(+)-3,5-dinitrobenzoic acid (2R,4S,5S,6S,7S)-7-methoxymethoxymethyl-4,7-dimethyl-6-(2-oxoethyl)-1-oxaspiro[4.4]non-2-ylmethyl ester

Base Information

Chemical Name:(+)-3,5-dinitrobenzoic acid (2R,4S,5S,6S,7S)-7-methoxymethoxymethyl-4,7-dimethyl-6-(2-oxoethyl)-1-oxaspiro[4.4]non-2-ylmethyl ester
CAS No.:890028-28-1
Molecular Formula:C₂₃H₃₀N₂O₁₀
Molecular Weight:494.499
Hs Code.:

Synonyms:(+)-3,5-dinitrobenzoic acid (2R,4S,5S,6S,7S)-7-methoxymethoxymethyl-4,7-dimethyl-6-(2-oxoethyl)-1-oxaspiro[4.4]non-2-ylmethyl ester

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Chemical Property of (+)-3,5-dinitrobenzoic acid (2R,4S,5S,6S,7S)-7-methoxymethoxymethyl-4,7-dimethyl-6-(2-oxoethyl)-1-oxaspiro[4.4]non-2-ylmethyl ester

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Technology Process of (+)-3,5-dinitrobenzoic acid (2R,4S,5S,6S,7S)-7-methoxymethoxymethyl-4,7-dimethyl-6-(2-oxoethyl)-1-oxaspiro[4.4]non-2-ylmethyl ester

There total 28 articles about (+)-3,5-dinitrobenzoic acid (2R,4S,5S,6S,7S)-7-methoxymethoxymethyl-4,7-dimethyl-6-(2-oxoethyl)-1-oxaspiro[4.4]non-2-ylmethyl 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: 95.0%

: 890028-14-5
(+)-3,5-dinitrobenzoic acid (2R,4S,5S,6S,7S)-6-(2-hydroxyethyl)-7-methoxymethoxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-2-ylmethyl ester

: 890028-28-1
(+)-3,5-dinitrobenzoic acid (2R,4S,5S,6S,7S)-7-methoxymethoxymethyl-4,7-dimethyl-6-(2-oxoethyl)-1-oxaspiro[4.4]non-2-ylmethyl ester

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 20 ℃;
DOI:10.1021/ol060437x

Reference yield:

: 890027-50-6
(R)-acetic acid 4-hydroxy-2-methoxymethoxymethyl-2-methylbutyl ester

: 890028-28-1
(+)-3,5-dinitrobenzoic acid (2R,4S,5S,6S,7S)-7-methoxymethoxymethyl-4,7-dimethyl-6-(2-oxoethyl)-1-oxaspiro[4.4]non-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 17 steps

1.1: 96 percent / PPTS / CH₂Cl₂ / 20 °C

2.1: 99 percent / K₂CO₃ / methanol / 20 °C

3.1: 87 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

4.1: t-BuOK / tetrahydrofuran / 0.17 h / 0 °C

4.2: 100 percent / tetrahydrofuran / -78 - 20 °C

5.1: 100 percent / DIBAL-H / CH₂Cl₂ / -78 °C

6.1: 96 percent / 2,6-lutidine; MsCl; LiCl / dimethylformamide / 0 °C

7.1: 86 percent / HMPA; MeLi / diethyl ether / -65 °C

8.1: 100 percent / PPTs / ethanol / 20 °C

9.1: 92 percent / imidazole; I₂ / benzene / 20 °C

10.1: t-BuLi / diethyl ether; pentane / 0.25 h / -78 °C

10.2: 84 percent / diethyl ether; pentane

11.1: 40 percent / TiCl₃(Oi-Pr) / CH₂Cl₂ / 4 h / -78 °C

12.1: 9-BBN / tetrahydrofuran / 0 - 20 °C

12.2: 100 percent / NaOH; H₂O₂ / tetrahydrofuran / 20 °C

13.1: 93 percent / PPTS / CH₂Cl₂ / 20 °C

14.1: 97 percent / TBAF / tetrahydrofuran / 20 °C

15.1: 100 percent / triethylamine; DMAP / CH₂Cl₂ / 20 °C

16.1: 74 percent / PPTS / ethanol / 20 °C

17.1: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; titanium(IV) trichloride isopropoxide; potassium tert-butylate; tetrabutyl ammonium fluoride; methyllithium; iodine; tert.-butyl lithium; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; lithium chloride; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; pentane; benzene; 3.1: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/ol060437x

Reference yield:

: 890027-44-8
(E)-(R)-2-hydroxymethyl-2-methyl-5-phenylpent-4-enoic acid methyl ester

: 890028-28-1
(+)-3,5-dinitrobenzoic acid (2R,4S,5S,6S,7S)-7-methoxymethoxymethyl-4,7-dimethyl-6-(2-oxoethyl)-1-oxaspiro[4.4]non-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 21 steps

1.1: 99 percent / NaI; DIPEA / CH₂Cl₂ / Heating

2.1: LiAlH₄ / diethyl ether / 20 °C

3.1: 19.24 g / pyridine; DMAP / CH₂Cl₂ / 20 °C

4.1: O₃ / methanol / -78 °C

4.2: 94 percent / NaBH₄ / methanol / -78 - 0 °C

5.1: 96 percent / PPTS / CH₂Cl₂ / 20 °C

6.1: 99 percent / K₂CO₃ / methanol / 20 °C

7.1: 87 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

8.1: t-BuOK / tetrahydrofuran / 0.17 h / 0 °C

8.2: 100 percent / tetrahydrofuran / -78 - 20 °C

9.1: 100 percent / DIBAL-H / CH₂Cl₂ / -78 °C

10.1: 96 percent / 2,6-lutidine; MsCl; LiCl / dimethylformamide / 0 °C

11.1: 86 percent / HMPA; MeLi / diethyl ether / -65 °C

12.1: 100 percent / PPTs / ethanol / 20 °C

13.1: 92 percent / imidazole; I₂ / benzene / 20 °C

14.1: t-BuLi / diethyl ether; pentane / 0.25 h / -78 °C

14.2: 84 percent / diethyl ether; pentane

15.1: 40 percent / TiCl₃(Oi-Pr) / CH₂Cl₂ / 4 h / -78 °C

16.1: 9-BBN / tetrahydrofuran / 0 - 20 °C

16.2: 100 percent / NaOH; H₂O₂ / tetrahydrofuran / 20 °C

17.1: 93 percent / PPTS / CH₂Cl₂ / 20 °C

18.1: 97 percent / TBAF / tetrahydrofuran / 20 °C

19.1: 100 percent / triethylamine; DMAP / CH₂Cl₂ / 20 °C

20.1: 74 percent / PPTS / ethanol / 20 °C

21.1: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; titanium(IV) trichloride isopropoxide; potassium tert-butylate; tetrabutyl ammonium fluoride; methyllithium; iodine; tert.-butyl lithium; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; ozone; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; lithium chloride; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; pentane; benzene; 7.1: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/ol060437x