(2Z)-2-(((2S,4R,5S)-5-(benzamido)-2-phenyl-[1,3]dioxan-4-yl)methylene)-octanoic acid tert-butyl ester

Base Information

Chemical Name:(2Z)-2-(((2S,4R,5S)-5-(benzamido)-2-phenyl-[1,3]dioxan-4-yl)methylene)-octanoic acid tert-butyl ester
CAS No.:881177-92-0
Molecular Formula:C₃₀H₃₉NO₅
Molecular Weight:493.643
Hs Code.:

Synonyms:(2Z)-2-(((2S,4R,5S)-5-(benzamido)-2-phenyl-[1,3]dioxan-4-yl)methylene)-octanoic acid tert-butyl ester

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Chemical Property of (2Z)-2-(((2S,4R,5S)-5-(benzamido)-2-phenyl-[1,3]dioxan-4-yl)methylene)-octanoic acid tert-butyl ester

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Technology Process of (2Z)-2-(((2S,4R,5S)-5-(benzamido)-2-phenyl-[1,3]dioxan-4-yl)methylene)-octanoic acid tert-butyl ester

There total 6 articles about (2Z)-2-(((2S,4R,5S)-5-(benzamido)-2-phenyl-[1,3]dioxan-4-yl)methylene)-octanoic 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: 93.0%

: 98-88-4
benzoyl chloride

: 881177-88-4
(2Z)-2-(((2S,4R,5S)-5-amino-2-phenyl-[1,3]dioxan-4-yl)methylene)-octanoic acid tert-butyl ester

: 881177-92-0
(2Z)-2-(((2S,4R,5S)-5-(benzamido)-2-phenyl-[1,3]dioxan-4-yl)methylene)-octanoic acid tert-butyl ester

Guidance literature:: With triethylamine; In tetrahydrofuran; for 24h;
DOI:10.1002/anie.200501983

Reference yield:

: C₆H₁₃CHCO₂C₄H₉P(OC₆H₅)2

: 881177-92-0
(2Z)-2-(((2S,4R,5S)-5-(benzamido)-2-phenyl-[1,3]dioxan-4-yl)methylene)-octanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: LiCl; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0.5 h / -78 °C

1.2: 67 percent / tetrahydrofuran / 18 h / -78 °C

2.1: pyridine / CH₂Cl₂ / -40 °C

3.1: 0.478 g / NaN₃ / CH₂Cl₂; dimethylformamide / 20 h / 20 °C

4.1: Ph₃P / tetrahydrofuran

4.2: 94 percent / H₂O / tetrahydrofuran / 74 h / 60 °C

5.1: 93 percent / Et₃N / tetrahydrofuran / 24 h

With pyridine; sodium azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; lithium chloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/anie.200501983

Reference yield:

: 881177-86-2
(2Z)-2-(((2S,4R,5R)-5-hydroxy-2-phenyl-[1,3]dioxan-4-yl)methylene)-octanoic acid tert-butyl ester

: 881177-92-0
(2Z)-2-(((2S,4R,5S)-5-(benzamido)-2-phenyl-[1,3]dioxan-4-yl)methylene)-octanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: pyridine / CH₂Cl₂ / -40 °C

2.1: 0.478 g / NaN₃ / CH₂Cl₂; dimethylformamide / 20 h / 20 °C

3.1: Ph₃P / tetrahydrofuran

3.2: 94 percent / H₂O / tetrahydrofuran / 74 h / 60 °C

4.1: 93 percent / Et₃N / tetrahydrofuran / 24 h

With pyridine; sodium azide; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/anie.200501983