tert-butyl 7-(N³-benzoyluracil-1-yl)-5S-[N-(tert-butoxycarbonyl)amino]-3-oxaheptanate

Base Information

• Chemical Name: tert-butyl 7-(N³-benzoyluracil-1-yl)-5S-[N-(tert-butoxycarbonyl)amino]-3-oxaheptanate
• CAS No.: 191655-65-9
• Molecular Formula: C₂₆H₃₅N₃O₈
• Molecular Weight: 517.579

Synonyms:tert-butyl 7-(N³-benzoyluracil-1-yl)-5S-[N-(tert-butoxycarbonyl)amino]-3-oxaheptanate

Chemical Property of tert-butyl 7-(N³-benzoyluracil-1-yl)-5S-[N-(tert-butoxycarbonyl)amino]-3-oxaheptanate

Chemical Property:

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Technology Process of tert-butyl 7-(N³-benzoyluracil-1-yl)-5S-[N-(tert-butoxycarbonyl)amino]-3-oxaheptanate

There total 13 articles about tert-butyl 7-(N³-benzoyluracil-1-yl)-5S-[N-(tert-butoxycarbonyl)amino]-3-oxaheptanate 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: 76.0%

3-N-benzoyluracil (2775-87-3) + tert-butyl 7-hydroxy-5S-[N-(tert-butoxycarbonyl)amino]-3-oxaheptanate (220418-65-5) → tert-butyl 7-(N3-benzoyluracil-1-yl)-5S-[N-(tert-butoxycarbonyl)amino]-3-oxaheptanate (191655-65-9)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 20 ℃; for 2h;

DOI:10.1016/S0960-894X(97)00172-8

Reference yield:

(2S)-2-tert-butoxycarbonylamino-4-(tert-butyldimethyl-silanyloxy)-butyric acid benzyl ester (191655-44-4) → tert-butyl 7-(N3-benzoyluracil-1-yl)-5S-[N-(tert-butoxycarbonyl)amino]-3-oxaheptanate (191655-65-9)

Guidance literature:

Multi-step reaction with 6 steps

1: H₂ / 10percent Pd-C

2: N-methylmorpholine / 1,2-dimethoxy-ethane

3: NaBH₄ / H₂O

4: 89 percent / Bu₄NHSO₄, aq. NaOH / benzene; H₂O / 21 h / 10 °C

5: 89 percent / TBAF / tetrahydrofuran / 0.5 h / Ambient temperature

6: 76 percent / DEAD, Ph₃P / tetrahydrofuran / 2 h / 0 - 20 °C

With 4-methyl-morpholine; sodium hydroxide; sodium tetrahydroborate; tetrabutyl ammonium fluoride; hydrogen; tetra(n-butyl)ammonium hydrogensulfate; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; 1,2-dimethoxyethane; water; benzene;

DOI:10.1016/S0960-894X(97)00172-8

Reference yield:

bromoacetic acid tert-butyl ester (5292-43-3) → tert-butyl 7-(N3-benzoyluracil-1-yl)-5S-[N-(tert-butoxycarbonyl)amino]-3-oxaheptanate (191655-65-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 30 percent / NaH / tetrahydrofuran

2: pyridinium p-toluenesulfonate / ethanol

3: 46 percent / diethyl azodicarboxylate; PPh₃ / tetrahydrofuran / 20 h / 20 °C

With pyridinium p-toluenesulfonate; sodium hydride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; ethanol; 1: Alkylation / 2: Hydrolysis / 3: Substitution;

DOI:10.1016/S0040-4020(99)00541-4

upstream raw materials:

3-N-benzoyluracil

tert-butyl 7-hydroxy-5S-[N-(tert-butoxycarbonyl)amino]-3-oxaheptanate

bromoacetic acid tert-butyl ester

di-tert-butyl dicarbonate

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