(R)-2-Benzyloxycarbonylamino-6-bromo-5-hydroxy-hexanoic acid tert-butyl ester

Base Information

Chemical Name:(R)-2-Benzyloxycarbonylamino-6-bromo-5-hydroxy-hexanoic acid tert-butyl ester
CAS No.:183882-56-6
Molecular Formula:C₁₈H₂₆BrNO₅
Molecular Weight:416.312
Hs Code.:

Synonyms:(R)-2-Benzyloxycarbonylamino-6-bromo-5-hydroxy-hexanoic acid tert-butyl ester

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Chemical Property of (R)-2-Benzyloxycarbonylamino-6-bromo-5-hydroxy-hexanoic acid tert-butyl ester

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Technology Process of (R)-2-Benzyloxycarbonylamino-6-bromo-5-hydroxy-hexanoic acid tert-butyl ester

There total 8 articles about (R)-2-Benzyloxycarbonylamino-6-bromo-5-hydroxy-hexanoic acid tert-butyl 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: 99.0%

: 183882-55-5
(R)-2-Benzyloxycarbonylamino-4-oxiranyl-butyric acid tert-butyl ester

: 183882-56-6
(R)-2-Benzyloxycarbonylamino-6-bromo-5-hydroxy-hexanoic acid tert-butyl ester

Guidance literature:: With acetic acid; lithium bromide; In tetrahydrofuran; for 12h; Ambient temperature;
DOI:10.1016/0957-4166(96)00332-1

Reference yield:

: 5292-43-3
bromoacetic acid tert-butyl ester

: 183882-56-6
(R)-2-Benzyloxycarbonylamino-6-bromo-5-hydroxy-hexanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 70 percent / NH₃ / diethyl ether / -40 °C

2: 75 percent / BF₃*Et₂O / toluene / 2.5 h / Heating

3: 1.) LHMDS / 1.) THF, ether, -100 deg C, 20 min, 2.) THF, ether, from -100 to -30 deg C, 24 h

4: 89 percent / aq. citric acid / tetrahydrofuran / 84 h / Ambient temperature

5: 90 percent / Et₃N / dioxane; H₂O / 2.5 h / 0 °C

6: 97 percent / MCPBA / CH₂Cl₂ / 19 h / Ambient temperature

7: 99 percent / LiBr, AcOH / tetrahydrofuran / 12 h / Ambient temperature

With boron trifluoride diethyl etherate; ammonia; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; citric acid; lithium bromide; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; toluene;
DOI:10.1016/0957-4166(96)00332-1

Reference yield:

: 6456-74-2
Glycine tert-butyl ester

: 183882-56-6
(R)-2-Benzyloxycarbonylamino-6-bromo-5-hydroxy-hexanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 75 percent / BF₃*Et₂O / toluene / 2.5 h / Heating

2: 1.) LHMDS / 1.) THF, ether, -100 deg C, 20 min, 2.) THF, ether, from -100 to -30 deg C, 24 h

3: 89 percent / aq. citric acid / tetrahydrofuran / 84 h / Ambient temperature

4: 90 percent / Et₃N / dioxane; H₂O / 2.5 h / 0 °C

5: 97 percent / MCPBA / CH₂Cl₂ / 19 h / Ambient temperature

6: 99 percent / LiBr, AcOH / tetrahydrofuran / 12 h / Ambient temperature

With boron trifluoride diethyl etherate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; citric acid; lithium bromide; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; toluene;
DOI:10.1016/0957-4166(96)00332-1