(2R,3S,4S,5R,6R,8R,9S,10S,11R,12R,13R)-3,5:9,11-bis(isopropylidenedioxy)-6,12-bis(methoxymethoxy)-2,4,6,8,10,12-hexamethyl-13-(4-methoxybenzyloxy)pentadecanoic acid

Base Information

Chemical Name:(2R,3S,4S,5R,6R,8R,9S,10S,11R,12R,13R)-3,5:9,11-bis(isopropylidenedioxy)-6,12-bis(methoxymethoxy)-2,4,6,8,10,12-hexamethyl-13-(4-methoxybenzyloxy)pentadecanoic acid
CAS No.:124895-74-5
Molecular Formula:C₃₉H₆₆O₁₂
Molecular Weight:726.946
Hs Code.:

(2R,3S,4S,5R,6R,8R,9S,10S,11R,12R,13R)-3,5:9,11-bis(isopropylidenedioxy)-6,12-bis(methoxymethoxy)-2,4,6,8,10,12-hexamethyl-13-(4-methoxybenzyloxy)pentadecanoic acid

Synonyms:(2R,3S,4S,5R,6R,8R,9S,10S,11R,12R,13R)-3,5:9,11-bis(isopropylidenedioxy)-6,12-bis(methoxymethoxy)-2,4,6,8,10,12-hexamethyl-13-(4-methoxybenzyloxy)pentadecanoic acid

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Chemical Property of (2R,3S,4S,5R,6R,8R,9S,10S,11R,12R,13R)-3,5:9,11-bis(isopropylidenedioxy)-6,12-bis(methoxymethoxy)-2,4,6,8,10,12-hexamethyl-13-(4-methoxybenzyloxy)pentadecanoic acid

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Technology Process of (2R,3S,4S,5R,6R,8R,9S,10S,11R,12R,13R)-3,5:9,11-bis(isopropylidenedioxy)-6,12-bis(methoxymethoxy)-2,4,6,8,10,12-hexamethyl-13-(4-methoxybenzyloxy)pentadecanoic acid

There total 35 articles about (2R,3S,4S,5R,6R,8R,9S,10S,11R,12R,13R)-3,5:9,11-bis(isopropylidenedioxy)-6,12-bis(methoxymethoxy)-2,4,6,8,10,12-hexamethyl-13-(4-methoxybenzyloxy)pentadecanoic acid 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: 78.0%

: 114811-30-2
(2R,3S,4S,5R,6R,8R,9S,10S,11R,12R,13R)-3,5:9,11-bis(isopropylidenedioxy)-6,12-bis(methoxymethoxy)-2,4,6,8,10,12-hexamethyl-13-(4-methoxybenzyloxy)pentadecan-1-ol

: 124895-74-5
(2R,3S,4S,5R,6R,8R,9S,10S,11R,12R,13R)-3,5:9,11-bis(isopropylidenedioxy)-6,12-bis(methoxymethoxy)-2,4,6,8,10,12-hexamethyl-13-(4-methoxybenzyloxy)pentadecanoic acid

Guidance literature:: With jones reagent; In acetone; at -17 ℃;
DOI:10.1016/S0040-4039(00)96566-3

Reference yield:

: 97058-14-5
(2R,3S,4R)-3,5-(Isopropylidenedioxy)-2,4-dimethylpentanal

: 124895-74-5
(2R,3S,4S,5R,6R,8R,9S,10S,11R,12R,13R)-3,5:9,11-bis(isopropylidenedioxy)-6,12-bis(methoxymethoxy)-2,4,6,8,10,12-hexamethyl-13-(4-methoxybenzyloxy)pentadecanoic acid

Guidance literature:: Multi-step reaction with 12 steps

1: 86 percent / 1.5M n-BuLi / hexane; tetrahydrofuran / -50 deg C, -23/-20 deg C, 2.5 h, -80 deg C, 40 min

2: 92 percent / 4N HCl / tetrahydrofuran / 11 h / Ambient temperature

3: 93 percent / imidazole / CH₂Cl₂ / 2 h / Ambient temperature

4: 79 percent / PPTS / CH₂Cl₂ / 2.5 h / Ambient temperature

5: 88 percent / MeI, NaHCO₃ / acetonitrile / 1.5 h / 70 °C

6: 86 percent / 1.5M n-BuLi, diisopropylamine / hexane; tetrahydrofuran / -15 deg C, 30 min, -80 deg C, 1 h

7: 71 percent / H₂ / Raney Ni(W-2) / ethanol / 0.5 h / Ambient temperature

8: 92 percent / oxalyl chloride, DMSO / CH₂Cl₂ / -60 °C

9: 82.9 percent / diethyl ether; tetrahydrofuran / 1 h / -85 °C

10: diisopropylethylamine / CH₂Cl₂ / RT, 50/55 deg C, 11 h

11: 94 percent / 1.0M n-Bu₄NF / tetrahydrofuran / RT, 55/60 deg C, 2 h

12: 78 percent / 2.67M Jones reagent / acetone / 2 h / -17 °C

With 1H-imidazole; hydrogenchloride; n-butyllithium; jones reagent; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; dimethyl sulfoxide; diisopropylamine; N-ethyl-N,N-diisopropylamine; methyl iodide; Raney Ni(W-2); In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; acetone; acetonitrile;
DOI:10.1248/cpb.37.1167

Reference yield:

: 124871-55-2
(2R,3S,4S,5R,6R,7R)-3,5-isopropylidenedioxy-7-(4-methoxybenzyloxy)-6-methoxymethoxy-2,4,6-trimethylnonanol

: 124895-74-5
(2R,3S,4S,5R,6R,8R,9S,10S,11R,12R,13R)-3,5:9,11-bis(isopropylidenedioxy)-6,12-bis(methoxymethoxy)-2,4,6,8,10,12-hexamethyl-13-(4-methoxybenzyloxy)pentadecanoic acid

Guidance literature:: Multi-step reaction with 10 steps

1: Et₃N, DMAP / CH₂Cl₂ / 23 h / Heating

2: 90 percent / 60percent NaH / ethanol; 1,2-dimethoxy-ethane / 2 h / Heating

3: NaIO₄ / H₂O; methanol / 8.5 h / Ambient temperature

4: 86 percent / 1.5M n-BuLi, diisopropylamine / hexane; tetrahydrofuran / -15 deg C, 30 min, -80 deg C, 1 h

5: 71 percent / H₂ / Raney Ni(W-2) / ethanol / 0.5 h / Ambient temperature

6: 92 percent / oxalyl chloride, DMSO / CH₂Cl₂ / -60 °C

7: 82.9 percent / diethyl ether; tetrahydrofuran / 1 h / -85 °C

8: diisopropylethylamine / CH₂Cl₂ / RT, 50/55 deg C, 11 h

9: 94 percent / 1.0M n-Bu₄NF / tetrahydrofuran / RT, 55/60 deg C, 2 h

10: 78 percent / 2.67M Jones reagent / acetone / 2 h / -17 °C

With dmap; sodium periodate; n-butyllithium; jones reagent; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; dimethyl sulfoxide; triethylamine; diisopropylamine; N-ethyl-N,N-diisopropylamine; Raney Ni(W-2); In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; hexane; dichloromethane; water; acetone;
DOI:10.1248/cpb.37.1167