(1R,3S,4S,5R)-3-Benzenesulfonylmethyl-3-hydroxy-1,4,5-tris-trimethylsilanyloxy-cyclohexanecarboxylic acid methyl ester

Base Information

• Chemical Name: (1R,3S,4S,5R)-3-Benzenesulfonylmethyl-3-hydroxy-1,4,5-tris-trimethylsilanyloxy-cyclohexanecarboxylic acid methyl ester
• CAS No.: 203920-79-0
• Molecular Formula: C₂₄H₄₄O₈SSi₃
• Molecular Weight: 576.931
• Mol file: 203920-79-0.mol

Synonyms:

Chemical Property of (1R,3S,4S,5R)-3-Benzenesulfonylmethyl-3-hydroxy-1,4,5-tris-trimethylsilanyloxy-cyclohexanecarboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3S,4S,5R)-3-Benzenesulfonylmethyl-3-hydroxy-1,4,5-tris-trimethylsilanyloxy-cyclohexanecarboxylic acid methyl ester

There total 5 articles about (1R,3S,4S,5R)-3-Benzenesulfonylmethyl-3-hydroxy-1,4,5-tris-trimethylsilanyloxy-cyclohexanecarboxylic acid methyl ester 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: 65.0%

methylphenylsulfonate (3112-85-4) + 1,4,5-tris-O-trimethylsilyl-3-deshydroquinate de methyle (134252-20-3) → (1R,3S,4S,5R)-3-Benzenesulfonylmethyl-3-hydroxy-1,4,5-tris-trimethylsilanyloxy-cyclohexanecarboxylic acid methyl ester (203920-79-0)

Guidance literature:

With ethylmagnesium bromide; In diethyl ether; benzene; for 12h; Ambient temperature;

Reference yield: 22.0%

methylphenylsulfonate (3112-85-4) + 1,4,5-tris-O-trimethylsilyl-3-deshydroquinate de methyle (134252-20-3) → (1R,3R,4S,5R)-3-Benzenesulfonylmethyl-3-hydroxy-1,4,5-tris-trimethylsilanyloxy-cyclohexanecarboxylic acid methyl ester + (1R,3S,4S,5R)-3-Benzenesulfonylmethyl-3-hydroxy-1,4,5-tris-trimethylsilanyloxy-cyclohexanecarboxylic acid methyl ester (203920-79-0)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -35 ℃; for 3h;

Reference yield:

3-dehydroquinic acid (10534-44-8) → (1R,3S,4S,5R)-3-Benzenesulfonylmethyl-3-hydroxy-1,4,5-tris-trimethylsilanyloxy-cyclohexanecarboxylic acid methyl ester (203920-79-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 50 percent / Amberlite resin

2: 75 percent / hexamethyldisilazane / pyridine

3: 22 percent / LDA / tetrahydrofuran / 3 h / -35 °C

With Amberlite resin; 1,1,1,3,3,3-hexamethyl-disilazane; lithium diisopropyl amide; In tetrahydrofuran; pyridine;

upstream raw materials:

methylphenylsulfonate

1,4,5-tris-O-trimethylsilyl-3-deshydroquinate de methyle

3-dehydroquinic acid

D-(-)-quinic acid