(2S,3R)-3-(N-methoxycarbonyl-N-benzyl)amino-1,2-O-isopropylidene-4-pentene-1,2-diol

Base Information

Chemical Name:(2S,3R)-3-(N-methoxycarbonyl-N-benzyl)amino-1,2-O-isopropylidene-4-pentene-1,2-diol
CAS No.:360074-03-9
Molecular Formula:C₁₇H₂₃NO₄
Molecular Weight:305.374
Hs Code.:

Synonyms:(2S,3R)-3-(N-methoxycarbonyl-N-benzyl)amino-1,2-O-isopropylidene-4-pentene-1,2-diol

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Chemical Property of (2S,3R)-3-(N-methoxycarbonyl-N-benzyl)amino-1,2-O-isopropylidene-4-pentene-1,2-diol

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Technology Process of (2S,3R)-3-(N-methoxycarbonyl-N-benzyl)amino-1,2-O-isopropylidene-4-pentene-1,2-diol

There total 7 articles about (2S,3R)-3-(N-methoxycarbonyl-N-benzyl)amino-1,2-O-isopropylidene-4-pentene-1,2-diol 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%

: 79-22-1
methyl chloroformate

: 181303-63-9
(R)-N-benzyl-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-2-en-1-amine

: 360074-03-9
(2S,3R)-3-(N-methoxycarbonyl-N-benzyl)amino-1,2-O-isopropylidene-4-pentene-1,2-diol

Guidance literature:: With triethylamine; In tetrahydrofuran; at 0 - 20 ℃; for 2.5h;
DOI:10.1021/ja011128z

Reference yield:

: 360074-00-6
C₁₉H₂₅NO₅

: 360074-03-9
(2S,3R)-3-(N-methoxycarbonyl-N-benzyl)amino-1,2-O-isopropylidene-4-pentene-1,2-diol

Guidance literature:: Multi-step reaction with 4 steps

1: 67 percent / triethylsilane; palladium(II) acetate; triethylamine / CH₂Cl₂ / 2 h / 20 °C

2: n-BuLi / toluene; hexane / 1 h / 0 °C

3: 38 percent / zinc; copper(II) acetate / acetic acid; H₂O / 1.5 h / 70 °C

4: 89 percent / Et₃N / tetrahydrofuran / 2.5 h / 0 - 20 °C

With triethylsilane; n-butyllithium; copper diacetate; palladium diacetate; triethylamine; zinc; In tetrahydrofuran; hexane; dichloromethane; water; acetic acid; toluene; 2: <2,3>-Wittig rearrangement;
DOI:10.1021/ja011128z

Reference yield:

: 79060-23-4
(2E)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-ol

: 360074-03-9
(2S,3R)-3-(N-methoxycarbonyl-N-benzyl)amino-1,2-O-isopropylidene-4-pentene-1,2-diol

Guidance literature:: Multi-step reaction with 5 steps

1: 92 percent / 1,1-(azodicarbonyl)dipiperidine; tributylphosphine / benzene / 0.33 h / 20 °C

2: 67 percent / triethylsilane; palladium(II) acetate; triethylamine / CH₂Cl₂ / 2 h / 20 °C

3: n-BuLi / toluene; hexane / 1 h / 0 °C

4: 38 percent / zinc; copper(II) acetate / acetic acid; H₂O / 1.5 h / 70 °C

5: 89 percent / Et₃N / tetrahydrofuran / 2.5 h / 0 - 20 °C

With triethylsilane; n-butyllithium; tributylphosphine; copper diacetate; palladium diacetate; triethylamine; zinc; 1,1'-azodicarbonyl-dipiperidine; In tetrahydrofuran; hexane; dichloromethane; water; acetic acid; toluene; benzene; 1: Mitsunobu reaction / 3: <2,3>-Wittig rearrangement;
DOI:10.1021/ja011128z