N^α-(benzyloxycarbonyl)-N^β-(tert-butoxycarbonyl)-N^β-methyl-L-α,β-diaminopropionylglycyl-N⁵,N⁸-bis(tert-butoxycarbonyl)spermidine

Base Information

• Chemical Name: N^α-(benzyloxycarbonyl)-N^β-(tert-butoxycarbonyl)-N^β-methyl-L-α,β-diaminopropionylglycyl-N⁵,N⁸-bis(tert-butoxycarbonyl)spermidine
• CAS No.: 138093-86-4
• Molecular Formula: C₃₆H₆₀N₆O₁₀
• Molecular Weight: 736.907

Synonyms:N^α-(benzyloxycarbonyl)-N^β-(tert-butoxycarbonyl)-N^β-methyl-L-α,β-diaminopropionylglycyl-N⁵,N⁸-bis(tert-butoxycarbonyl)spermidine

Chemical Property of N^α-(benzyloxycarbonyl)-N^β-(tert-butoxycarbonyl)-N^β-methyl-L-α,β-diaminopropionylglycyl-N⁵,N⁸-bis(tert-butoxycarbonyl)spermidine

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of N^α-(benzyloxycarbonyl)-N^β-(tert-butoxycarbonyl)-N^β-methyl-L-α,β-diaminopropionylglycyl-N⁵,N⁸-bis(tert-butoxycarbonyl)spermidine

There total 21 articles about N^α-(benzyloxycarbonyl)-N^β-(tert-butoxycarbonyl)-N^β-methyl-L-α,β-diaminopropionylglycyl-N⁵,N⁸-bis(tert-butoxycarbonyl)spermidine 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: 72.0%

C19H27N3O7 + N,N-bis(tert-butoxycarbonyl)spermidine (85503-20-4) → Nα-(benzyloxycarbonyl)-Nβ-(tert-butoxycarbonyl)-Nβ-methyl-L-α,β-diaminopropionylglycyl-N5,N8-bis(tert-butoxycarbonyl)spermidine (138093-86-4)

Guidance literature:

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 24h;

DOI:10.1021/jacs.1c09616

Reference yield:

10-<(1,1-dimethylethoxy)carbonyl>-4-oxo-2,5,10,14-tetraazapentadecanedioic acid, 1-phenylmethyl 15-(1,1-dimethylethyl) ester (130619-30-6) → Nα-(benzyloxycarbonyl)-Nβ-(tert-butoxycarbonyl)-Nβ-methyl-L-α,β-diaminopropionylglycyl-N5,N8-bis(tert-butoxycarbonyl)spermidine (138093-86-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / H₂ / 10percent Pd/C / methanol / 14 h / 760 Torr / Ambient temperature

2: 62 percent / diethyl phosphorocyanidate (DEPC), Et₃N / dimethylformamide / 4 h / 0 °C

With diethyl cyanophosphonate; hydrogen; triethylamine; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/ja00029a031

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → Nα-(benzyloxycarbonyl)-Nβ-(tert-butoxycarbonyl)-Nβ-methyl-L-α,β-diaminopropionylglycyl-N5,N8-bis(tert-butoxycarbonyl)spermidine (138093-86-4)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

2: 1N NaOH / tetrahydrofuran / 14 h / 0 °C

3: 62 percent / diethyl phosphorocyanidate (DEPC), Et₃N / dimethylformamide / 4 h / 0 °C

With sodium hydroxide; diethyl cyanophosphonate; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00029a031

upstream raw materials:

di-tert-butyl dicarbonate

N-[(benzyloxy)carbonyl]-3-[(tert-butoxycarbonyl)amino]-L-alanine

methyl (2S)-2-{[(benzyloxy)carbonyl]amino}-3-[(tert-butoxycarbonyl)amino]propanoate

10-<(1,1-dimethylethoxy)carbonyl>-4-oxo-2,5,10,14-tetraazapentadecanedioic acid, 1-phenylmethyl 15-(1,1-dimethylethyl) ester

Downstream raw materials:

N-(benzyloxycarbonyl)-5,7-isopropylidenegalantinyl-N^β-(tert-butoxycarbonyl)-N^β-methyl-L-α,β-diaminopropionylglycyl-N⁵,N⁸-bis(tert-butoxycarbonyl)spermidine

3-epi-N-(benzyloxycarbonyl)-5,7-isopropylidenegalantinyl-N^β-(tert-butoxycarbonyl)-N^β-methyl-L-α,β-diaminopropionylglycyl-N⁵,N⁸-bis(tert-butoxycarbonyl)spermidine

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