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

Base Information

Chemical Name:(5R,6R,9R,10R,13R,14R)-5,14-di(methoxymethoxy)-24-(p-methoxybenzyloxy)methoxy-6,9,10,13-dioxidotricos-1-yne
CAS No.:720678-26-2
Molecular Formula:C₃₇H₆₀O₉
Molecular Weight:648.878
Hs Code.:

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

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

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

There total 20 articles about (5R,6R,9R,10R,13R,14R)-5,14-di(methoxymethoxy)-24-(p-methoxybenzyloxy)methoxy-6,9,10,13-dioxidotricos-1-yne 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: 98.0%

: 720678-44-4
(5R,6R,9R,10R,13R,14R)-1,1-dibromo-5,14-di(methoxymethoxy)-24-(p-methoxybenzyloxy)methoxy-6,9,10,13-dioxidotricos-1-ene

: 720678-26-2
(5R,6R,9R,10R,13R,14R)-5,14-di(methoxymethoxy)-24-(p-methoxybenzyloxy)methoxy-6,9,10,13-dioxidotricos-1-yne

Guidance literature:: With ethylmagnesium bromide; In tetrahydrofuran; at 0 ℃; for 0.5h;
DOI:10.1002/chem.200305557

Reference yield:

: 202067-11-6
(4R,5R)-4,5-isopropylidenedioxy-14-en-pentadecanol

: 720678-26-2
(5R,6R,9R,10R,13R,14R)-5,14-di(methoxymethoxy)-24-(p-methoxybenzyloxy)methoxy-6,9,10,13-dioxidotricos-1-yne

Guidance literature:: Multi-step reaction with 17 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

14.1: 95 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

15.1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 1 h / -78 °C

16.1: PPh₃ / CH₂Cl₂ / 0.17 h / 0 °C

16.2: 90.0 mg / Et₃N / CH₂Cl₂ / 16 h / 0 °C

17.1: 98 percent / ethylmagnesium bromide / tetrahydrofuran / 0.5 h / 0 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; ethylmagnesium bromide; tetrabutyl ammonium fluoride; iodine; sodium hexamethyldisilazane; sodium hydrogencarbonate; toluene-4-sulfonic acid; rhenium(VII) oxide; dimethyl sulfoxide; 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:

: 202067-20-7
(4R,5R)-1-iodo-4,5-isopropylidenedioxy-14-pentadecene

: 720678-26-2
(5R,6R,9R,10R,13R,14R)-5,14-di(methoxymethoxy)-24-(p-methoxybenzyloxy)methoxy-6,9,10,13-dioxidotricos-1-yne

Guidance literature:: Multi-step reaction with 16 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

13.1: 95 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

14.1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 1 h / -78 °C

15.1: PPh₃ / CH₂Cl₂ / 0.17 h / 0 °C

15.2: 90.0 mg / Et₃N / CH₂Cl₂ / 16 h / 0 °C

16.1: 98 percent / ethylmagnesium bromide / tetrahydrofuran / 0.5 h / 0 °C

With pyridine; 2,6-dimethylpyridine; dmap; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; ethylmagnesium bromide; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; sodium hydrogencarbonate; toluene-4-sulfonic acid; rhenium(VII) oxide; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile; 2.1: Wittig coupling;
DOI:10.1002/chem.200305557