(4R,5R,8R,9R,12R,13R)-1-tert-butyldimethylsilyloxy-4,13-di(methoxymethoxy)-23-(p-methoxybenzyloxy)methoxy-5,8,9,12-dioxidotricosane

Base Information

• Chemical Name: (4R,5R,8R,9R,12R,13R)-1-tert-butyldimethylsilyloxy-4,13-di(methoxymethoxy)-23-(p-methoxybenzyloxy)methoxy-5,8,9,12-dioxidotricosane
• CAS No.: 720678-41-1
• Molecular Formula: C₄₂H₇₆O₁₀Si
• Molecular Weight: 769.145
• Mol file: 720678-41-1.mol

Synonyms:(4R,5R,8R,9R,12R,13R)-1-tert-butyldimethylsilyloxy-4,13-di(methoxymethoxy)-23-(p-methoxybenzyloxy)methoxy-5,8,9,12-dioxidotricosane

Chemical Property of (4R,5R,8R,9R,12R,13R)-1-tert-butyldimethylsilyloxy-4,13-di(methoxymethoxy)-23-(p-methoxybenzyloxy)methoxy-5,8,9,12-dioxidotricosane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5R,8R,9R,12R,13R)-1-tert-butyldimethylsilyloxy-4,13-di(methoxymethoxy)-23-(p-methoxybenzyloxy)methoxy-5,8,9,12-dioxidotricosane

There total 15 articles about (4R,5R,8R,9R,12R,13R)-1-tert-butyldimethylsilyloxy-4,13-di(methoxymethoxy)-23-(p-methoxybenzyloxy)methoxy-5,8,9,12-dioxidotricosane 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:

(4R,5R)-4,5-isopropylidenedioxy-14-en-pentadecanol (202067-11-6) → (4R,5R,8R,9R,12R,13R)-1-tert-butyldimethylsilyloxy-4,13-di(methoxymethoxy)-23-(p-methoxybenzyloxy)methoxy-5,8,9,12-dioxidotricosane (720678-41-1)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 89 percent / I₂; PPh₃; imidazole / CH₂Cl₂ / 20 °C

2.1: 78 percent / NaHCO₃ / acetonitrile / 16 h / Heating

3.1: NaHMDS / tetrahydrofuran / 2 h / -78 °C

3.2: 73 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 16 h / -78 - 20 °C

4.1: 81 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

5.1: Re₂O₇; 2,6-lutidine / CH₂Cl₂ / 20 h

5.2: 76 percent / aq. H₂O₂; NaHCO₃ / 0.33 h / 20 °C

6.1: 91 percent / Et₃N / CH₂Cl₂ / 0.5 h / -30 °C

7.1: 77 percent / aq. TsOH / methanol / 16 h / 20 °C

8.1: 90 percent / pyridine / 3 h / Heating

9.1: 85 percent / LiAlH₄ / diethyl ether / 2 h / Heating

10.1: (i-Pr)2NEt; DMAP / CH₂Cl₂ / 6 h / 20 °C

11.1: 0.511 g / (i-Pr)2NEt / CH₂Cl₂ / 12 h / 0 °C

12.1: 9-BBN / tetrahydrofuran / 4 h / 20 °C

12.2: 87 percent / NaOH; aq. H₂O₂ / tetrahydrofuran / 1 h / 20 °C

13.1: 0.186 g / (i-Pr)2NEt / CH₂Cl₂ / 3 h / 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; tetrabutyl ammonium fluoride; iodine; sodium hexamethyldisilazane; sodium hydrogencarbonate; toluene-4-sulfonic acid; rhenium(VII) oxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile; 3.1: Wittig coupling;

DOI:10.1002/chem.200305557

Reference yield:

(4R,5R)-1-iodo-4,5-isopropylidenedioxy-14-pentadecene (202067-20-7) → (4R,5R,8R,9R,12R,13R)-1-tert-butyldimethylsilyloxy-4,13-di(methoxymethoxy)-23-(p-methoxybenzyloxy)methoxy-5,8,9,12-dioxidotricosane (720678-41-1)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 78 percent / NaHCO₃ / acetonitrile / 16 h / Heating

