(2S,4R,5S)-4-((2S,3S)-3-Hydroxymethyl-3-methyl-oxiranylmethyl)-2-phenyl-[1,3]dioxan-5-ol

Base Information

Chemical Name:(2S,4R,5S)-4-((2S,3S)-3-Hydroxymethyl-3-methyl-oxiranylmethyl)-2-phenyl-[1,3]dioxan-5-ol
CAS No.:1053634-48-2
Molecular Formula:C₁₅H₂₀O₅
Molecular Weight:280.321
Hs Code.:

Synonyms:(2S,4R,5S)-4-((2S,3S)-3-Hydroxymethyl-3-methyl-oxiranylmethyl)-2-phenyl-[1,3]dioxan-5-ol

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Chemical Property of (2S,4R,5S)-4-((2S,3S)-3-Hydroxymethyl-3-methyl-oxiranylmethyl)-2-phenyl-[1,3]dioxan-5-ol

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Technology Process of (2S,4R,5S)-4-((2S,3S)-3-Hydroxymethyl-3-methyl-oxiranylmethyl)-2-phenyl-[1,3]dioxan-5-ol

There total 1 articles about (2S,4R,5S)-4-((2S,3S)-3-Hydroxymethyl-3-methyl-oxiranylmethyl)-2-phenyl-[1,3]dioxan-5-ol 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: 100.0%

: {(2S,3S)-3-[(2S,4R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-ylmethyl]-2-methyl-oxiranyl}-methanol

: 1053634-48-2
(2S,4R,5S)-4-((2S,3S)-3-Hydroxymethyl-3-methyl-oxiranylmethyl)-2-phenyl-[1,3]dioxan-5-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;
DOI:10.1021/ol016355k

Reference yield: 100.0%

: 1053634-48-2
(2S,4R,5S)-4-((2S,3S)-3-Hydroxymethyl-3-methyl-oxiranylmethyl)-2-phenyl-[1,3]dioxan-5-ol

: 361534-73-8
(2S,4aS,6R,7S,8aR)-6-Hydroxymethyl-6-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

Guidance literature:: With pyridinium p-toluenesulfonate; In dichloromethane; at 20 ℃;
DOI:10.1021/ol016355k

Reference yield:

: 1053634-48-2
(2S,4R,5S)-4-((2S,3S)-3-Hydroxymethyl-3-methyl-oxiranylmethyl)-2-phenyl-[1,3]dioxan-5-ol

: (2S,4aS,5aR,6aS,7aR,11aS,12aR,13aS,14aR)-5a,6a,7a-Trimethyl-2-phenyl-dodecahydro-1,3,5,7,11,13-hexaoxa-pentacen-10-one

Guidance literature:: Multi-step reaction with 24 steps

1.1: 100 percent / PPTS / CH₂Cl₂ / 20 °C

2.1: 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

3.1: CH₂Cl₂ / 3 h / -78 - 0 °C

4.1: 1.33 g / molecular sieves 4 A / dimethylsulfoxide / 0.67 h / 80 °C

5.1: 87 percent / DIBAH / CH₂Cl₂; hexane / 1 h / -78 °C

6.1: 89 percent / tetrahydrofuran / 1 h / 0 - 20 °C

7.1: N-methylmorpholine N-oxide; molecular sieves 4 A / CH₂Cl₂ / 0.75 h / 20 °C

7.2: 93 percent / tetrapropylammonium perruthenate / CH₂Cl₂ / 1.5 h / 20 °C

8.1: 487 mg / n-Bu₄NF*xH₂O / tetrahydrofuran / 2.5 h / 20 °C

9.1: 544 mg / N-methylmorpholine / CH₂Cl₂ / 6 h / 20 °C

10.1: 99 percent / SmI₂ / methanol; tetrahydrofuran / 0.08 h / 0 °C

11.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

12.1: 513 mg / DIBAH / toluene; hexane / 0.25 h / -78 °C

13.1: 565 mg / toluene / 100 °C

14.1: 480 mg / DIBAH / toluene; hexane / 0.17 h / -78 °C

15.1: (+)-diethyl L-tartrate; Ti(O-i-Pr)4 / CH₂Cl₂ / 0.33 h / -20 °C

15.2: 100 percent / t-BuOOH / CH₂Cl₂ / 22 h / -20 °C

16.1: N-methylmorpholine N-oxide; molecular sieves 4 A / CH₂Cl₂ / 0.25 h / 20 °C

16.2: 56.2 mg / tetrapropylammonium perruthenate / CH₂Cl₂ / 0.5 h / 20 °C

17.1: NaN(TMS)2 / tetrahydrofuran / 0.33 h / 0 °C

17.2: 42.8 mg / tetrahydrofuran / 0.25 h / 0 °C

18.1: 99 percent / n-Bu₄NF / tetrahydrofuran / 0.5 h / 20 °C

19.1: 74 percent / 10-camphorsulfonic acid / toluene / 3.5 h / 0 °C

20.1: O₃ / CH₂Cl₂ / 0.02 h / -78 °C

21.1: 11.5 mg / toluene / 1 h / 100 °C

22.1: H₂ / Pd/C / ethyl acetate / 2 h / 20 °C

23.1: LiOH / methanol; H₂O / 3.5 h / 20 °C

24.1: 5.3 mg / acetic anhydride; pyridine / 1.5 h / 20 °C

With 4-methyl-morpholine; pyridine; 2,6-dimethylpyridine; titanium(IV) isopropylate; lithium hydroxide; samarium diiodide; diethyl (2R,3R)-tartrate; 4 A molecular sieve; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; acetic anhydride; diisobutylaluminium hydride; ozone; 4-methylmorpholine N-oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; toluene; 6.1: Grignard reaction / 9.1: hetero-Michael reaction / 13.1: Wittig reaction / 17.2: Wittig reaction / 21.1: Wittig reaction;
DOI:10.1021/ol016355k