(3R,4R)-4-(allyl(tert-butoxycarbonyl)amino)-5-(tert-butyldiphenylsilyloxy)pent-1-en-3-yl benzoate

Base Information

Chemical Name:(3R,4R)-4-(allyl(tert-butoxycarbonyl)amino)-5-(tert-butyldiphenylsilyloxy)pent-1-en-3-yl benzoate
CAS No.:848668-34-8
Molecular Formula:C₃₆H₄₅NO₅Si
Molecular Weight:599.842
Hs Code.:

Synonyms:(3R,4R)-4-(allyl(tert-butoxycarbonyl)amino)-5-(tert-butyldiphenylsilyloxy)pent-1-en-3-yl benzoate

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Chemical Property of (3R,4R)-4-(allyl(tert-butoxycarbonyl)amino)-5-(tert-butyldiphenylsilyloxy)pent-1-en-3-yl benzoate

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Technology Process of (3R,4R)-4-(allyl(tert-butoxycarbonyl)amino)-5-(tert-butyldiphenylsilyloxy)pent-1-en-3-yl benzoate

There total 4 articles about (3R,4R)-4-(allyl(tert-butoxycarbonyl)amino)-5-(tert-butyldiphenylsilyloxy)pent-1-en-3-yl benzoate 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: 98.0%

: 106-95-6
allyl bromide

: 848668-33-7
(3R,4R)-4-(tert-butoxycarbonylamino)-5-(tert-butyldiphenylsilyloxy)pent-1-en-3-yl benzoate

: 848668-34-8
(3R,4R)-4-(allyl(tert-butoxycarbonyl)amino)-5-(tert-butyldiphenylsilyloxy)pent-1-en-3-yl benzoate

Guidance literature:: With potassium hexamethylsilazane; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; at 0 - 20 ℃; for 5.5h;
DOI:10.1016/j.tet.2004.12.001

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 848668-34-8
(3R,4R)-4-(allyl(tert-butoxycarbonyl)amino)-5-(tert-butyldiphenylsilyloxy)pent-1-en-3-yl benzoate

Guidance literature:: Multi-step reaction with 2 steps

1: 3.96 g / NaHCO₃ / H₂O; tetrahydrofuran / 2 h / 20 °C

2: 98 percent / potassium bis(trimethylsilyl)amide / tetrahydrofuran; dimethylformamide; toluene / 5.5 h / 0 - 20 °C

With potassium hexamethylsilazane; sodium hydrogencarbonate; In tetrahydrofuran; water; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.tet.2004.12.001

Reference yield:

: (4R,5R)-4-((tert-butyldiphenylsilyloxy)methyl)-2-phenyl-5-vinyl-4,5-dihydrooxazole

: 848668-34-8
(3R,4R)-4-(allyl(tert-butoxycarbonyl)amino)-5-(tert-butyldiphenylsilyloxy)pent-1-en-3-yl benzoate

Guidance literature:: Multi-step reaction with 3 steps

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

2: 3.96 g / NaHCO₃ / H₂O; tetrahydrofuran / 2 h / 20 °C

3: 98 percent / potassium bis(trimethylsilyl)amide / tetrahydrofuran; dimethylformamide; toluene / 5.5 h / 0 - 20 °C

With hydrogenchloride; potassium hexamethylsilazane; sodium hydrogencarbonate; In tetrahydrofuran; water; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.tet.2004.12.001