2.1: NaHMDS / tetrahydrofuran / 2 h / -78 °C

2.2: 73 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 16 h / -78 - 20 °C

3.1: 81 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

4.1: Re₂O₇; 2,6-lutidine / CH₂Cl₂ / 20 h

4.2: 76 percent / aq. H₂O₂; NaHCO₃ / 0.33 h / 20 °C

5.1: 91 percent / Et₃N / CH₂Cl₂ / 0.5 h / -30 °C

6.1: 77 percent / aq. TsOH / methanol / 16 h / 20 °C

7.1: 90 percent / pyridine / 3 h / Heating

8.1: 85 percent / LiAlH₄ / diethyl ether / 2 h / Heating

9.1: (i-Pr)2NEt; DMAP / CH₂Cl₂ / 6 h / 20 °C

10.1: 0.511 g / (i-Pr)2NEt / CH₂Cl₂ / 12 h / 0 °C

11.1: 9-BBN / tetrahydrofuran / 4 h / 20 °C

11.2: 87 percent / NaOH; aq. H₂O₂ / tetrahydrofuran / 1 h / 20 °C

12.1: 0.186 g / (i-Pr)2NEt / CH₂Cl₂ / 3 h / 20 °C

With pyridine; 2,6-dimethylpyridine; dmap; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; sodium hydrogencarbonate; toluene-4-sulfonic acid; rhenium(VII) oxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile; 2.1: Wittig coupling;

DOI:10.1002/chem.200305557

Reference yield:

(4R,5R)-5-hydroxypentadec-14-en-1,4-olide (720678-33-1) → (4R,5R,8R,9R,12R,13R)-1-tert-butyldimethylsilyloxy-4,13-di(methoxymethoxy)-23-(p-methoxybenzyloxy)methoxy-5,8,9,12-dioxidotricosane (720678-41-1)

Guidance literature:

Multi-step reaction with 15 steps

1.1: LiAlH₄ / diethyl ether / 2 h / Heating

2.1: 3.34 g / TsOH / hexane / 6 h / Heating

3.1: 89 percent / I₂; PPh₃; imidazole / CH₂Cl₂ / 20 °C

4.1: 78 percent / NaHCO₃ / acetonitrile / 16 h / Heating

5.1: NaHMDS / tetrahydrofuran / 2 h / -78 °C

5.2: 73 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 16 h / -78 - 20 °C

6.1: 81 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

7.1: Re₂O₇; 2,6-lutidine / CH₂Cl₂ / 20 h

7.2: 76 percent / aq. H₂O₂; NaHCO₃ / 0.33 h / 20 °C

8.1: 91 percent / Et₃N / CH₂Cl₂ / 0.5 h / -30 °C

9.1: 77 percent / aq. TsOH / methanol / 16 h / 20 °C

10.1: 90 percent / pyridine / 3 h / Heating

11.1: 85 percent / LiAlH₄ / diethyl ether / 2 h / Heating

12.1: (i-Pr)2NEt; DMAP / CH₂Cl₂ / 6 h / 20 °C

13.1: 0.511 g / (i-Pr)2NEt / CH₂Cl₂ / 12 h / 0 °C

14.1: 9-BBN / tetrahydrofuran / 4 h / 20 °C

14.2: 87 percent / NaOH; aq. H₂O₂ / tetrahydrofuran / 1 h / 20 °C

15.1: 0.186 g / (i-Pr)2NEt / CH₂Cl₂ / 3 h / 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; tetrabutyl ammonium fluoride; iodine; sodium hexamethyldisilazane; sodium hydrogencarbonate; toluene-4-sulfonic acid; rhenium(VII) oxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetonitrile; 5.1: Wittig coupling;

DOI:10.1002/chem.200305557

upstream raw materials:

(4R,5R)-1-iodo-4,5-isopropylidenedioxy-14-pentadecene

(4R,5R)-4,5-isopropylidenedioxy-14-en-pentadecanol

(4R,5R)-5-hydroxypentadec-14-en-1,4-olide

(4R,5R)-Pentadec-14-ene-1,4,5-triol

Downstream raw materials:

(R)-4-{(2R,5R,2'R,5'R)-5'-[(R)-11-(4-Methoxy-benzyloxymethoxy)-1-methoxymethoxy-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-4-methoxymethoxy-butyraldehyde

(5R,6R,9R,10R,13R,14R)-5,14-di(methoxymethoxy)-24-(p-methoxybenzyloxy)methoxy-6,9,10,13-dioxidotricos-1-yne

(5R,6R,9R,10R,13R,14R)-1,1-dibromo-5,14-di(methoxymethoxy)-24-(p-methoxybenzyloxy)methoxy-6,9,10,13-dioxidotricos-1-ene

{(E,Z)}-4-tert-butyldimethylsilyloxy-15,24-di(methoxymethoxy)-34-(p-methoxybenzyloxy)methyloxyasimicin-9-en-11-yne