[1S-(1α,2α,3β)]-1-[N-(tert-butoxycarbonyl)-L-leucine methyl ester]-2-hydroxymethyl-3-phenylcyclopropane

Base Information

Chemical Name:[1S-(1α,2α,3β)]-1-[N-(tert-butoxycarbonyl)-L-leucine methyl ester]-2-hydroxymethyl-3-phenylcyclopropane
CAS No.:264921-59-7
Molecular Formula:C₂₂H₃₃NO₅
Molecular Weight:391.508
Hs Code.:

Synonyms:[1S-(1α,2α,3β)]-1-[N-(tert-butoxycarbonyl)-L-leucine methyl ester]-2-hydroxymethyl-3-phenylcyclopropane

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Chemical Property of [1S-(1α,2α,3β)]-1-[N-(tert-butoxycarbonyl)-L-leucine methyl ester]-2-hydroxymethyl-3-phenylcyclopropane

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Technology Process of [1S-(1α,2α,3β)]-1-[N-(tert-butoxycarbonyl)-L-leucine methyl ester]-2-hydroxymethyl-3-phenylcyclopropane

There total 1 articles about [1S-(1α,2α,3β)]-1-[N-(tert-butoxycarbonyl)-L-leucine methyl ester]-2-hydroxymethyl-3-phenylcyclopropane 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:

: 24424-99-5
di-tert-butyl dicarbonate

: (S)-2-(2-Hydroxymethyl-3-phenyl-cyclopropylamino)-4-methyl-pentanoic acid methyl ester

: [1R-(1α,2α,3β)]-1-[N-(tert-butoxycarbonyl)-L-leucine methyl ester]-2-hydroxymethyl-3-phenylcyclopropane

: 264921-59-7
[1S-(1α,2α,3β)]-1-[N-(tert-butoxycarbonyl)-L-leucine methyl ester]-2-hydroxymethyl-3-phenylcyclopropane

Guidance literature:: In acetonitrile; at 20 ℃; for 72h;
DOI:10.1021/jo991288h

Reference yield: 85.0%

: 264921-59-7
[1S-(1α,2α,3β)]-1-[N-(tert-butoxycarbonyl)-L-leucine methyl ester]-2-hydroxymethyl-3-phenylcyclopropane

: 264921-60-0
[1S-(1α,2α,3β)]-1-[N-(tert-butoxycarbonyl)-L-leucine methyl ester]-2-carboxy-3-phenylcyclopropane

Guidance literature:: With ruthenium trichloride; sodium periodate; sodium hydrogencarbonate; In chloroform; water; acetonitrile; at 20 ℃; for 0.5h;
DOI:10.1021/jo991288h

Reference yield:

: 264921-59-7
[1S-(1α,2α,3β)]-1-[N-(tert-butoxycarbonyl)-L-leucine methyl ester]-2-hydroxymethyl-3-phenylcyclopropane

: (S)-2-{(1R,2S,3R)-2-[((1R,2S)-2-{(R)-2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-1-hydroxy-ethyl}-cyclopropanecarbonyl)-amino]-3-phenyl-cyclopropylamino}-4-methyl-pentanoic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 85 percent / RuCl₃; NaIO₄; NaHCO₃ / acetonitrile; CHCl₃; H₂O / 0.5 h / 20 °C

2: Et₃N / acetone; H₂O / 1 h / 0 °C

3: NaN₃ / CH₂Cl₂; H₂O / 1 h / 0 °C

4: CH₂Cl₂; toluene

5: 82 mg / 12 h / Heating

6: 46 mg / Pd(PPh₃)4; Bu₃SnH / CH₂Cl₂ / 3 h / 20 °C

7: 85 percent / TMSI / acetonitrile / 1 h / 20 °C

With ruthenium trichloride; sodium periodate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium azide; trimethylsilyl iodide; tri-n-butyl-tin hydride; sodium hydrogencarbonate; triethylamine; In dichloromethane; chloroform; water; acetone; toluene; acetonitrile; 1: Oxidation / 2: Condensation / 3: Substitution / 4: Curtius rearrangement / 5: Addition / 6: Condensation / 7: Hydrolysis;
DOI:10.1021/jo991288h