(2S^*,6R^*)-7-<(tert-butyldimethylsilyl)oxy>-2,6-dimethyl-1-heptyl p-toluenesulfonate

Base Information

• Chemical Name: (2S^*,6R^*)-7-<(tert-butyldimethylsilyl)oxy>-2,6-dimethyl-1-heptyl p-toluenesulfonate
• CAS No.: 83651-49-4
• Molecular Formula: C₂₂H₄₀O₄SSi
• Molecular Weight: 428.709

Synonyms:(2S^*,6R^*)-7-<(tert-butyldimethylsilyl)oxy>-2,6-dimethyl-1-heptyl p-toluenesulfonate

Chemical Property of (2S^*,6R^*)-7-<(tert-butyldimethylsilyl)oxy>-2,6-dimethyl-1-heptyl p-toluenesulfonate

Chemical Property:

Purity/Quality:

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Technology Process of (2S^*,6R^*)-7-<(tert-butyldimethylsilyl)oxy>-2,6-dimethyl-1-heptyl p-toluenesulfonate

There total 14 articles about (2S^*,6R^*)-7-<(tert-butyldimethylsilyl)oxy>-2,6-dimethyl-1-heptyl 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: 93.0%

(2S,6R)-7-(tert-Butyl-dimethyl-silanyloxy)-2,6-dimethyl-heptan-1-ol (83651-48-3) + p-toluenesulfonyl chloride (98-59-9) → (2S*,6R*)-7-<(tert-butyldimethylsilyl)oxy>-2,6-dimethyl-1-heptyl p-toluenesulfonate (83651-49-4)

Guidance literature:

With pyridine; In dichloromethane; for 22h; Ambient temperature;

DOI:10.1021/jo00244a017

Reference yield:

(S)-2-Methyl-pent-4-ene-1,3-diol (42411-90-5) → Toluene-4-sulfonic acid 7-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-heptyl ester (83651-49-4,92934-90-2,92934-94-6)

Guidance literature:

Multi-step reaction with 6 steps

1: triethylamine, 4-(N,N-dimethylamino)pyridine / CH₂Cl₂

2: CH₂Cl₂

4: hydrogen / PtO₂ / ethyl acetate

5: diborane / tetrahydrofuran / 25 °C

6: C₅H₅N / CH₂Cl₂

With pyridine; dmap; hydrogen; triethylamine; diborane; platinum(IV) oxide; In tetrahydrofuran; dichloromethane; ethyl acetate;

DOI:10.1016/S0040-4039(00)88423-3

Reference yield:

(2R*,3S*)-3-hydroxy-2-methyl-4-pentenoic acid (83651-42-7,86335-92-4,86335-93-5,99529-23-4,113564-12-8) → (2S*,6R*)-7-<(tert-butyldimethylsilyl)oxy>-2,6-dimethyl-1-heptyl p-toluenesulfonate (83651-49-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 90 percent / lithium aluminum hydride / tetrahydrofuran / Heating

2: 100 percent / triethylamine, 4-(N,N-dimethylamino)pyridine / CH₂Cl₂

3: 73 percent / CH₂Cl₂

5: 100 percent / H₂ / PtO₂ / ethyl acetate

6: 83 percent / diborane / tetrahydrofuran / 25 °C

7: 86 percent / C₅H₅N / CH₂Cl₂

With pyridine; dmap; lithium aluminium tetrahydride; hydrogen; triethylamine; diborane; platinum(IV) oxide; In tetrahydrofuran; dichloromethane; ethyl acetate;

DOI:10.1016/S0040-4039(00)88423-3

upstream raw materials:

7-(tert-Butyl-dimethyl-silanyloxy)-2,6-dimethyl-heptan-1-ol

p-toluenesulfonyl chloride

(S)-2-Methyl-pent-4-ene-1,3-diol

5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-pent-1-en-3-ol

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