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

Base Information

• Chemical Name: (2R,3S,4S,5R,8R,9S,10S,11R,12R,13R)-3,5:9,11-bis(isopropylidenedioxy)-1-tert-butyldiphenylsilyloxy-13-(4-methoxybenzyloxy)-12-methoxymethoxy-2,4,8,10,12-pentamethylpentadecan-6-one
• CAS No.: 114811-27-7
• Molecular Formula: C₅₂H₇₈O₁₀Si
• Molecular Weight: 891.271
• Mol file: 114811-27-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 32 articles about (2R,3S,4S,5R,8R,9S,10S,11R,12R,13R)-3,5:9,11-bis(isopropylidenedioxy)-1-tert-butyldiphenylsilyloxy-13-(4-methoxybenzyloxy)-12-methoxymethoxy-2,4,8,10,12-pentamethylpentadecan-6-one 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: 92.0%

(2R,3S,4S,5R,6RS,8R,9S,10S,11R,12R,13R)-3,5:9,11-bis(isopropylidenedioxy)-1-tert-butyldiphenylsilyloxy-13-(4-methoxybenzyloxy)-12-methoxymethoxy-2,4,8,10,12-pentamethylpentadecan-6-ol (114811-26-6,124987-22-0,124987-23-1) → (2R,3S,4S,5R,8R,9S,10S,11R,12R,13R)-3,5:9,11-bis(isopropylidenedioxy)-1-tert-butyldiphenylsilyloxy-13-(4-methoxybenzyloxy)-12-methoxymethoxy-2,4,8,10,12-pentamethylpentadecan-6-one (114811-27-7)

Guidance literature:

With COCl₂; In dimethyl sulfoxide; triethylamine;

DOI:10.1016/S0040-4039(00)96566-3

Reference yield:

(2R,3S,4R)-3,5-(Isopropylidenedioxy)-2,4-dimethylpentanal (97058-14-5) → (2R,3S,4S,5R,8R,9S,10S,11R,12R,13R)-3,5:9,11-bis(isopropylidenedioxy)-1-tert-butyldiphenylsilyloxy-13-(4-methoxybenzyloxy)-12-methoxymethoxy-2,4,8,10,12-pentamethylpentadecan-6-one (114811-27-7)

Guidance literature:

Multi-step reaction with 8 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

With 1H-imidazole; hydrogenchloride; n-butyllithium; oxalyl dichloride; hydrogen; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; dimethyl sulfoxide; diisopropylamine; methyl iodide; Raney Ni(W-2); In tetrahydrofuran; 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,8R,9S,10S,11R,12R,13R)-3,5:9,11-bis(isopropylidenedioxy)-1-tert-butyldiphenylsilyloxy-13-(4-methoxybenzyloxy)-12-methoxymethoxy-2,4,8,10,12-pentamethylpentadecan-6-one (114811-27-7)

Guidance literature:

Multi-step reaction with 4 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

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

DOI:10.1248/cpb.37.1167

upstream raw materials:

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

(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

(2R,3S,4S,5R)-6-tert-butyldiphenylsilyloxy-3,5-dimethyl-2,4-isopropylidenedioxyhexanal

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)pentadecan-1-ol

(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)-1-tert-butyldiphenylsilyloxy-2,4,6,8,10,12-hexamethyl-13-(4-methoxybenzyloxy)pentadecane

(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