(+)-N-benzyloxycarbonyl-γ,δ-dehydro-allo-coronamic acid methyl ester

Base Information

• Chemical Name: (+)-N-benzyloxycarbonyl-γ,δ-dehydro-allo-coronamic acid methyl ester
• CAS No.: 160002-57-3
• Molecular Formula: C₁₅H₁₇NO₄
• Molecular Weight: 275.304
• Mol file: 160002-57-3.mol

Synonyms:(+)-N-benzyloxycarbonyl-γ,δ-dehydro-allo-coronamic acid methyl ester

Chemical Property of (+)-N-benzyloxycarbonyl-γ,δ-dehydro-allo-coronamic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-N-benzyloxycarbonyl-γ,δ-dehydro-allo-coronamic acid methyl ester

There total 6 articles about (+)-N-benzyloxycarbonyl-γ,δ-dehydro-allo-coronamic acid methyl ester 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: 90.0%

methyl (1S,2R,4'S)-(-)-1-N-benzyloxycarbonylamino-2-(1',3'-dioxolan-2'-thiocarbonyl-4'-yl)cyclopropanecarboxylate (160002-56-2) → (+)-N-benzyloxycarbonyl-γ,δ-dehydro-allo-coronamic acid methyl ester (160002-57-3)

Guidance literature:

With 1,3-dimethyl-2-phenyl-1,3,2-diazaphospholidine; In tetrahydrofuran; at 50 ℃; for 20h;

DOI:10.1016/S0040-4039(00)78226-8

Reference yield:

methyl (4S,2Z)-2-benzyloxycarbonylamino-4,5-isopropylidenedioxy-2-pentanoate (132970-32-2) → (+)-N-benzyloxycarbonyl-γ,δ-dehydro-allo-coronamic acid methyl ester (160002-57-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / diethyl ether / 4 h / Ambient temperature

2: 100 percent / benzophenone / CH₂Cl₂ / 0.3 h / -78 °C

3: 100 percent / 5percent HCl/MeOH / 2.5 h / Ambient temperature

4: 90 percent / tetrahydrofuran / 6 h / Heating

5: 90 percent / 1,3-dimethyl-2-phenyl-1,3,2-diazaphospholidine / 20 h / 40 °C

With 1,3-dimethyl-2-phenyl-1,3,2-diazaphospholidine; hydrogenchloride; methanol; benzophenone; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1016/0957-4166(96)00038-9

Reference yield:

methyl (1S,2R,4'S)-(-)-1-N-benzyloxycarbonylamino-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclopropanecarboxylate (160002-54-0) → (+)-N-benzyloxycarbonyl-γ,δ-dehydro-allo-coronamic acid methyl ester (160002-57-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / 5percent HCl/MeOH / 2.5 h / Ambient temperature

2: 90 percent / tetrahydrofuran / 6 h / Heating

3: 90 percent / 1,3-dimethyl-2-phenyl-1,3,2-diazaphospholidine / 20 h / 40 °C

With 1,3-dimethyl-2-phenyl-1,3,2-diazaphospholidine; hydrogenchloride; methanol; In tetrahydrofuran;

DOI:10.1016/0957-4166(96)00038-9

upstream raw materials:

methyl (1S,2R,4'S)-(-)-1-N-benzyloxycarbonylamino-2-(1',3'-dioxolan-2'-thiocarbonyl-4'-yl)cyclopropanecarboxylate

methyl (1S,2R,1'S)-(-)-1-N-benzyloxycarbonylamino-2-(1',2'-dihydroxyethyl)cyclopropanecarboxylate

N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester

methyl (4S,2Z)-2-benzyloxycarbonylamino-4,5-isopropylidenedioxy-2-pentanoate

Downstream raw materials:

methyl (RS)-N-(benzyloxycarbonyl)-2-amino-4-pentenoate

(+)-(1S,2R)-allocoronamic acid

(-)-(Z)-2,3-methanomethionine

(1S,2R)-1-benzyloxycarbonylamino-2-chloromethyl-1-cyclopropanecarboxylic acid methyl ester