(S)-6-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-5,6-dihydro-pyran-2-one

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Chemical Name:(S)-6-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-5,6-dihydro-pyran-2-one
CAS No.:562823-61-4
Molecular Formula:C₁₉H₂₄O₅
Molecular Weight:332.397
Hs Code.:

Synonyms:(S)-6-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-5,6-dihydro-pyran-2-one

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Chemical Property of (S)-6-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-5,6-dihydro-pyran-2-one

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Technology Process of (S)-6-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-5,6-dihydro-pyran-2-one

There total 11 articles about (S)-6-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-5,6-dihydro-pyran-2-one 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: 90.0%

: 562823-60-3
Acrylic acid (S)-1-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-but-3-enyl ester

: 562823-61-4
(S)-6-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-5,6-dihydro-pyran-2-one

Guidance literature:: Grubbs catalyst first generation; In dichloromethane; at 40 ℃; for 14h;
DOI:10.1016/S0040-4039(03)00744-5

Reference yield:

: 256494-25-4
(E)-ethyl 5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)pent-2-enoate

: 562823-61-4
(S)-6-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-5,6-dihydro-pyran-2-one

Guidance literature:: Multi-step reaction with 9 steps

1: AD mix-α; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 36 h / 0 °C

2: 92 percent / PPTS / acetone / 5 h / 23 °C

3: 97 percent / LiBH₄ / tetrahydrofuran / 2 h / 0 °C

4: 69 percent / NaH / dimethylformamide / 4 h / 23 °C

5: 99 percent / n-Bu₄N⁽¹⁺⁾*F^(1-) / tetrahydrofuran / 2 h / 23 °C

6: 87 percent / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 2 h / 23 °C

7: 71 percent / tetrahydrofuran / 3 h / -78 °C

8: 62 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

9: 90 percent / Cl₂(PCy₃)2Ru=CHPh / CH₂Cl₂ / 14 h / 40 °C

With AD-mix-α; lithium borohydride; methanesulfonamide; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 1: Sharpless asymmetric dihydroxylation / 6: Dess-Martin oxidation / 7: Brown's allylboration;
DOI:10.1016/S0040-4039(03)00744-5

Reference yield:

: 562823-57-8
[2-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-tert-butyl-diphenyl-silane

: 562823-61-4
(S)-6-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-5,6-dihydro-pyran-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: 99 percent / n-Bu₄N⁽¹⁺⁾*F^(1-) / tetrahydrofuran / 2 h / 23 °C

2: 87 percent / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 2 h / 23 °C

3: 71 percent / tetrahydrofuran / 3 h / -78 °C

4: 62 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

5: 90 percent / Cl₂(PCy₃)2Ru=CHPh / CH₂Cl₂ / 14 h / 40 °C

With tetrabutyl ammonium fluoride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane; 2: Dess-Martin oxidation / 3: Brown's allylboration;
DOI:10.1016/S0040-4039(03)00744-5