(2S,3S)-2,3-epoxy-5,5-dimethyl-6-(2-tetrahydropyranyloxy)-1-trityloxyhexane

Base Information

Chemical Name:(2S,3S)-2,3-epoxy-5,5-dimethyl-6-(2-tetrahydropyranyloxy)-1-trityloxyhexane
CAS No.:155433-50-4
Molecular Formula:C₃₂H₃₈O₄
Molecular Weight:486.651
Hs Code.:

Synonyms:(2S,3S)-2,3-epoxy-5,5-dimethyl-6-(2-tetrahydropyranyloxy)-1-trityloxyhexane

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Chemical Property of (2S,3S)-2,3-epoxy-5,5-dimethyl-6-(2-tetrahydropyranyloxy)-1-trityloxyhexane

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Technology Process of (2S,3S)-2,3-epoxy-5,5-dimethyl-6-(2-tetrahydropyranyloxy)-1-trityloxyhexane

There total 7 articles about (2S,3S)-2,3-epoxy-5,5-dimethyl-6-(2-tetrahydropyranyloxy)-1-trityloxyhexane 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: 85.0%

: 76-83-5
trityl chloride

: 137532-06-0
{(2S,3S)-3-[2,2-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-oxiranyl}-methanol

: 155433-50-4
(2S,3S)-2,3-epoxy-5,5-dimethyl-6-(2-tetrahydropyranyloxy)-1-trityloxyhexane

Guidance literature:: With dmap; triethylamine; In dichloromethane; for 10h; Ambient temperature;
DOI:10.1016/S0040-4020(01)81547-7

Reference yield:

: 5497-67-6
2,2-dimethyl-4-pentenal

: 155433-50-4
(2S,3S)-2,3-epoxy-5,5-dimethyl-6-(2-tetrahydropyranyloxy)-1-trityloxyhexane

Guidance literature:: Multi-step reaction with 7 steps

1: NaBH₄

2: TsOH

3: 83 percent / OsO₄, NaIO₄ / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 3 h / 50 °C

4: 1.) NaH / 1.) THF, room temp., 30 min, 2.) THF, -78 deg C, 1 h

5: 95 percent / diisobutyl aluminum hydride / CH₂Cl₂; hexane / 0.5 h / -78 °C

6: 86 percent / (+)-diisopropyl tartrate, titanium tetraisopropoxide, t-butyl hydroperoxide, MS 4 Angstroem / CH₂Cl₂; toluene / 11.5 h / -20 °C

7: 85 percent / triethylamine, 4-DMAP / CH₂Cl₂ / 10 h / Ambient temperature

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; L-(+)-diisopropyl tartrate; MS 4 Angstroem; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; hexane; dichloromethane; water; toluene; tert-butyl alcohol;
DOI:10.1016/S0040-4020(01)81547-7

Reference yield:

: 3420-42-6
2,2-dimethylpent-4-en-1-ol

: 155433-50-4
(2S,3S)-2,3-epoxy-5,5-dimethyl-6-(2-tetrahydropyranyloxy)-1-trityloxyhexane

Guidance literature:: Multi-step reaction with 6 steps

1: TsOH

2: 83 percent / OsO₄, NaIO₄ / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 3 h / 50 °C

3: 1.) NaH / 1.) THF, room temp., 30 min, 2.) THF, -78 deg C, 1 h

4: 95 percent / diisobutyl aluminum hydride / CH₂Cl₂; hexane / 0.5 h / -78 °C

5: 86 percent / (+)-diisopropyl tartrate, titanium tetraisopropoxide, t-butyl hydroperoxide, MS 4 Angstroem / CH₂Cl₂; toluene / 11.5 h / -20 °C

6: 85 percent / triethylamine, 4-DMAP / CH₂Cl₂ / 10 h / Ambient temperature

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium periodate; osmium(VIII) oxide; L-(+)-diisopropyl tartrate; MS 4 Angstroem; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; hexane; dichloromethane; water; toluene; tert-butyl alcohol;
DOI:10.1016/S0040-4020(01)81547-7