methyl N-[2-(N^α-benzyloxycarbonyl-N^β-tert-butoxycarbonyl-hydrazino)ethyl]-N-[(thymin-1-yl)acetyl]glycinate

Base Information

• Chemical Name: methyl N-[2-(N^α-benzyloxycarbonyl-N^β-tert-butoxycarbonyl-hydrazino)ethyl]-N-[(thymin-1-yl)acetyl]glycinate
• CAS No.: 937276-18-1
• Molecular Formula: C₂₅H₃₃N₅O₉
• Molecular Weight: 547.565

Synonyms:methyl N-[2-(N^α-benzyloxycarbonyl-N^β-tert-butoxycarbonyl-hydrazino)ethyl]-N-[(thymin-1-yl)acetyl]glycinate

Chemical Property of methyl N-[2-(N^α-benzyloxycarbonyl-N^β-tert-butoxycarbonyl-hydrazino)ethyl]-N-[(thymin-1-yl)acetyl]glycinate

Chemical Property:

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Technology Process of methyl N-[2-(N^α-benzyloxycarbonyl-N^β-tert-butoxycarbonyl-hydrazino)ethyl]-N-[(thymin-1-yl)acetyl]glycinate

There total 5 articles about methyl N-[2-(N^α-benzyloxycarbonyl-N^β-tert-butoxycarbonyl-hydrazino)ethyl]-N-[(thymin-1-yl)acetyl]glycinate 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: 75.0%

methyl N-[2-(Nα-benzyloxycarbonyl-Nβ-tert-butoxycarbonyl-hydrazino)ethyl]glycinate (937276-24-9) + thymidyl acetic acid (20924-05-4) → methyl N-[2-(Nα-benzyloxycarbonyl-Nβ-tert-butoxycarbonyl-hydrazino)ethyl]-N-[(thymin-1-yl)acetyl]glycinate (937276-18-1)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; In N,N-dimethyl-formamide; at 20 ℃; for 22h;

DOI:10.1016/j.tet.2007.02.102

Reference yield:

Nα-(benzyloxycarbonyl)-Nβ-(tert-butoxycarbonyl)-Nβ-(2-hydroxyethyl)hydrazide (937276-26-1) → methyl N-[2-(Nα-benzyloxycarbonyl-Nβ-tert-butoxycarbonyl-hydrazino)ethyl]-N-[(thymin-1-yl)acetyl]glycinate (937276-18-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Dess-Martin periodinane / CH₂Cl₂; H₂O / 0.83 h / 20 °C

1.2: methyl tert-butyl ether; NaHCO₃; Na₂S₂O₃ / CH₂Cl₂; H₂O / 0.42 h / 20 °C

2.1: 43 percent / diisopropylethylamine; NaBH₃CN; ZnCl₂ / methanol / 25 h

3.1: 75 percent / 3,4-dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine; diisopropylethylamine; N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride / dimethylformamide / 22 h / 20 °C

With sodium cyanoborohydride; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; zinc(II) chloride; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2007.02.102

Reference yield:

Nα-(benzyloxycarbonyl)-Nβ-(tert-butoxycarbonyl)-Nβ-(formylmethyl)hydrazide (937276-27-2) → methyl N-[2-(Nα-benzyloxycarbonyl-Nβ-tert-butoxycarbonyl-hydrazino)ethyl]-N-[(thymin-1-yl)acetyl]glycinate (937276-18-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 43 percent / diisopropylethylamine; NaBH₃CN; ZnCl₂ / methanol / 25 h

2: 75 percent / 3,4-dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine; diisopropylethylamine; N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride / dimethylformamide / 22 h / 20 °C

With sodium cyanoborohydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; zinc(II) chloride; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2007.02.102

upstream raw materials:

methyl N-[2-(N^α-benzyloxycarbonyl-N^β-tert-butoxycarbonyl-hydrazino)ethyl]glycinate

thymidyl acetic acid

N^α-(benzyloxycarbonyl)-N^β-(tert-butoxycarbonyl)-N^β-(2-hydroxyethyl)hydrazide

N^α-(benzyloxycarbonyl)-N^β-(tert-butoxycarbonyl)-N^β-(formylmethyl)hydrazide

Downstream raw materials:

N-[2-(N^α-benzyloxycarbonyl-N^β-tert-butoxycarbonylhydrazino)ethyl]-N-[(thymin-1-yl)acetyl]glycine

methyl N-[2-[2-(N^α-benzyloxycarbonyl-N^β-tert-butoxycarbonyl-hydrazino)ethyl]-N-[(thymin-1-yl)acetyl]glycyl]aminoethyl-N-[(thymin-1-yl)acetyl]glycinate

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