(2R,3R,4R,6E)-2-tert-butoxycarbonylamino-3-benzoyloxy-1-tert-butyldimethylsilyloxy-4-methyloct-6-ene

Base Information

Chemical Name:(2R,3R,4R,6E)-2-tert-butoxycarbonylamino-3-benzoyloxy-1-tert-butyldimethylsilyloxy-4-methyloct-6-ene
CAS No.:372119-47-6
Molecular Formula:C₂₇H₄₅NO₅Si
Molecular Weight:491.744
Hs Code.:

Synonyms:(2R,3R,4R,6E)-2-tert-butoxycarbonylamino-3-benzoyloxy-1-tert-butyldimethylsilyloxy-4-methyloct-6-ene

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Chemical Property of (2R,3R,4R,6E)-2-tert-butoxycarbonylamino-3-benzoyloxy-1-tert-butyldimethylsilyloxy-4-methyloct-6-ene

Chemical Property:

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Technology Process of (2R,3R,4R,6E)-2-tert-butoxycarbonylamino-3-benzoyloxy-1-tert-butyldimethylsilyloxy-4-methyloct-6-ene

There total 9 articles about (2R,3R,4R,6E)-2-tert-butoxycarbonylamino-3-benzoyloxy-1-tert-butyldimethylsilyloxy-4-methyloct-6-ene 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: 90.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 372119-46-5
(2R,3R,4R,6E)-2-tert-butoxycarbonylamino-3-benzoyloxy-4-methyloct-6-en-1-ol

: 372119-47-6
(2R,3R,4R,6E)-2-tert-butoxycarbonylamino-3-benzoyloxy-1-tert-butyldimethylsilyloxy-4-methyloct-6-ene

Guidance literature:: With 1H-imidazole; In dichloromethane; at 10 ℃; for 2h;
DOI:10.1021/jo015760m

Reference yield:

: 4-(tert-butyl-dimethyl-silanyloxymethyl)-5-isopropenyl-oxazolidin-2-one

: 372119-47-6
(2R,3R,4R,6E)-2-tert-butoxycarbonylamino-3-benzoyloxy-1-tert-butyldimethylsilyloxy-4-methyloct-6-ene

Guidance literature:: Multi-step reaction with 8 steps

1: NaH / tetrahydrofuran / 0 - 20 °C

2: 1,3-bis(diphenylphosphino)propane / Pd₂(dibenzylideneacetone)3CHCl₃ / tetrahydrofuran / 4 h / 50 °C

3: tetrahydrofuran / 0 - 20 °C

4: 1.53 g / aq. NaOH; Pd(PPh₃)4 / tetrahydrofuran / 4 h / 55 - 60 °C

5: 90 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

6: aq. HCl / tetrahydrofuran / 16 h / 20 °C

7: 271 mg / NaHCO₃ / H₂O; tetrahydrofuran / 2 h / 20 °C

8: 90 percent / imidazole / CH₂Cl₂ / 2 h / 10 °C

With 1H-imidazole; hydrogenchloride; sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,3-bis-(diphenylphosphino)propane; tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; dichloromethane; water; 4: Suzuki coupling;
DOI:10.1021/jo015760m

Reference yield:

: (4R)-4-tert-butoxycarbonylamino-5-tert-butyldimethylsilyloxy-2-methylpent-1-en-3-ol

: 372119-47-6
(2R,3R,4R,6E)-2-tert-butoxycarbonylamino-3-benzoyloxy-1-tert-butyldimethylsilyloxy-4-methyloct-6-ene

Guidance literature:: Multi-step reaction with 9 steps

1: NaH / tetrahydrofuran / 0 - 20 °C

2: NaH / tetrahydrofuran / 0 - 20 °C

3: 1,3-bis(diphenylphosphino)propane / Pd₂(dibenzylideneacetone)3CHCl₃ / tetrahydrofuran / 4 h / 50 °C

4: tetrahydrofuran / 0 - 20 °C

5: 1.53 g / aq. NaOH; Pd(PPh₃)4 / tetrahydrofuran / 4 h / 55 - 60 °C

6: 90 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

7: aq. HCl / tetrahydrofuran / 16 h / 20 °C

8: 271 mg / NaHCO₃ / H₂O; tetrahydrofuran / 2 h / 20 °C

9: 90 percent / imidazole / CH₂Cl₂ / 2 h / 10 °C

With 1H-imidazole; hydrogenchloride; sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,3-bis-(diphenylphosphino)propane; tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; dichloromethane; water; 5: Suzuki coupling;
DOI:10.1021/jo015760m