(3S,7S)-7-benzyloxycarbonylamino-3-carboxy-3,7-dimethyl-1,5-diazabicyclo[4.3.0]non-5-ene

Base Information

• Chemical Name: (3S,7S)-7-benzyloxycarbonylamino-3-carboxy-3,7-dimethyl-1,5-diazabicyclo[4.3.0]non-5-ene
• CAS No.: 951172-79-5
• Molecular Formula: C₁₈H₂₃N₃O₄
• Molecular Weight: 345.398
• Mol file: 951172-79-5.mol

Synonyms:(3S,7S)-7-benzyloxycarbonylamino-3-carboxy-3,7-dimethyl-1,5-diazabicyclo[4.3.0]non-5-ene

Chemical Property of (3S,7S)-7-benzyloxycarbonylamino-3-carboxy-3,7-dimethyl-1,5-diazabicyclo[4.3.0]non-5-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,7S)-7-benzyloxycarbonylamino-3-carboxy-3,7-dimethyl-1,5-diazabicyclo[4.3.0]non-5-ene

There total 9 articles about (3S,7S)-7-benzyloxycarbonylamino-3-carboxy-3,7-dimethyl-1,5-diazabicyclo[4.3.0]non-5-ene 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: 100.0%

(3S,7S)-7-benzyloxycarbonylamino-3-methoxycarbonyl-3,7-dimethyl-1,5-diazabicyclo[4.3.0]non-5-ene (951172-78-4) → (3S,7S)-7-benzyloxycarbonylamino-3-carboxy-3,7-dimethyl-1,5-diazabicyclo[4.3.0]non-5-ene (951172-79-5)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; water; at 20 ℃; for 18h;

DOI:10.1021/jo071074x

Reference yield:

(3R)-3-benzyloxycarbonylamino-3-methyl-1-((2RS)-2-methoxycarbonyl-3-phthalimidopropyl)pyrrolidine-2-thione (951172-74-0) → (3S,7S)-7-benzyloxycarbonylamino-3-carboxy-3,7-dimethyl-1,5-diazabicyclo[4.3.0]non-5-ene (951172-79-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 68 percent / hydrazine / methanol / 24 h / 20 °C

2.1: 62 percent / HgCl₂ / dioxane / 24 h / Heating

3.1: lithium hexamethyldisilazide / tetrahydrofuran / 2 h / -78 °C

3.2: 47 percent / tetrahydrofuran / -78 - 20 °C

4.1: 100 percent / LiOH / tetrahydrofuran; methanol; H₂O / 18 h / 20 °C

With lithium hydroxide; mercury dichloride; lithium hexamethyldisilazane; hydrazine; In tetrahydrofuran; 1,4-dioxane; methanol; water;

DOI:10.1021/jo071074x

Reference yield:

methyl 3-amino-2-(phthalimidomethyl)propanoate hydrobromide → (3S,7S)-7-benzyloxycarbonylamino-3-carboxy-3,7-dimethyl-1,5-diazabicyclo[4.3.0]non-5-ene (951172-79-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 15.5 g / sodium cyanoborohydride; acetic acid / methanol / 72 h / 20 °C / pH 6

2.1: 56 percent / Lawesson's reagent / toluene / 1.5 h / Heating

3.1: 68 percent / hydrazine / methanol / 24 h / 20 °C

4.1: 62 percent / HgCl₂ / dioxane / 24 h / Heating

5.1: lithium hexamethyldisilazide / tetrahydrofuran / 2 h / -78 °C

5.2: 47 percent / tetrahydrofuran / -78 - 20 °C

6.1: 100 percent / LiOH / tetrahydrofuran; methanol; H₂O / 18 h / 20 °C

With Lawessons reagent; lithium hydroxide; sodium cyanoborohydride; acetic acid; mercury dichloride; lithium hexamethyldisilazane; hydrazine; In tetrahydrofuran; 1,4-dioxane; methanol; water; toluene;

DOI:10.1021/jo071074x

upstream raw materials:

(3S,7S)-7-benzyloxycarbonylamino-3-methoxycarbonyl-3,7-dimethyl-1,5-diazabicyclo[4.3.0]non-5-ene

(3R)-3-benzyloxycarbonylamino-3-methyl-1-((2RS)-2-methoxycarbonyl-3-phthalimidopropyl)pyrrolidine-2-thione

(3R)-3-benzyloxycarbonylamino-3-methyl-1-((2RS)-3-amino-2-methoxycarbonylpropyl)pyrrolidine-2-thione

(2S,4S)-3-benzyloxycarbonyl-4-methyl-2-phenyl-4-(prop-2-enyl)oxazolidin-5-one