(2S,3R,20Z)-1-tert-butyldiphenylsilyloxy-2,3-epoxy-20-octacosene

Base Information

• Chemical Name: (2S,3R,20Z)-1-tert-butyldiphenylsilyloxy-2,3-epoxy-20-octacosene
• CAS No.: 159627-76-6
• Molecular Formula: C₄₄H₇₂O₂Si
• Molecular Weight: 661.14

Synonyms:

Chemical Property of (2S,3R,20Z)-1-tert-butyldiphenylsilyloxy-2,3-epoxy-20-octacosene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,20Z)-1-tert-butyldiphenylsilyloxy-2,3-epoxy-20-octacosene

There total 14 articles about (2S,3R,20Z)-1-tert-butyldiphenylsilyloxy-2,3-epoxy-20-octacosene 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:

13-bromo-1-tridecylalcohol (116754-58-6) → (2S,3R,20Z)-1-tert-butyldiphenylsilyloxy-2,3-epoxy-20-octacosene (159627-76-6)

Guidance literature:

Multi-step reaction with 12 steps

1: 98 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 4 h / Ambient temperature

2: 91 percent / xylene; tetrahydrofuran; hexamethylphosphoric acid triamide / 36 h / Ambient temperature

3: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h

4: 99 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature

5: 92 percent / 1,3-propanediamine, Li, potassium tert-butoxide / 2 h / Ambient temperature

6: 98 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 4 h / Ambient temperature

7: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h

8: 94 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature

9: 93 percent / H₂, quinoline / Lindlar palladium catalyst / hexane / 20.5 h / Ambient temperature

10: 95 percent / Et₃N, DMAP / CH₂Cl₂ / 6 h / Ambient temperature

11: 97 percent / LiBr, NaHCO₃ / acetone / 15 h / Ambient temperature

12: 1.) Mg, 2.) CuI / 1.) ether, r.t., 2 h, 2.) ether, HMPA, r.t., 18 h

With quinoline; dmap; copper(l) iodide; n-butyllithium; potassium tert-butylate; hydrogen; pyridinium p-toluenesulfonate; lithium; sodium hydrogencarbonate; toluene-4-sulfonic acid; magnesium; Trimethylenediamine; triethylamine; lithium bromide; Lindlar's catalyst; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; acetone; xylene;

Reference yield:

1,13-tridecanediol (13362-52-2) → (2S,3R,20Z)-1-tert-butyldiphenylsilyloxy-2,3-epoxy-20-octacosene (159627-76-6)

Guidance literature:

Multi-step reaction with 13 steps

1: 72 percent / 48percent HBr / benzene / 36 h / Heating

2: 98 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 4 h / Ambient temperature

3: 91 percent / xylene; tetrahydrofuran; hexamethylphosphoric acid triamide / 36 h / Ambient temperature

4: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h

5: 99 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature

6: 92 percent / 1,3-propanediamine, Li, potassium tert-butoxide / 2 h / Ambient temperature

7: 98 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 4 h / Ambient temperature

8: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h

9: 94 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature

10: 93 percent / H₂, quinoline / Lindlar palladium catalyst / hexane / 20.5 h / Ambient temperature

11: 95 percent / Et₃N, DMAP / CH₂Cl₂ / 6 h / Ambient temperature

12: 97 percent / LiBr, NaHCO₃ / acetone / 15 h / Ambient temperature

13: 1.) Mg, 2.) CuI / 1.) ether, r.t., 2 h, 2.) ether, HMPA, r.t., 18 h

With quinoline; dmap; copper(l) iodide; n-butyllithium; potassium tert-butylate; hydrogen bromide; hydrogen; pyridinium p-toluenesulfonate; lithium; sodium hydrogencarbonate; toluene-4-sulfonic acid; magnesium; Trimethylenediamine; triethylamine; lithium bromide; Lindlar's catalyst; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; acetone; xylene; benzene;

Reference yield:

1,4-dioxa-cycloheptadecane-5,17-dione (105-95-3,91462-25-8) → (2S,3R,20Z)-1-tert-butyldiphenylsilyloxy-2,3-epoxy-20-octacosene (159627-76-6)

Guidance literature:

Multi-step reaction with 14 steps

1: 98 percent / LiAlH₄ / diethyl ether / 3.5 h / Ambient temperature

2: 72 percent / 48percent HBr / benzene / 36 h / Heating

3: 98 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 4 h / Ambient temperature

4: 91 percent / xylene; tetrahydrofuran; hexamethylphosphoric acid triamide / 36 h / Ambient temperature

5: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h

6: 99 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature

7: 92 percent / 1,3-propanediamine, Li, potassium tert-butoxide / 2 h / Ambient temperature

8: 98 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 4 h / Ambient temperature

9: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h

10: 94 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature

11: 93 percent / H₂, quinoline / Lindlar palladium catalyst / hexane / 20.5 h / Ambient temperature

12: 95 percent / Et₃N, DMAP / CH₂Cl₂ / 6 h / Ambient temperature

13: 97 percent / LiBr, NaHCO₃ / acetone / 15 h / Ambient temperature

14: 1.) Mg, 2.) CuI / 1.) ether, r.t., 2 h, 2.) ether, HMPA, r.t., 18 h

With quinoline; dmap; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; potassium tert-butylate; hydrogen bromide; hydrogen; pyridinium p-toluenesulfonate; lithium; sodium hydrogencarbonate; toluene-4-sulfonic acid; magnesium; Trimethylenediamine; triethylamine; lithium bromide; Lindlar's catalyst; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; acetone; xylene; benzene;

upstream raw materials:

(2R,3S)-4-tert-Butyldiphenylsilyloxy-2,3-epoxybutyl tosylate

(Z)-16-tetracosenyl bromide

1,13-tridecanediol

13-bromo-1-tridecylalcohol

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