Toluene-4-sulfonic acid (1S,2S,3S,4R)-1,2-dihydroxy-3-methoxy-4-triethylsilanyloxy-cyclohexylmethyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (1S,2S,3S,4R)-1,2-dihydroxy-3-methoxy-4-triethylsilanyloxy-cyclohexylmethyl ester
• CAS No.: 1053729-00-2
• Molecular Formula: C₂₁H₃₆O₇SSi
• Molecular Weight: 460.664
• Mol file: 1053729-00-2.mol

Synonyms:

Chemical Property of Toluene-4-sulfonic acid (1S,2S,3S,4R)-1,2-dihydroxy-3-methoxy-4-triethylsilanyloxy-cyclohexylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (1S,2S,3S,4R)-1,2-dihydroxy-3-methoxy-4-triethylsilanyloxy-cyclohexylmethyl ester

There total 10 articles about Toluene-4-sulfonic acid (1S,2S,3S,4R)-1,2-dihydroxy-3-methoxy-4-triethylsilanyloxy-cyclohexylmethyl 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:

(1R,3S,4S,5R)-3-bromo-1-hydroxy-7-oxo-6-oxabicyclo[3.2.1]oct-4-yl benzoate (105539-78-4) → Toluene-4-sulfonic acid (1S,2S,3S,4R)-1,2-dihydroxy-3-methoxy-4-triethylsilanyloxy-cyclohexylmethyl ester (1053729-00-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 97 percent / n-Bu₃SnH, AIBN / benzene / 4 h / Heating

2: 89 percent / K₂CO₃ / 1 h / Ambient temperature

3: 1.) imidazole, 2.) pyridinium chlorochromate, 3 A molecular sieves, pyridine, 3.) POCl₃, pyridine

4: 0.8 g / NaBH₄ / methanol / 0.08 h / 0 °C

5: 88 percent / Ag₂O / CH₂Cl₂ / 48 h / Heating

6: 94 percent / n-Bu₄NF*3H₂O / tetrahydrofuran / 3 h / Ambient temperature

7: 83 percent / pyridine / 0.5 h / Ambient temperature

8: 91 percent / OsO₄, NMO, pyridine / 0.5 h / Heating

9: 60 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

10: Et₃N, DMAP / CH₂Cl₂ / 36 h / Ambient temperature

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; 2,2'-azobis(isobutyronitrile); 3 A molecular sieve; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; potassium carbonate; triethylamine; pyridinium chlorochromate; silver(l) oxide; trichlorophosphate; In tetrahydrofuran; methanol; dichloromethane; benzene;

DOI:10.1016/S0957-4166(98)00284-5

Reference yield:

(3S,4R)-4-hydroxy-1-methoxycarbonyl-3-methyloxy-cyclohex-1-ene (215370-53-9) → Toluene-4-sulfonic acid (1S,2S,3S,4R)-1,2-dihydroxy-3-methoxy-4-triethylsilanyloxy-cyclohexylmethyl ester (1053729-00-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 83 percent / pyridine / 0.5 h / Ambient temperature

2: 91 percent / OsO₄, NMO, pyridine / 0.5 h / Heating

3: 60 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

4: Et₃N, DMAP / CH₂Cl₂ / 36 h / Ambient temperature

With pyridine; dmap; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0957-4166(98)00284-5

Reference yield:

(1S,3R,4R)-1-methoxycarbonyl-cyclohexane-1,3,4-triol (215370-46-0) → Toluene-4-sulfonic acid (1S,2S,3S,4R)-1,2-dihydroxy-3-methoxy-4-triethylsilanyloxy-cyclohexylmethyl ester (1053729-00-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) imidazole, 2.) pyridinium chlorochromate, 3 A molecular sieves, pyridine, 3.) POCl₃, pyridine

2: 0.8 g / NaBH₄ / methanol / 0.08 h / 0 °C

3: 88 percent / Ag₂O / CH₂Cl₂ / 48 h / Heating

4: 94 percent / n-Bu₄NF*3H₂O / tetrahydrofuran / 3 h / Ambient temperature

5: 83 percent / pyridine / 0.5 h / Ambient temperature

6: 91 percent / OsO₄, NMO, pyridine / 0.5 h / Heating

7: 60 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

8: Et₃N, DMAP / CH₂Cl₂ / 36 h / Ambient temperature

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; 3 A molecular sieve; tetrabutyl ammonium fluoride; triethylamine; pyridinium chlorochromate; silver(l) oxide; trichlorophosphate; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/S0957-4166(98)00284-5

upstream raw materials:

p-toluenesulfonyl chloride

(1S,2S,3R,4R)-1-hydroxymethyl-4-triethylsilyloxy-3-methoxy-1-cyclohexane-1,2-diol

(1R,3S,4S,5R)-3-bromo-1-hydroxy-7-oxo-6-oxabicyclo[3.2.1]oct-4-yl benzoate

(3S,4R)-4-hydroxy-1-methoxycarbonyl-3-methyloxy-cyclohex-1-ene