(2R,4R,5R)-5-Benzyloxycarbonylamino-6-cyclohexyl-3,3-difluoro-4-iodo-2-isobutyl-hexanoic acid ethyl ester

Base Information

• Chemical Name: (2R,4R,5R)-5-Benzyloxycarbonylamino-6-cyclohexyl-3,3-difluoro-4-iodo-2-isobutyl-hexanoic acid ethyl ester
• CAS No.: 121584-80-3
• Molecular Formula: C₂₆H₃₈F₂INO₄
• Molecular Weight: 593.493

Synonyms:(2R,4R,5R)-5-Benzyloxycarbonylamino-6-cyclohexyl-3,3-difluoro-4-iodo-2-isobutyl-hexanoic acid ethyl ester

Chemical Property of (2R,4R,5R)-5-Benzyloxycarbonylamino-6-cyclohexyl-3,3-difluoro-4-iodo-2-isobutyl-hexanoic acid ethyl ester

Chemical Property:

Purity/Quality:

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Technology Process of (2R,4R,5R)-5-Benzyloxycarbonylamino-6-cyclohexyl-3,3-difluoro-4-iodo-2-isobutyl-hexanoic acid ethyl ester

There total 2 articles about (2R,4R,5R)-5-Benzyloxycarbonylamino-6-cyclohexyl-3,3-difluoro-4-iodo-2-isobutyl-hexanoic acid ethyl ester 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: 87.0%

(2R,4R,5R)-5-Amino-6-cyclohexyl-3,3-difluoro-4-iodo-2-isobutyl-hexanoic acid ethyl ester; hydrochloride (128777-40-2) + benzyl chloroformate (501-53-1,94274-21-2) → (2R,4R,5R)-5-Benzyloxycarbonylamino-6-cyclohexyl-3,3-difluoro-4-iodo-2-isobutyl-hexanoic acid ethyl ester (121584-80-3)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; at 0 ℃;

DOI:10.1021/ja00173a066

Reference yield:

(2R,3R,5R)-2-Cyclohexylmethyl-6-ethoxy-4,4-difluoro-3-iodo-5-isobutyl-2,3,4,5-tetrahydro-pyridine (121596-23-4,128707-37-9) → (2R,4R,5R)-5-Benzyloxycarbonylamino-6-cyclohexyl-3,3-difluoro-4-iodo-2-isobutyl-hexanoic acid ethyl ester (121584-80-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / HCl / tetrahydrofuran; H₂O / 0 °C

2: 87 percent / aq. NaHCO₃ / tetrahydrofuran / 0 °C

With hydrogenchloride; sodium hydrogencarbonate; In tetrahydrofuran; water;

DOI:10.1021/ja00173a066

Reference yield: 73.0%

(2R,4R,5R)-5-Benzyloxycarbonylamino-6-cyclohexyl-3,3-difluoro-4-iodo-2-isobutyl-hexanoic acid ethyl ester (121584-80-3) → (2R,4S,5R)-5-Benzyloxycarbonylamino-6-cyclohexyl-3,3-difluoro-4-hydroxy-2-isobutyl-hexanoic acid ethyl ester (121584-81-4,128707-38-0)

Guidance literature:

With buffered peroxytrifluoroacetic acid; In dichloromethane; at 0 ℃;

DOI:10.1021/ja00173a066

upstream raw materials:

(2R,4R,5R)-5-Amino-6-cyclohexyl-3,3-difluoro-4-iodo-2-isobutyl-hexanoic acid ethyl ester; hydrochloride

benzyl chloroformate

(2R,3R,5R)-2-Cyclohexylmethyl-6-ethoxy-4,4-difluoro-3-iodo-5-isobutyl-2,3,4,5-tetrahydro-pyridine

Downstream raw materials:

(2R,4S,5R)-5-Benzyloxycarbonylamino-6-cyclohexyl-3,3-difluoro-4-hydroxy-2-isobutyl-hexanoic acid ethyl ester

(2S,5S)-5-Benzyloxycarbonylamino-6-cyclohexyl-3,3-difluoro-2-isobutyl-4-oxo-hexanoic acid ethyl ester

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