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

Base Information

• Chemical Name: methyl (1S,2R)-(-)-1-N-benzyloxycarbonylamino-2-carboxycyclopropanecarboxylate
• CAS No.: 171513-98-7
• Molecular Formula: C₁₄H₁₅NO₆
• Molecular Weight: 293.276
• Mol file: 171513-98-7.mol

Synonyms:methyl (1S,2R)-(-)-1-N-benzyloxycarbonylamino-2-carboxycyclopropanecarboxylate

Chemical Property of methyl (1S,2R)-(-)-1-N-benzyloxycarbonylamino-2-carboxycyclopropanecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (1S,2R)-(-)-1-N-benzyloxycarbonylamino-2-carboxycyclopropanecarboxylate

There total 8 articles about methyl (1S,2R)-(-)-1-N-benzyloxycarbonylamino-2-carboxycyclopropanecarboxylate 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: 62.0%

methyl (1S,2R,1'S)-(-)-1-N-benzyloxycarbonylamino-2-(1',2'-dihydroxyethyl)cyclopropanecarboxylate (160002-55-1) → methyl (1S,2R)-(-)-1-N-benzyloxycarbonylamino-2-carboxycyclopropanecarboxylate (171513-98-7)

Guidance literature:

With sodium periodate; Ru₂O hydrate; In tetrachloromethane; water; acetonitrile; for 2h; Ambient temperature;

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

Reference yield: 60.0%

methyl (1S,2R)-(-)-1-N-benzyloxycarbonylamino-2-formylcyclopropanecarboxylate (175694-63-0) → methyl (1S,2R)-(-)-1-N-benzyloxycarbonylamino-2-carboxycyclopropanecarboxylate (171513-98-7)

Guidance literature:

With dipyridinium dichromate; In N,N-dimethyl-formamide; for 36h; Ambient temperature;

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

Reference yield:

methyl (4S,2Z)-2-benzyloxycarbonylamino-4,5-isopropylidenedioxy-2-pentanoate (132970-32-2) → methyl (1S,2R)-(-)-1-N-benzyloxycarbonylamino-2-carboxycyclopropanecarboxylate (171513-98-7)

Guidance literature:

Multi-step reaction with 7 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

6: 1.) O₃, 2.) Me₂S / 1.) AcOEt, -78 deg C, 20 min, 2.) AcOEt, RT, 30 min

7: 60 percent / pyridinium dichromate / dimethylformamide / 36 h / Ambient temperature

With 1,3-dimethyl-2-phenyl-1,3,2-diazaphospholidine; hydrogenchloride; methanol; dipyridinium dichromate; benzophenone; dimethylsulfide; ozone; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

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

upstream raw materials:

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

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

N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester

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

Downstream raw materials:

(1S,2R)-1-Benzyloxycarbonylamino-2-chlorocarbonyl-cyclopropanecarboxylic acid methyl ester

(-)-(Z)-2,3-methano-L-glutamic acid

(1S,2S)-1-Benzyloxycarbonylamino-2-methoxycarbonylmethyl-cyclopropanecarboxylic acid methyl ester