,11R,12R)-15-acetoxy-7,9-bis-(tert-butyl-dimethyl-silanyloxy)-4,12-dihydroxy-6,10-bis-(4-methoxy-benzyloxy)-5,11-dimethyl-pentadeca-2,13-dienyl ester

Chemical Property of Acetic acid (2E,13E)-(4R,5S,6R,7S,9R,10S,11R,12R)-15-acetoxy-7,9-bis-(tert-butyl-dimethyl-silanyloxy)-4,12-dihydroxy-6,10-bis-(4-methoxy-benzyloxy)-5,11-dimethyl-pentadeca-2,13-dienyl ester

Chemical Property:

Purity/Quality:

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Technology Process of Acetic acid (2E,13E)-(4R,5S,6R,7S,9R,10S,11R,12R)-15-acetoxy-7,9-bis-(tert-butyl-dimethyl-silanyloxy)-4,12-dihydroxy-6,10-bis-(4-methoxy-benzyloxy)-5,11-dimethyl-pentadeca-2,13-dienyl ester

There total 14 articles about Acetic acid (2E,13E)-(4R,5S,6R,7S,9R,10S,11R,12R)-15-acetoxy-7,9-bis-(tert-butyl-dimethyl-silanyloxy)-4,12-dihydroxy-6,10-bis-(4-methoxy-benzyloxy)-5,11-dimethyl-pentadeca-2,13-dienyl 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%

(3R,4S,5R,6S,8R,9S,10R,11R)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5,9-bis-(4-methoxy-benzyloxy)-4,10-dimethyl-trideca-1,12-diene-3,11-diol (846577-26-2) + cis-1,4-bis(acetyloxy)but-2-ene (25260-60-0) → Acetic acid (2E,13E)-(4R,5S,6R,7S,9R,10S,11R,12R)-15-acetoxy-7,9-bis-(tert-butyl-dimethyl-silanyloxy)-4,12-dihydroxy-6,10-bis-(4-methoxy-benzyloxy)-5,11-dimethyl-pentadeca-2,13-dienyl ester (846577-27-3)

Guidance literature:

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 20 ℃;

DOI:10.1021/ol0473400

Reference yield:

(2S,4R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-pentanedial → Acetic acid (2E,13E)-(4R,5S,6R,7S,9R,10S,11R,12R)-15-acetoxy-7,9-bis-(tert-butyl-dimethyl-silanyloxy)-4,12-dihydroxy-6,10-bis-(4-methoxy-benzyloxy)-5,11-dimethyl-pentadeca-2,13-dienyl ester (846577-27-3)

Guidance literature:

Multi-step reaction with 13 steps

1.1: KHMDS; 18-C-6 / tetrahydrofuran / 0.25 h / -78 °C

1.2: 6.3 g / tetrahydrofuran / -78 - 20 °C

2.1: 100 percent / DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

3.1: BH₃*THF / tetrahydrofuran / 0.75 h

3.2: 70 percent / NaBO₃*H₂O / tetrahydrofuran; H₂O / 1 h / 20 °C

4.1: PPTS / CH₂Cl₂ / 20 °C

5.1: 2.03 g / DIBAL / toluene / -78 - 0 °C

6.1: 97 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 0.5 h / -78 - 20 °C

7.1: NaH / tetrahydrofuran / -78 °C

7.2: 96 percent / tetrahydrofuran / -78 - 20 °C

8.1: 97 percent / DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

9.1: 68 percent / Ti(OiPr)4; L-(+)-DET; tert-butyl hydroperoxide / CH₂Cl₂; decane / -20 °C

10.1: 94 percent / Et₃N / CH₂Cl₂ / 1 h / 20 °C

11.1: NaI / butan-2-one / 2 h / Heating

12.1: 1.12 g / Zn / I₂ / methanol / 0.5 h / Heating

13.1: 80 percent / [(benzylidene)(1,3-dimesitylimidazolidin-2-yl)(PCy₃)RuCl₂] / CH₂Cl₂ / 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; borane-THF; oxalyl dichloride; 18-crown-6 ether; diethyl (2R,3R)-tartrate; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; sodium iodide; zinc; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; iodine; In tetrahydrofuran; methanol; decane; hexane; dichloromethane; toluene; butanone; 6.1: Swern oxidation / 7.2: Horner-Wadsworth-Emmons reaction / 9.1: Sharpless asymmetric epoxidation;

