Butanedioic acid, 2-[3-[[(4-nitrophenoxy)carbonyl]oxy]propyl]-3-[[4-(phenylmethoxy)phenyl] methyl]-, 1-(1,1-dimethylethyl) 4-(phenylmethyl) ester, (2S,3R)-

Base Information

Chemical Name:Butanedioic acid, 2-[3-[[(4-nitrophenoxy)carbonyl]oxy]propyl]-3-[[4-(phenylmethoxy)phenyl] methyl]-, 1-(1,1-dimethylethyl) 4-(phenylmethyl) ester, (2S,3R)-
CAS No.:377088-77-2
Molecular Formula:C39H41NO10
Molecular Weight:683.755
Hs Code.:
Mol file:377088-77-2.mol

Butanedioic acid,
2-[3-[[(4-nitrophenoxy)carbonyl]oxy]propyl]-3-[[4-(phenylmethoxy)phenyl]
methyl]-, 1-(1,1-dimethylethyl) 4-(phenylmethyl) ester, (2S,3R)-

Synonyms:

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Chemical Property of Butanedioic acid, 2-[3-[[(4-nitrophenoxy)carbonyl]oxy]propyl]-3-[[4-(phenylmethoxy)phenyl] methyl]-, 1-(1,1-dimethylethyl) 4-(phenylmethyl) ester, (2S,3R)-

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Technology Process of Butanedioic acid, 2-[3-[[(4-nitrophenoxy)carbonyl]oxy]propyl]-3-[[4-(phenylmethoxy)phenyl] methyl]-, 1-(1,1-dimethylethyl) 4-(phenylmethyl) ester, (2S,3R)-

There total 10 articles about Butanedioic acid, 2-[3-[[(4-nitrophenoxy)carbonyl]oxy]propyl]-3-[[4-(phenylmethoxy)phenyl] methyl]-, 1-(1,1-dimethylethyl) 4-(phenylmethyl) ester, (2S,3R)- 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: 78.0%

: 7693-46-1
4-Nitrophenyl chloroformate

: (2R,3S)-2-(4-Benzyloxy-benzyl)-3-(3-hydroxy-propyl)-succinic acid 1-benzyl ester 4-tert-butyl ester

: 377088-77-2
1-benzyl-4-tert-butyl(2R,3S)-2-[4-(benzyloxy)benzyl]-3-(3-{[(4-nitrophenoxy)carbonyl]oxy}propyl)butanedioate

Guidance literature:: With 4-methyl-morpholine; In dichloromethane; at 20 ℃; for 3h;
DOI:10.1021/jm0155502

Reference yield:

: 5597-50-2
3-(4-hydroxyphenyl)propionic acid methyl ester

: 377088-77-2
1-benzyl-4-tert-butyl(2R,3S)-2-[4-(benzyloxy)benzyl]-3-(3-{[(4-nitrophenoxy)carbonyl]oxy}propyl)butanedioate

Guidance literature:: Multi-step reaction with 9 steps

1.1: 76 percent / K₂CO₃ / dimethylformamide / 3 h / 80 °C

2.1: 98 percent / LiOH; H₂O / tetrahydrofuran / 2 h / 20 °C

3.1: pivaloyl chloride; DIEA / tetrahydrofuran / 1 h / -30 °C

3.2: 60 percent / LiCl / tetrahydrofuran / -30 - 20 °C

4.1: diisopropylamine; n-BuLi / tetrahydrofuran / 1 h / -78 °C

4.2: 61 percent / tetrahydrofuran / -78 - 0 °C

5.1: 100 percent / LiOH; H₂O₂ / tetrahydrofuran; H₂O / 3 h / 0 °C

6.1: LDA / tetrahydrofuran / 1 h / -78 °C

6.2: 84 percent / tetrahydrofuran / 0 - 5 °C

7.1: LDA; Et₂AlCl / tetrahydrofuran / -78 - 20 °C

7.2: 7.69 g / DBU / benzene / 50 °C

8.1: 9-BBN / tetrahydrofuran / 20 °C

8.2: 87 percent / NaOAc; H₂O₂ / tetrahydrofuran; H₂O / 0 °C

9.1: 78 percent / NMM / CH₂Cl₂ / 3 h / 20 °C

With 4-methyl-morpholine; lithium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; water; dihydrogen peroxide; diethylaluminium chloride; pivaloyl chloride; potassium carbonate; diisopropylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jm0155502

Reference yield:

: (2R,3R)-2-Allyl-3-(4-benzyloxy-benzyl)-succinic acid 1-tert-butyl ester

: 377088-77-2
1-benzyl-4-tert-butyl(2R,3S)-2-[4-(benzyloxy)benzyl]-3-(3-{[(4-nitrophenoxy)carbonyl]oxy}propyl)butanedioate

Guidance literature:: Multi-step reaction with 3 steps

1.1: LDA; Et₂AlCl / tetrahydrofuran / -78 - 20 °C

1.2: 7.69 g / DBU / benzene / 50 °C

2.1: 9-BBN / tetrahydrofuran / 20 °C

2.2: 87 percent / NaOAc; H₂O₂ / tetrahydrofuran; H₂O / 0 °C

3.1: 78 percent / NMM / CH₂Cl₂ / 3 h / 20 °C

With 4-methyl-morpholine; 9-borabicyclo[3.3.1]nonane dimer; diethylaluminium chloride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jm0155502