(2R,3S,7R,8RS,11R,12R)-1-t-butyldiphenylsilyloxy-11,12-(isopropylidenedioxy)-3,7-oxido-2,8-tetracosanediol di-p-toluenesulfonate

Base Information

• Chemical Name: (2R,3S,7R,8RS,11R,12R)-1-t-butyldiphenylsilyloxy-11,12-(isopropylidenedioxy)-3,7-oxido-2,8-tetracosanediol di-p-toluenesulfonate
• CAS No.: 537665-87-5
• Molecular Formula: C₅₇H₈₂O₁₀S₂Si
• Molecular Weight: 1019.49
• Mol file: 537665-87-5.mol

Synonyms:

Chemical Property of (2R,3S,7R,8RS,11R,12R)-1-t-butyldiphenylsilyloxy-11,12-(isopropylidenedioxy)-3,7-oxido-2,8-tetracosanediol di-p-toluenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,7R,8RS,11R,12R)-1-t-butyldiphenylsilyloxy-11,12-(isopropylidenedioxy)-3,7-oxido-2,8-tetracosanediol di-p-toluenesulfonate

There total 1 articles about (2R,3S,7R,8RS,11R,12R)-1-t-butyldiphenylsilyloxy-11,12-(isopropylidenedioxy)-3,7-oxido-2,8-tetracosanediol di-p-toluenesulfonate 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:

p-toluenesulfonyl chloride (98-59-9) + (2R,3S,7R,8RS,11R,12R)-1-t-butyldiphenylsilyloxy-11,12-(isopropylidenedioxy)-3,7-oxido-2,8-tetracosanediol → (2R,3S,7R,8RS,11R,12R)-1-t-butyldiphenylsilyloxy-11,12-(isopropylidenedioxy)-3,7-oxido-2,8-tetracosanediol di-p-toluenesulfonate (537665-87-5)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 22h;

DOI:10.1016/S0040-4020(03)00135-2

Reference yield:

(2R,3S,7R,8RS,11R,12R)-1-t-butyldiphenylsilyloxy-11,12-(isopropylidenedioxy)-3,7-oxido-2,8-tetracosanediol di-p-toluenesulfonate (537665-87-5) → C54H78O10S2Si (537665-95-5)

Guidance literature:

With acetic acid; In water; at 20 - 50 ℃;

DOI:10.1016/S0040-4020(03)00135-2

Reference yield:

(2R,3S,7R,8RS,11R,12R)-1-t-butyldiphenylsilyloxy-11,12-(isopropylidenedioxy)-3,7-oxido-2,8-tetracosanediol di-p-toluenesulfonate (537665-87-5) → (S)-3-((E)-(2R,10S)-2-(tert-Butyl-diphenyl-silanyloxy)-10-hydroxy-10-{(2S,6R)-6-[(2R,5R)-5-((R)-1-methoxymethoxy-tridecyl)-tetrahydro-furan-2-yl]-tetrahydro-pyran-2-yl}-dec-5-en-7-ynyl)-5-methyl-5H-furan-2-one (485322-68-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 387 mg / AcOH / H₂O / 20 - 50 °C

2.1: 2.4 mg / TBAF / tetrahydrofuran / 20 - 50 °C

3.1: 40 percent / n-BuLi / tetrahydrofuran; hexane / 18 h / -23 - 20 °C

4.1: tetrahydrofuran; hexane / 1 h / -78 °C

4.2: 232 mg / BF₃*Et₂O / tetrahydrofuran / 2 h / -78 °C

5.1: 199 mg / K₂CO₃ / methanol / 5 h / 20 °C

6.1: 79 percent / Et₃N; CuI / (Ph₃P)2PdCl₂ / 2 h / 20 °C

With copper(l) iodide; n-butyllithium; tetrabutyl ammonium fluoride; potassium carbonate; acetic acid; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; methanol; hexane; water;

DOI:10.1016/S0040-4020(03)00135-2

upstream raw materials:

p-toluenesulfonyl chloride

Downstream raw materials:

C₅₄H₇₈O₁₀S₂Si

(S)-3-((E)-(2R,10S)-2-(tert-Butyl-diphenyl-silanyloxy)-10-hydroxy-10-{(2S,6R)-6-[(2R,5R)-5-((R)-1-methoxymethoxy-tridecyl)-tetrahydro-furan-2-yl]-tetrahydro-pyran-2-yl}-dec-5-en-7-ynyl)-5-methyl-5H-furan-2-one

muconin 4-O-(t-butyldiphenylsilyl)-22-O-(methoxymethyl) diether