N-benzyloxycarbonyl-α-(o-nitrobenzyl)-(Z)-α,β-dehydroglutanic-γ-(N-p-methoxybenzyl)hydroxamic acid

Base Information

Chemical Name:N-benzyloxycarbonyl-α-(o-nitrobenzyl)-(Z)-α,β-dehydroglutanic-γ-(N-p-methoxybenzyl)hydroxamic acid
CAS No.:104754-69-0
Molecular Formula:C₂₈H₂₇N₃O₉
Molecular Weight:549.537
Hs Code.:

Synonyms:N-benzyloxycarbonyl-α-(o-nitrobenzyl)-(Z)-α,β-dehydroglutanic-γ-(N-p-methoxybenzyl)hydroxamic acid

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Chemical Property of N-benzyloxycarbonyl-α-(o-nitrobenzyl)-(Z)-α,β-dehydroglutanic-γ-(N-p-methoxybenzyl)hydroxamic acid

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Technology Process of N-benzyloxycarbonyl-α-(o-nitrobenzyl)-(Z)-α,β-dehydroglutanic-γ-(N-p-methoxybenzyl)hydroxamic acid

There total 10 articles about N-benzyloxycarbonyl-α-(o-nitrobenzyl)-(Z)-α,β-dehydroglutanic-γ-(N-p-methoxybenzyl)hydroxamic acid 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:

: 3717-21-3,3717-22-4,140461-28-5,140461-29-6,3235-04-9
p-methoxyl benzaldoxime

: 104754-69-0
N-benzyloxycarbonyl-α-(o-nitrobenzyl)-(Z)-α,β-dehydroglutanic-γ-(N-p-methoxybenzyl)hydroxamic acid

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) NaBH₃CN, 2.) imidazole / 1.) MeOH, pH 3, 2.) DMF

2: 1.) DCC, N-hydroxysuccinimide, 2.) anhydrous KF / 1.) THF, 2.) EtOH

With 1H-imidazole; potassium fluoride; 1-hydroxy-pyrrolidine-2,5-dione; sodium cyanoborohydride; dicyclohexyl-carbodiimide;
DOI:10.1021/ja00394a039

Reference yield:

: 76843-80-6
O-(t-butyldimethylsilyl)-N-(p-methoxybenzyl)-hydroxylamine

: 105933-67-3
N-benzyloxycarbonyl-α-(o-nitrobenzyl)-(Z)-α,β-dehydroglutamate

: 104754-69-0
N-benzyloxycarbonyl-α-(o-nitrobenzyl)-(Z)-α,β-dehydroglutanic-γ-(N-p-methoxybenzyl)hydroxamic acid

Guidance literature:: With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide; Yield given. Multistep reaction; 1.) THF, 15 min, 2.) RT, 3 days;
DOI:10.1016/S0040-4020(01)96774-2

Reference yield:

: 621-84-1
O-benzyl carbamate

: 104754-69-0
N-benzyloxycarbonyl-α-(o-nitrobenzyl)-(Z)-α,β-dehydroglutanic-γ-(N-p-methoxybenzyl)hydroxamic acid

Guidance literature:: Multi-step reaction with 4 steps

1: 71 percent / 4 h / 80 °C / 10 - 15 Torr

2: 89 percent / Et₃N / ethyl acetate / 4 h / Heating

3: 100 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene (DBU) / tetrahydrofuran / 0.5 h / 0 °C

4: 1.) N-hydroxysuccinimide, N,N-dicyclohexylcarbodiimide (DCC) / 1.) THF, 15 min, 2.) RT, 3 days

With 1-hydroxy-pyrrolidine-2,5-dione; triethylamine; dicyclohexyl-carbodiimide; 1,5-Diazabicyclo[5.4.0]undec-5-ene; In tetrahydrofuran; ethyl acetate;
DOI:10.1016/S0040-4020(01)96774-2