DOI:10.1021/ol0473400

Reference yield:

(2Z,7Z)-(4S,6R)-4,6-Bis-(tert-butyl-dimethyl-silanyloxy)-2,8-dimethyl-nona-2,7-diene-1,9-diol (846577-21-7) → Acetic acid (2E,13E)-(4R,5S,6R,7S,9R,10S,11R,12R)-15-acetoxy-7,9-bis-(tert-butyl-dimethyl-silanyloxy)-4,12-dihydroxy-6,10-bis-(4-methoxy-benzyloxy)-5,11-dimethyl-pentadeca-2,13-dienyl ester (846577-27-3)

Guidance literature:

Multi-step reaction with 11 steps

1.1: BH₃*THF / tetrahydrofuran / 0.75 h

1.2: 70 percent / NaBO₃*H₂O / tetrahydrofuran; H₂O / 1 h / 20 °C

2.1: PPTS / CH₂Cl₂ / 20 °C

3.1: 2.03 g / DIBAL / toluene / -78 - 0 °C

4.1: 97 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 0.5 h / -78 - 20 °C

5.1: NaH / tetrahydrofuran / -78 °C

5.2: 96 percent / tetrahydrofuran / -78 - 20 °C

6.1: 97 percent / DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

7.1: 68 percent / Ti(OiPr)4; L-(+)-DET; tert-butyl hydroperoxide / CH₂Cl₂; decane / -20 °C

8.1: 94 percent / Et₃N / CH₂Cl₂ / 1 h / 20 °C

9.1: NaI / butan-2-one / 2 h / Heating

10.1: 1.12 g / Zn / I₂ / methanol / 0.5 h / Heating

11.1: 80 percent / [(benzylidene)(1,3-dimesitylimidazolidin-2-yl)(PCy₃)RuCl₂] / CH₂Cl₂ / 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; borane-THF; oxalyl dichloride; diethyl (2R,3R)-tartrate; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; sodium iodide; zinc; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; iodine; In tetrahydrofuran; methanol; decane; hexane; dichloromethane; toluene; butanone; 4.1: Swern oxidation / 5.2: Horner-Wadsworth-Emmons reaction / 7.1: Sharpless asymmetric epoxidation;

DOI:10.1021/ol0473400

upstream raw materials:

(3R,4S,5R,6S,8R,9S,10R,11R)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5,9-bis-(4-methoxy-benzyloxy)-4,10-dimethyl-trideca-1,12-diene-3,11-diol

cis-1,4-bis(acetyloxy)but-2-ene

(2Z,7Z)-(4S,6R)-4,6-Bis-(tert-butyl-dimethyl-silanyloxy)-2,8-dimethyl-nona-2,7-diene-1,9-diol

(2Z,7Z)-(4S,6R)-4,6-Bis-(tert-butyl-dimethyl-silanyloxy)-2,8-dimethyl-nona-2,7-dienedioic acid dimethyl ester

Downstream raw materials:

C₃₃H₄₄O₈

Benzoic acid (2S,3S,4R,5R,6S)-6-[(2R,3S,4R,5S,6S)-5-hydroxy-3-(4-methoxy-benzyloxy)-4-methyl-6-vinyl-tetrahydro-pyran-2-ylmethyl]-5-(4-methoxy-benzyloxy)-4-methyl-2-vinyl-tetrahydro-pyran-3-yl ester

Benzoic acid (2S,3S,4R,5R,6S)-5-(4-methoxy-benzyloxy)-6-[(2R,3S,4S,5S,6S)-3-(4-methoxy-benzyloxy)-4-methyl-5-methylsulfanylthiocarboxyoxy-6-vinyl-tetrahydro-pyran-2-ylmethyl]-4-methyl-2-vinyl-tetrahydro-pyran-3-yl ester

benzoic acid 6-[6-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3-(4-methoxy-benzyloxy)-4-methyl-5-methylsulfanylthiocarboxyoxy-tetrahydro-pyran-2-ylmethyl]-5-(4-methoxy-benzyloxy)-4-methyl-2-vinyl-tetrahydro-pyran-3-yl ester

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