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

Base Information

• Chemical Name: methyl (1S,2R,4'S)-(-)-1-N-benzyloxycarbonylamino-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclopropanecarboxylate
• CAS No.: 160002-54-0
• Molecular Formula: C₁₈H₂₃NO₆
• Molecular Weight: 349.384
• Mol file: 160002-54-0.mol

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

Chemical Property of methyl (1S,2R,4'S)-(-)-1-N-benzyloxycarbonylamino-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclopropanecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (1S,2R,4'S)-(-)-1-N-benzyloxycarbonylamino-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclopropanecarboxylate

There total 6 articles about methyl (1S,2R,4'S)-(-)-1-N-benzyloxycarbonylamino-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclopropanecarboxylate 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%

methyl (3R,4R,4'S)-(-)-3-N-benzyloxycarbonylamino-4-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-1-pyrazoline-3-carboxylate (160002-53-9) → methyl (1S,2R,4'S)-(-)-1-N-benzyloxycarbonylamino-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclopropanecarboxylate (160002-54-0)

Guidance literature:

With benzophenone; In dichloromethane; at -78 ℃; for 0.3h;

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

Reference yield: 5.0%

methyl (3R,4R,4'S)-(-)-3-N-benzyloxycarbonylamino-4-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-1-pyrazoline-3-carboxylate (160002-53-9) → methyl (1S,2R,4'S)-(-)-1-N-benzyloxycarbonylamino-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclopropanecarboxylate (160002-54-0) + methyl (Z)-(4'S)--3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)butenoate

Guidance literature:

In toluene; at -78 ℃; for 5h; Irradiation;

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

Reference yield:

methyl (4S,2Z)-2-benzyloxycarbonylamino-4,5-isopropylidenedioxy-2-pentanoate (132970-32-2) → methyl (1S,2R,4'S)-(-)-1-N-benzyloxycarbonylamino-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclopropanecarboxylate (160002-54-0)

Guidance literature:

Multi-step reaction with 2 steps

1: diethyl ether / Ambient temperature

2: 100 percent / benzophenone / CH₂Cl₂ / 0.22 h / -78 °C / rate constants for decay of pyrazoline transients for title compound

With benzophenone; In diethyl ether; dichloromethane;

DOI:10.1016/S0040-4020(97)00098-7

upstream raw materials:

methyl (3R,4R,4'S)-(-)-3-N-benzyloxycarbonylamino-4-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-1-pyrazoline-3-carboxylate

diazomethane

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

N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester

Downstream raw materials:

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

methyl (1S,2R)-(-)-1-N-benzyloxycarbonylamino-2-methanesulfonyloxymethylcyclopropanecarboxylate

methyl (1S,2R)-(+)-1-N-benzyloxycarbonylamino-2-methylthiomethylcyclopropanecarboxylate

methyl (1S,2R)-(-)-1-N-benzyloxycarbonylamino-2-formylcyclopropanecarboxylate