(2S,3S)-Toluene-4-sulfonic acid 2-methyl-3-[3-methyl-3-(tetrahydropyran-2-yloxy)butyl]oxiranylmethyl ester

Base Information

Chemical Name:(2S,3S)-Toluene-4-sulfonic acid 2-methyl-3-[3-methyl-3-(tetrahydropyran-2-yloxy)butyl]oxiranylmethyl ester
CAS No.:902451-94-9
Molecular Formula:C₂₁H₃₂O₆S
Molecular Weight:412.547
Hs Code.:

Synonyms:(2S,3S)-Toluene-4-sulfonic acid 2-methyl-3-[3-methyl-3-(tetrahydropyran-2-yloxy)butyl]oxiranylmethyl ester

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Chemical Property of (2S,3S)-Toluene-4-sulfonic acid 2-methyl-3-[3-methyl-3-(tetrahydropyran-2-yloxy)butyl]oxiranylmethyl ester

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Technology Process of (2S,3S)-Toluene-4-sulfonic acid 2-methyl-3-[3-methyl-3-(tetrahydropyran-2-yloxy)butyl]oxiranylmethyl ester

There total 9 articles about (2S,3S)-Toluene-4-sulfonic acid 2-methyl-3-[3-methyl-3-(tetrahydropyran-2-yloxy)butyl]oxiranylmethyl 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: 92.0%

: 98-59-9
p-toluenesulfonyl chloride

: 360066-66-6
(2S,3S)-{2-Methyl-3-[3-methyl-3-(tetrahydropyran-2-yloxy)butyl]oxiranyl}methanol

: 902451-94-9
(2S,3S)-Toluene-4-sulfonic acid 2-methyl-3-[3-methyl-3-(tetrahydropyran-2-yloxy)butyl]oxiranylmethyl ester

Guidance literature:: With pyridine; at 0 - 5 ℃; for 12h;

Reference yield:

: 3123-97-5
dihydro-5,5-dimethyl-2(3H)-furanone

: 902451-94-9
(2S,3S)-Toluene-4-sulfonic acid 2-methyl-3-[3-methyl-3-(tetrahydropyran-2-yloxy)butyl]oxiranylmethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 88 percent / DIBAL-H / CH₂Cl₂; toluene / 0.75 h / -20 °C

2: benzene / 12 h / Heating

3: 99 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 3 h / 20 °C

4: 83 percent / DIBAL-H / CH₂Cl₂; toluene / 0.75 h / -20 °C

5: 63 percent / L-(+)DET; Ti(i-PrO)4; tert-butyl hydroperoxide / CH₂Cl₂; toluene / 12 h / -23 °C

6: 92 percent / pyridine / 12 h / 0 - 5 °C

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; In dichloromethane; toluene; benzene; 2: Wittig olefination / 5: Sharpless epoxidation;

Reference yield:

: 14092-32-1
2-methyl-5-<(tetrahydro-2H-pyran-2-yl)-oxy>-3-pentyn-2-ol

: 902451-94-9
(2S,3S)-Toluene-4-sulfonic acid 2-methyl-3-[3-methyl-3-(tetrahydropyran-2-yloxy)butyl]oxiranylmethyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 90 percent / p-TsOH / methanol / 1 h / 20 °C

2: 93 percent / H₂ / 10 percent Pd/C / ethyl acetate / 3 h / 20 °C

3: 88 percent / PDC / dimethylformamide / 3 h / 20 °C

4: 88 percent / DIBAL-H / CH₂Cl₂; toluene / 0.75 h / -20 °C

5: benzene / 12 h / Heating

6: 99 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 3 h / 20 °C

7: 83 percent / DIBAL-H / CH₂Cl₂; toluene / 0.75 h / -20 °C

8: 63 percent / L-(+)DET; Ti(i-PrO)4; tert-butyl hydroperoxide / CH₂Cl₂; toluene / 12 h / -23 °C

9: 92 percent / pyridine / 12 h / 0 - 5 °C

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dipyridinium dichromate; diethyl (2R,3R)-tartrate; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; toluene-4-sulfonic acid; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; benzene; 5: Wittig olefination / 8: Sharpless epoxidation;