3-(3-benzyloxy-2-iodo-4-methoxy-5-methyl-phenyl)-2-tert-butoxycarbonylamino-propionic acid

Base Information

Chemical Name:3-(3-benzyloxy-2-iodo-4-methoxy-5-methyl-phenyl)-2-tert-butoxycarbonylamino-propionic acid
CAS No.:442663-28-7
Molecular Formula:C₂₃H₂₈INO₆
Molecular Weight:541.383
Hs Code.:

3-(3-benzyloxy-2-iodo-4-methoxy-5-methyl-phenyl)-2-<i>tert</i>-butoxycarbonylamino-propionic acid

Synonyms:3-(3-benzyloxy-2-iodo-4-methoxy-5-methyl-phenyl)-2-tert-butoxycarbonylamino-propionic acid

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Chemical Property of 3-(3-benzyloxy-2-iodo-4-methoxy-5-methyl-phenyl)-2-tert-butoxycarbonylamino-propionic acid

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Technology Process of 3-(3-benzyloxy-2-iodo-4-methoxy-5-methyl-phenyl)-2-tert-butoxycarbonylamino-propionic acid

There total 14 articles about 3-(3-benzyloxy-2-iodo-4-methoxy-5-methyl-phenyl)-2-tert-butoxycarbonylamino-propionic acid 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%

: 442663-27-6
3-(3-benzyloxy-2-iodo-4-methoxy-5-methyl-phenyl)-2-tert-butoxycarbonylamino-propionic acid methyl ester

: 442663-28-7
3-(3-benzyloxy-2-iodo-4-methoxy-5-methyl-phenyl)-2-tert-butoxycarbonylamino-propionic acid

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; methanol; water; at 0 - 20 ℃;
DOI:10.1021/ja026216d

Reference yield:

: 100-39-0
benzyl bromide

: 442663-28-7
3-(3-benzyloxy-2-iodo-4-methoxy-5-methyl-phenyl)-2-tert-butoxycarbonylamino-propionic acid

Guidance literature:: Multi-step reaction with 4 steps

1: 98 percent / K₂CO₃ / acetonitrile / 0.67 h / Heating

2: 93 percent / N,N,N',N'-tetramethylguanidine / CH₂Cl₂ / 24 h / 20 °C

3: H₂; Rh[(COD)-(S,S)-Et-DuPHOS]⁺OTf^- / ethyl acetate / 22 h / 50 °C / 25858.1 Torr

4: 100 percent / lithium hydroxide / methanol; tetrahydrofuran; H₂O / 0 - 20 °C

With lithium hydroxide; (+)-1,2-bis((2S,,5S)-2,5-diethylphospholano)benzene(cyclooctadiene)rhodium(I) trifluoromethanesulfonate; hydrogen; potassium carbonate; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; acetonitrile; 2: Horner-Emmons reaction;
DOI:10.1021/ja026216d

Reference yield:

: 488-17-5
3-methylbenzene-1,2-diol

: 442663-28-7
3-(3-benzyloxy-2-iodo-4-methoxy-5-methyl-phenyl)-2-tert-butoxycarbonylamino-propionic acid

Guidance literature:: Multi-step reaction with 13 steps

1.1: 83 percent / TEA / CH₂Cl₂ / 0 °C

2.1: 97 percent / Br₂; AcOH / CH₂Cl₂ / 0.5 h / 20 °C

3.1: 96 percent / K₂CO₃ / acetone / 1 h / Heating

4.1: 97 percent / aq. NaOH / ethanol / 0.5 h / Heating

5.1: 97 percent / i-Pr₂NEt / CH₂Cl₂ / 0 - 20 °C

6.1: 79 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 60 °C

7.1: CSA / methanol / 1 h / 20 °C

8.1: n-BuLi / diethyl ether; hexane / 0 - 20 °C

8.2: I₂ / diethyl ether; hexane / 0 °C

9.1: 314 mg / conc. HCl / tetrahydrofuran / 0.25 h / 20 °C

10.1: 98 percent / K₂CO₃ / acetonitrile / 0.67 h / Heating

11.1: 93 percent / N,N,N',N'-tetramethylguanidine / CH₂Cl₂ / 24 h / 20 °C

12.1: H₂; Rh[(COD)-(S,S)-Et-DuPHOS]⁺OTf^- / ethyl acetate / 22 h / 50 °C / 25858.1 Torr

13.1: 100 percent / lithium hydroxide / methanol; tetrahydrofuran; H₂O / 0 - 20 °C

With hydrogenchloride; lithium hydroxide; sodium hydroxide; n-butyllithium; (+)-1,2-bis((2S,,5S)-2,5-diethylphospholano)benzene(cyclooctadiene)rhodium(I) trifluoromethanesulfonate; TEA; camphor-10-sulfonic acid; hydrogen; bromine; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; ethyl acetate; acetone; acetonitrile; 11.1: Horner-Emmons reaction;
DOI:10.1021/ja026216d