methyl 2-benzyloxycarbonylamino-(1R,2S)-cyclobutane-1-carboxylate

Base Information

• Chemical Name: methyl 2-benzyloxycarbonylamino-(1R,2S)-cyclobutane-1-carboxylate
• CAS No.: 221158-91-4
• Molecular Formula: C₁₄H₁₇NO₄
• Molecular Weight: 263.293
• Mol file: 221158-91-4.mol

Synonyms:methyl 2-benzyloxycarbonylamino-(1R,2S)-cyclobutane-1-carboxylate

Chemical Property of methyl 2-benzyloxycarbonylamino-(1R,2S)-cyclobutane-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-benzyloxycarbonylamino-(1R,2S)-cyclobutane-1-carboxylate

There total 6 articles about methyl 2-benzyloxycarbonylamino-(1R,2S)-cyclobutane-1-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:

2-benzyloxycarbonylamino-(1R,2S)-cyclobutane-1-carboxylic acid (221158-93-6) + methyl iodide (74-88-4) → methyl 2-benzyloxycarbonylamino-(1R,2S)-cyclobutane-1-carboxylate (221158-91-4)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃;

Reference yield:

(1S,2R)-cis-2-methoxycarbonyl-cyclobutane-1-carboxylic acid (88335-88-0) → methyl 2-benzyloxycarbonylamino-(1R,2S)-cyclobutane-1-carboxylate (221158-91-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: ethyl chloroformate; Et₃N / acetone / 2 h / 0 °C

1.2: 90 percent / aq. NaN₃ / acetone / 1.5 h / 20 °C

2.1: 3 h / 50 °C

With chloroformic acid ethyl ester; triethylamine; In acetone; 1.1: Acylation / 1.2: Substitution / 2.1: Curtius rearrangement;

DOI:10.1016/S0957-4166(00)00297-4

Reference yield:

dimethyl cis-1,2-cyclobutanedicarboxylate (2607-03-6) → methyl 2-benzyloxycarbonylamino-(1R,2S)-cyclobutane-1-carboxylate (221158-91-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / H₂O, pig liver esterase

2: Et₃N

3: NaN₃

4: toluene / Heating

With sodium azide; pig liver esterase; water; triethylamine; In toluene;

DOI:10.1016/S0957-4166(98)00462-5

upstream raw materials:

methyl 2-azidocarbonyl-(1R,2S)-cyclobutane-1-carboxylate

benzyl alcohol

(1S,2R)-cis-2-methoxycarbonyl-cyclobutane-1-carboxylic acid

dimethyl cis-1,2-cyclobutanedicarboxylate

Downstream raw materials:

benzyl N-[(1S,2S)-2-(pyrrolidinylmethyl)cyclobutyl]carbamate

[(1R,2S)-2-(benzyloxycarbonylamino)cyclobutyl]methyl methanesulfonate

benzyl N-[(1S,2R)-2-(hydroxymethyl)cyclobutyl]carbamate

1-[3,5-bis(trifluoromethyl)phenyl]-3-[(1S,2S)-2-(pyrrolidinylmethyl)cyclobutyl]thiourea