4-Nitro-benzoic acid (E)-(1S,2S,3R)-1-[(E)-(S)-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-3-methyl-pent-3-enyl]-3-methoxy-6-(4-methoxy-benzyloxy)-2,4-dimethyl-hex-4-enyl ester

Base Information

Chemical Name:4-Nitro-benzoic acid (E)-(1S,2S,3R)-1-[(E)-(S)-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-3-methyl-pent-3-enyl]-3-methoxy-6-(4-methoxy-benzyloxy)-2,4-dimethyl-hex-4-enyl ester
CAS No.:1027202-98-7
Molecular Formula:C₃₆H₅₃NO₉Si
Molecular Weight:671.904
Hs Code.:

4-Nitro-benzoic acid (E)-(1S,2S,3R)-1-[(E)-(S)-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-3-methyl-pent-3-enyl]-3-methoxy-6-(4-methoxy-benzyloxy)-2,4-dimethyl-hex-4-enyl ester

Synonyms:4-Nitro-benzoic acid (E)-(1S,2S,3R)-1-[(E)-(S)-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-3-methyl-pent-3-enyl]-3-methoxy-6-(4-methoxy-benzyloxy)-2,4-dimethyl-hex-4-enyl ester

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Chemical Property of 4-Nitro-benzoic acid (E)-(1S,2S,3R)-1-[(E)-(S)-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-3-methyl-pent-3-enyl]-3-methoxy-6-(4-methoxy-benzyloxy)-2,4-dimethyl-hex-4-enyl ester

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Technology Process of 4-Nitro-benzoic acid (E)-(1S,2S,3R)-1-[(E)-(S)-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-3-methyl-pent-3-enyl]-3-methoxy-6-(4-methoxy-benzyloxy)-2,4-dimethyl-hex-4-enyl ester

There total 7 articles about 4-Nitro-benzoic acid (E)-(1S,2S,3R)-1-[(E)-(S)-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-3-methyl-pent-3-enyl]-3-methoxy-6-(4-methoxy-benzyloxy)-2,4-dimethyl-hex-4-enyl 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: 86.0%

: 555-16-8
4-nitrobenzaldehdye

: (2E,9E)-(7S,8R)-1-(tert-Butyl-dimethyl-silanyloxy)-6-hydroxy-8-methoxy-11-(4-methoxy-benzyloxy)-3,7,9-trimethyl-undeca-2,9-dien-4-one

: 1027202-98-7
4-Nitro-benzoic acid (E)-(1S,2S,3R)-1-[(E)-(S)-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-3-methyl-pent-3-enyl]-3-methoxy-6-(4-methoxy-benzyloxy)-2,4-dimethyl-hex-4-enyl ester

Guidance literature:: With samarium diiodide; In tetrahydrofuran; at 0 ℃; for 1.5h;
DOI:10.1021/ol049701h

Reference yield:

: 147438-60-6
(E)-(2R,3R)-3-Methoxy-6-(4-methoxy-benzyloxy)-2,4-dimethyl-hex-4-enal

: 1027202-98-7
4-Nitro-benzoic acid (E)-(1S,2S,3R)-1-[(E)-(S)-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-3-methyl-pent-3-enyl]-3-methoxy-6-(4-methoxy-benzyloxy)-2,4-dimethyl-hex-4-enyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: (+)-chlorodiisopinocamphenyl borane; Et₃N / CH₂Cl₂ / 3 h / -78 °C

1.2: 65 percent / CH₂Cl₂ / 26 h / -78 - -15 °C

2.1: 86 percent / SmI₂ / tetrahydrofuran / 1.5 h / 0 °C

With samarium diiodide; triethylamine; B-chlorodiisopinocampheylborane; In tetrahydrofuran; dichloromethane; 2.1: Evans-Tishchenko reaction;
DOI:10.1021/ol049701h

Reference yield:

: 197227-70-6
(2E)-4-[(4-methoxybenzyl)oxy]-2-methylbut-2-enal

: 1027202-98-7
4-Nitro-benzoic acid (E)-(1S,2S,3R)-1-[(E)-(S)-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-3-methyl-pent-3-enyl]-3-methoxy-6-(4-methoxy-benzyloxy)-2,4-dimethyl-hex-4-enyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: dibutylboron triflate; Et₃N / CH₂Cl₂ / 0.42 h / 0 °C

1.2: 85 percent / CH₂Cl₂ / -78 - 20 °C

2.1: trimethylaluminum / tetrahydrofuran; toluene / 0.83 h / 20 °C

2.2: tetrahydrofuran; toluene / 2.5 h / 0 - 20 °C

3.1: 3.4 g / NaH / tetrahydrofuran; dimethylformamide / 1 h / 0 °C

4.1: 98 percent / DIBAL-H / tetrahydrofuran; hexane / 1 h / -78 °C

5.1: (+)-chlorodiisopinocamphenyl borane; Et₃N / CH₂Cl₂ / 3 h / -78 °C

5.2: 65 percent / CH₂Cl₂ / 26 h / -78 - -15 °C

6.1: 86 percent / SmI₂ / tetrahydrofuran / 1.5 h / 0 °C

With samarium diiodide; di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; sodium hydride; diisobutylaluminium hydride; triethylamine; B-chlorodiisopinocampheylborane; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Evans aldol reaction / 1.2: Evans aldol reaction / 6.1: Evans-Tishchenko reaction;
DOI:10.1021/ol049701h