tert-butyl (1S,3S,4S,5S,6R)-2-[(2S)-2-benzyloxycarbonylamino-3-tert-butoxycarbonylpropionyl]-5,6-dihydroxy-2-azabicyclo[2.2.1]heptane-3-carboxylate

Base Information

• Chemical Name: tert-butyl (1S,3S,4S,5S,6R)-2-[(2S)-2-benzyloxycarbonylamino-3-tert-butoxycarbonylpropionyl]-5,6-dihydroxy-2-azabicyclo[2.2.1]heptane-3-carboxylate
• CAS No.: 697289-82-0
• Molecular Formula: C₂₇H₃₈N₂O₉
• Molecular Weight: 534.607

Synonyms:tert-butyl (1S,3S,4S,5S,6R)-2-[(2S)-2-benzyloxycarbonylamino-3-tert-butoxycarbonylpropionyl]-5,6-dihydroxy-2-azabicyclo[2.2.1]heptane-3-carboxylate

Chemical Property of tert-butyl (1S,3S,4S,5S,6R)-2-[(2S)-2-benzyloxycarbonylamino-3-tert-butoxycarbonylpropionyl]-5,6-dihydroxy-2-azabicyclo[2.2.1]heptane-3-carboxylate

Chemical Property:

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Technology Process of tert-butyl (1S,3S,4S,5S,6R)-2-[(2S)-2-benzyloxycarbonylamino-3-tert-butoxycarbonylpropionyl]-5,6-dihydroxy-2-azabicyclo[2.2.1]heptane-3-carboxylate

There total 3 articles about tert-butyl (1S,3S,4S,5S,6R)-2-[(2S)-2-benzyloxycarbonylamino-3-tert-butoxycarbonylpropionyl]-5,6-dihydroxy-2-azabicyclo[2.2.1]heptane-3-carboxylate 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%

Z-D(tBu)-OH (5545-52-8) + (1S,3S,4S,5S,6R)-5,6-dihydroxy-2-azabicyclo[2.2.1]heptane-3-carboxylic acid tert-butyl ester (697290-66-7) → tert-butyl (1S,3S,4S,5S,6R)-2-[(2S)-2-benzyloxycarbonylamino-3-tert-butoxycarbonylpropionyl]-5,6-dihydroxy-2-azabicyclo[2.2.1]heptane-3-carboxylate (697289-82-0)

Guidance literature:

With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1002/ejoc.200300700

Reference yield:

(1S,3S,4R)-2-[(1R)-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylic acid tert-butyl ester (697289-60-4) → tert-butyl (1S,3S,4S,5S,6R)-2-[(2S)-2-benzyloxycarbonylamino-3-tert-butoxycarbonylpropionyl]-5,6-dihydroxy-2-azabicyclo[2.2.1]heptane-3-carboxylate (697289-82-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 65 percent / KMnO₄; NaOH / 2-methyl-propan-2-ol; H₂O / 0.25 h / 0 °C

2: 70 percent / H₂ / Pd/C / methanol / 24 h / 20 °C / 760 Torr

3: 72 percent / HOBt; DCC / dimethylformamide / 12 h / 20 °C

With sodium hydroxide; potassium permanganate; hydrogen; benzotriazol-1-ol; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1002/ejoc.200300700

Reference yield:

(1S,3S,4S,5S,6R)-5,6-Dihydroxy-2-((R)-1-phenyl-ethyl)-2-aza-bicyclo[2.2.1]heptane-3-carboxylic acid tert-butyl ester → tert-butyl (1S,3S,4S,5S,6R)-2-[(2S)-2-benzyloxycarbonylamino-3-tert-butoxycarbonylpropionyl]-5,6-dihydroxy-2-azabicyclo[2.2.1]heptane-3-carboxylate (697289-82-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / H₂ / Pd/C / methanol / 24 h / 20 °C / 760 Torr

2: 72 percent / HOBt; DCC / dimethylformamide / 12 h / 20 °C

With hydrogen; benzotriazol-1-ol; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200300700

upstream raw materials:

Z-D(tBu)-OH

(1S,3S,4S,5S,6R)-5,6-dihydroxy-2-azabicyclo[2.2.1]heptane-3-carboxylic acid tert-butyl ester

(1S,3S,4R)-2-[(1R)-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylic acid tert-butyl ester

Downstream raw materials:

2-benzoyl-7-(2-tert-butoxycarbonyl-ethyl)-3-tert-butoxycarbonylmethyl-4-oxo-octahydro-pyrrolo[1,2-a]pyrazine-6-carboxylic acid tert-butyl ester

3-tert-butoxycarbonylmethyl-1-hydroxy-4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6,7-tricarboxylic acid 2-benzyl ester 6-tert-butyl ester

3-tert-butoxycarbonylmethyl-7-formyl-1-hydroxy-4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-tert-butyl ester

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