(2R,3S,4S,5R,6R,8R,9S,10S,11R,12R,13R)-3,5:9,11-bis(isopropylidenedioxy)-6,12-bis(methoxymethoxy)-1-tert-butyldiphenylsilyloxy-2,4,6,8,10,12-hexamethyl-13-(4-methoxybenzyloxy)pentadecane

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)-1-tert-butyldiphenylsilyloxy-2,4,6,8,10,12-hexamethyl-13-(4-methoxybenzyloxy)pentadecane
• CAS No.: 114811-29-9
• Molecular Formula: C₅₅H₈₆O₁₁Si
• Molecular Weight: 951.367
• Mol file: 114811-29-9.mol

Synonyms:(2R,3S,4S,5R,6R,8R,9S,10S,11R,12R,13R)-3,5:9,11-bis(isopropylidenedioxy)-6,12-bis(methoxymethoxy)-1-tert-butyldiphenylsilyloxy-2,4,6,8,10,12-hexamethyl-13-(4-methoxybenzyloxy)pentadecane

Chemical Property of (2R,3S,4S,5R,6R,8R,9S,10S,11R,12R,13R)-3,5:9,11-bis(isopropylidenedioxy)-6,12-bis(methoxymethoxy)-1-tert-butyldiphenylsilyloxy-2,4,6,8,10,12-hexamethyl-13-(4-methoxybenzyloxy)pentadecane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S,5R,6R,8R,9S,10S,11R,12R,13R)-3,5:9,11-bis(isopropylidenedioxy)-6,12-bis(methoxymethoxy)-1-tert-butyldiphenylsilyloxy-2,4,6,8,10,12-hexamethyl-13-(4-methoxybenzyloxy)pentadecane

There total 34 articles about (2R,3S,4S,5R,6R,8R,9S,10S,11R,12R,13R)-3,5:9,11-bis(isopropylidenedioxy)-6,12-bis(methoxymethoxy)-1-tert-butyldiphenylsilyloxy-2,4,6,8,10,12-hexamethyl-13-(4-methoxybenzyloxy)pentadecane 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:

(2R,3S,4R)-3,5-(Isopropylidenedioxy)-2,4-dimethylpentanal (97058-14-5) → (2R,3S,4S,5R,6R,8R,9S,10S,11R,12R,13R)-3,5:9,11-bis(isopropylidenedioxy)-6,12-bis(methoxymethoxy)-1-tert-butyldiphenylsilyloxy-2,4,6,8,10,12-hexamethyl-13-(4-methoxybenzyloxy)pentadecane (114811-29-9)

Guidance literature:

Multi-step reaction with 10 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

With 1H-imidazole; hydrogenchloride; n-butyllithium; oxalyl dichloride; 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; acetonitrile;

DOI:10.1248/cpb.37.1167

Reference yield:

(2R,3S,4S,5R)-6-tert-butyldiphenylsilyloxy-3,5-dimethyl-2,4-isopropylidenedioxyhexanal trimethylene dithioacetal (114825-88-6) → (2R,3S,4S,5R,6R,8R,9S,10S,11R,12R,13R)-3,5:9,11-bis(isopropylidenedioxy)-6,12-bis(methoxymethoxy)-1-tert-butyldiphenylsilyloxy-2,4,6,8,10,12-hexamethyl-13-(4-methoxybenzyloxy)pentadecane (114811-29-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 88 percent / MeI, NaHCO₃ / acetonitrile / 1.5 h / 70 °C

2: 86 percent / 1.5M n-BuLi, diisopropylamine / hexane; tetrahydrofuran / -15 deg C, 30 min, -80 deg C, 1 h

3: 71 percent / H₂ / Raney Ni(W-2) / ethanol / 0.5 h / Ambient temperature

4: 92 percent / oxalyl chloride, DMSO / CH₂Cl₂ / -60 °C

5: 82.9 percent / diethyl ether; tetrahydrofuran / 1 h / -85 °C

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

With n-butyllithium; oxalyl dichloride; hydrogen; sodium hydrogencarbonate; dimethyl sulfoxide; diisopropylamine; N-ethyl-N,N-diisopropylamine; methyl iodide; Raney Ni(W-2); In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; acetonitrile;

DOI:10.1248/cpb.37.1167

Reference yield:

(2R,3S,4S,5R)-6-tert-butyldiphenylsilyloxy-3,5-dimethyl-2,4-isopropylidenedioxyhexanal (114825-89-7) → (2R,3S,4S,5R,6R,8R,9S,10S,11R,12R,13R)-3,5:9,11-bis(isopropylidenedioxy)-6,12-bis(methoxymethoxy)-1-tert-butyldiphenylsilyloxy-2,4,6,8,10,12-hexamethyl-13-(4-methoxybenzyloxy)pentadecane (114811-29-9)

Guidance literature:

Multi-step reaction with 5 steps

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

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

3: 92 percent / oxalyl chloride, DMSO / CH₂Cl₂ / -60 °C

4: 82.9 percent / diethyl ether; tetrahydrofuran / 1 h / -85 °C

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

With n-butyllithium; oxalyl dichloride; hydrogen; dimethyl sulfoxide; diisopropylamine; N-ethyl-N,N-diisopropylamine; Raney Ni(W-2); In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane;

DOI:10.1248/cpb.37.1167

upstream raw materials:

(2R,3S,4S,5R,6R,8R,9S,10S,11R,12R,13R)-3,5:9,11-bis(isopropylidenedioxy)-1-tert-butyldiphenylsilyloxy-2,4,6,8,10,12-hexamethyl-13-(4-methoxybenzyloxy)-12-methoxymethoxypentadecan-6-ol

chloromethyl methyl ether

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

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

Downstream raw materials:

(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

(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