C₂₈H₃₈O₆

Base Information

• Chemical Name: C₂₈H₃₈O₆
• CAS No.: 814920-13-3
• Molecular Formula: C₂₈H₃₈O₆
• Molecular Weight: 470.606

Synonyms:C₂₈H₃₈O₆

Chemical Property of C₂₈H₃₈O₆

Chemical Property:

Purity/Quality:

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Technology Process of C₂₈H₃₈O₆

There total 26 articles about C₂₈H₃₈O₆ 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: 92.0%

C27H36O7 (814920-12-2) + Methyltriphenylphosphonium bromide (1779-49-3) → C28H38O6 (814920-13-3)

Guidance literature:

Methyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; hexane; at 20 ℃; for 0.416667h;

C₂₇H₃₆O₇; In tetrahydrofuran; hexane; at 0 - 20 ℃;

DOI:10.1021/jo048681u

Reference yield:

(1S,3R,7R,8S,9R,10S,11S)-9-Benzyloxymethyl-10-hydroxymethyl-11-methyl-7-trimethylsilanyloxy-4-oxa-tricyclo[5.3.1.03,8]undecan-5-one (312923-90-3) → C28H38O6 (814920-13-3)

Guidance literature:

Multi-step reaction with 25 steps

1.1: 29 percent / diacetoxyiodobenzene; iodine / CH₂Cl₂ / 0.83 h / 0 °C / Irradiation

2.1: 86 percent / i-Pr₂NEt / CH₂Cl₂ / 10 h / 20 °C

3.1: O₃ / CH₂Cl₂ / 0.25 h / -78 °C

3.2: 83 percent / PPh₃ / CH₂Cl₂ / -78 - 20 °C

4.1: Zn(BH₄)2 / diethyl ether / 0.5 h / 0 °C

5.1: tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C

6.1: 2.25 g / PPTS / acetone / 14 h / 20 °C

7.1: LiHMDS; HMPA / tetrahydrofuran / 1.5 h / -78 °C

7.2: 86 percent / tetrahydrofuran / 0.92 h / -78 - -40 °C

8.1: O₃ / CH₂Cl₂ / 0.08 h / -78 °C

8.2: triphenylphosphine / CH₂Cl₂ / -78 - 20 °C

9.1: 197 mg / NaBH₄ / CH₂Cl₂; methanol / 0.08 h / 20 °C

10.1: 97 percent / n-Bu₃P / tetrahydrofuran / 1.67 h / -78 - 20 °C

11.1: 252 mg / H₂O₂ / tetrahydrofuran / 12 h / 20 °C

12.1: 335 mg / LiAlH₄ / dioxane / 0.02 h / Heating

13.1: 345 mg / Et₃N; DMAP / CH₂Cl₂ / 1.17 h / 20 °C

14.1: 93 percent / 4-methylmorpholine N-oxide / TPAP / acetonitrile / 1 h / 20 °C

15.1: O₃ / CH₂Cl₂ / 0.67 h / -78 °C

15.2: 88 percent / triphenylphosphine / CH₂Cl₂ / -78 - 20 °C

16.1: 86 percent / SmI₂; HMPA / tetrahydrofuran / 0.75 h / -40 - 0 °C

17.1: 87 percent / DMAP / tetrahydrofuran / 6 h / 20 °C

18.1: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.67 h / 20 °C

19.1: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.58 h / 20 °C

20.1: 90 percent / NaBH₄; CeCl₃*7H₂O / methanol / 0.25 h / 0 °C

21.1: 77 percent / zinc chloride / CH₂Cl₂ / 0.75 h

22.1: 45 percent / (TMS)3SiH; AIBN / benzene / 0.33 h / Heating

23.1: 91 percent / cesium fluoride / dimethylformamide / 46 h / 130 °C

24.1: 91 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.92 h / 20 °C

25.1: n-BuLi / tetrahydrofuran; hexane / 0.42 h / 20 °C

25.2: 92 percent / tetrahydrofuran; hexane / 0 - 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; samarium diiodide; cerium(III) chloride; zinc(II) tetrahydroborate; 2,2'-azobis(isobutyronitrile); tributylphosphine; [bis(acetoxy)iodo]benzene; tris-(trimethylsilyl)silane; tetrabutyl ammonium fluoride; dihydrogen peroxide; iodine; pyridinium p-toluenesulfonate; Dess-Martin periodane; ozone; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; cesium fluoride; zinc(II) chloride; lithium hexamethyldisilazane; tetrapropylammonium perruthennate; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile; benzene; 11.1: Grieco olefination / 19.1: Dess-Martin oxidation / 24.1: Dess-Martin oxidation / 25.2: Wittig reaction;

