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

Base Information

Chemical Name:methyl (1S,2R)-(+)-1-N-benzyloxycarbonylamino-2-iodomethylcyclopropanecarboxylate
CAS No.:175694-68-5
Molecular Formula:C₁₄H₁₆INO₄
Molecular Weight:389.19
Hs Code.:

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

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

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

There total 10 articles about methyl (1S,2R)-(+)-1-N-benzyloxycarbonylamino-2-iodomethylcyclopropanecarboxylate 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: 89.0%

: 175694-64-1
methyl (1S,2R)-(-)-1-N-benzyloxycarbonylamino-2-methanesulfonyloxymethylcyclopropanecarboxylate

: 175694-68-5
methyl (1S,2R)-(+)-1-N-benzyloxycarbonylamino-2-iodomethylcyclopropanecarboxylate

Guidance literature:: With sodium iodide; In acetone; at 0 ℃; for 3h;
DOI:10.1016/0957-4166(96)00038-9

Reference yield:

: 100945-15-1,88568-95-0
N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester

: 175694-68-5
methyl (1S,2R)-(+)-1-N-benzyloxycarbonylamino-2-iodomethylcyclopropanecarboxylate

Guidance literature:: Multi-step reaction with 10 steps

1: 85 percent / t-BuOK

2: 100 percent / diethyl ether / 4 h / Ambient temperature

3: 100 percent / benzophenone / CH₂Cl₂ / 0.3 h / -78 °C

4: 100 percent / 5percent HCl/MeOH / 2.5 h / Ambient temperature

5: 90 percent / tetrahydrofuran / 6 h / Heating

6: 90 percent / 1,3-dimethyl-2-phenyl-1,3,2-diazaphospholidine / 20 h / 40 °C

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

8: 87 percent / NaBH₄ / methanol / 0.33 h / 0 °C

9: 96 percent / Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

10: 89 percent / NaI / acetone / 3 h / 0 °C

With 1,3-dimethyl-2-phenyl-1,3,2-diazaphospholidine; hydrogenchloride; methanol; sodium tetrahydroborate; benzophenone; dimethylsulfide; potassium tert-butylate; ozone; triethylamine; sodium iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetone;
DOI:10.1016/0957-4166(96)00038-9

Reference yield:

: 132970-32-2
methyl (4S,2Z)-2-benzyloxycarbonylamino-4,5-isopropylidenedioxy-2-pentanoate

: 175694-68-5
methyl (1S,2R)-(+)-1-N-benzyloxycarbonylamino-2-iodomethylcyclopropanecarboxylate

Guidance literature:: Multi-step reaction with 9 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: 87 percent / NaBH₄ / methanol / 0.33 h / 0 °C

8: 96 percent / Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

9: 89 percent / NaI / acetone / 3 h / 0 °C

With 1,3-dimethyl-2-phenyl-1,3,2-diazaphospholidine; hydrogenchloride; methanol; sodium tetrahydroborate; benzophenone; dimethylsulfide; ozone; triethylamine; sodium iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetone;
DOI:10.1016/0957-4166(96)00038-9