DOI:10.1021/jo048681u

Reference yield:

(1S,3R,7S,8S,9R,10R,11R)-9-Benzyloxymethyl-7,11-dihydroxy-10-(2-trimethylsilanyl-ethoxymethoxymethyl)-4-oxa-tricyclo[5.3.1.03,8]undecan-5-one → C28H38O6 (814920-13-3)

Guidance literature:

Multi-step reaction with 20 steps

1.1: 2.25 g / PPTS / acetone / 14 h / 20 °C

2.1: LiHMDS; HMPA / tetrahydrofuran / 1.5 h / -78 °C

2.2: 86 percent / tetrahydrofuran / 0.92 h / -78 - -40 °C

3.1: O₃ / CH₂Cl₂ / 0.08 h / -78 °C

3.2: triphenylphosphine / CH₂Cl₂ / -78 - 20 °C

4.1: 197 mg / NaBH₄ / CH₂Cl₂; methanol / 0.08 h / 20 °C

5.1: 97 percent / n-Bu₃P / tetrahydrofuran / 1.67 h / -78 - 20 °C

6.1: 252 mg / H₂O₂ / tetrahydrofuran / 12 h / 20 °C

7.1: 335 mg / LiAlH₄ / dioxane / 0.02 h / Heating

8.1: 345 mg / Et₃N; DMAP / CH₂Cl₂ / 1.17 h / 20 °C

9.1: 93 percent / 4-methylmorpholine N-oxide / TPAP / acetonitrile / 1 h / 20 °C

10.1: O₃ / CH₂Cl₂ / 0.67 h / -78 °C

10.2: 88 percent / triphenylphosphine / CH₂Cl₂ / -78 - 20 °C

11.1: 86 percent / SmI₂; HMPA / tetrahydrofuran / 0.75 h / -40 - 0 °C

12.1: 87 percent / DMAP / tetrahydrofuran / 6 h / 20 °C

13.1: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.67 h / 20 °C

14.1: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.58 h / 20 °C

15.1: 90 percent / NaBH₄; CeCl₃*7H₂O / methanol / 0.25 h / 0 °C

16.1: 77 percent / zinc chloride / CH₂Cl₂ / 0.75 h

17.1: 45 percent / (TMS)3SiH; AIBN / benzene / 0.33 h / Heating

18.1: 91 percent / cesium fluoride / dimethylformamide / 46 h / 130 °C

19.1: 91 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.92 h / 20 °C

20.1: n-BuLi / tetrahydrofuran; hexane / 0.42 h / 20 °C

20.2: 92 percent / tetrahydrofuran; hexane / 0 - 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; samarium diiodide; cerium(III) chloride; 2,2'-azobis(isobutyronitrile); tributylphosphine; tris-(trimethylsilyl)silane; tetrabutyl ammonium fluoride; dihydrogen peroxide; pyridinium p-toluenesulfonate; Dess-Martin periodane; ozone; 4-methylmorpholine N-oxide; triethylamine; cesium fluoride; zinc(II) chloride; lithium hexamethyldisilazane; tetrapropylammonium perruthennate; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile; benzene; 6.1: Grieco olefination / 14.1: Dess-Martin oxidation / 19.1: Dess-Martin oxidation / 20.2: Wittig reaction;

DOI:10.1021/jo048681u

upstream raw materials:

C₂₇H₃₆O₇

Methyltriphenylphosphonium bromide

C₂₇H₃₈O₇

C₂₈H₄₂O₇Si

Downstream raw materials:

C₄₈H₇₇IO₈Si₂

C₄₈H₇₇IO₈Si₂

C₄₈H₇₅IO₈Si₂

C₄₈H₇₆O₈Si₂

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