2S-allyl-7R,8R-dibenzyloxy-8R-methyltetrahydropyrano[3R,4R-b][1,4]dioxin-3-one

Base Information

Chemical Name:2S-allyl-7R,8R-dibenzyloxy-8R-methyltetrahydropyrano[3R,4R-b][1,4]dioxin-3-one
CAS No.:569660-88-4
Molecular Formula:C₂₅H₂₈O₆
Molecular Weight:424.494
Hs Code.:

Synonyms:2S-allyl-7R,8R-dibenzyloxy-8R-methyltetrahydropyrano[3R,4R-b][1,4]dioxin-3-one

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Chemical Property of 2S-allyl-7R,8R-dibenzyloxy-8R-methyltetrahydropyrano[3R,4R-b][1,4]dioxin-3-one

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Technology Process of 2S-allyl-7R,8R-dibenzyloxy-8R-methyltetrahydropyrano[3R,4R-b][1,4]dioxin-3-one

There total 9 articles about 2S-allyl-7R,8R-dibenzyloxy-8R-methyltetrahydropyrano[3R,4R-b][1,4]dioxin-3-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: 83.0%

: 556-56-9
allyl iodid

: 569660-86-2
7R,8R-dibenzyloxy-8R-methyltetrahydropyrano[3R,4R-b][1,4]dioxin-3-one

: 2R-allyl-7R,8R-dibenzyloxy-8R-methyltetrahydropyrano[3R,4R-b][1,4]dioxin-3-one

: 569660-88-4
2S-allyl-7R,8R-dibenzyloxy-8R-methyltetrahydropyrano[3R,4R-b][1,4]dioxin-3-one

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 3.5h;
DOI:10.1021/ja029225v

Reference yield:

: 28070-06-6
benzyl-3,4-O-isopropylidene-β-D-erythro-pentoribopyranosid-2-ulose

: 569660-88-4
2S-allyl-7R,8R-dibenzyloxy-8R-methyltetrahydropyrano[3R,4R-b][1,4]dioxin-3-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: cerium trichloride / tetrahydrofuran; diethyl ether / 4 h / -20 °C

2.1: sodium hydride; imidazole / dimethylformamide / 0.33 h / 0 °C

2.2: dimethylformamide / 1 h / 20 °C

3.1: 38.65 g / (+/-)-camphorsulfonic acid / methanol / 1 h

4.1: di-n-butyltin oxide / tetrahydrofuran / 1 h / Heating

4.2: tetra-n-butylammonium iodide; sodium hydroxide / dimethylformamide / 3 h / 20 °C

4.3: 1.35 g / aq. NaOH / dimethylformamide; diethyl ether / 1 h

5.1: sodium hydride / dimethylformamide / 0.5 h / 20 °C

5.2: 0.360 g / dimethylformamide / 2 h

6.1: 0.049 g / sulfuric acid / acetonitrile / 0.5 h / 20 °C

7.1: 83 percent / LDA / tetrahydrofuran; hexane / 3.5 h / -78 °C

With 1H-imidazole; cerium(III) chloride; sulfuric acid; camphor-10-sulfonic acid; sodium hydride; di(n-butyl)tin oxide; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja029225v

Reference yield:

: 5329-50-0
(-)-benzyl β-D-arabinopyranoside

: 569660-88-4
2S-allyl-7R,8R-dibenzyloxy-8R-methyltetrahydropyrano[3R,4R-b][1,4]dioxin-3-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: (+/-)camphorsulfonic acid / acetone / 1 h / 25 °C

2.1: oxalyl chloride; dimethylsulfoxide; triethylamine / CH₂Cl₂ / -78 - 0 °C

3.1: cerium trichloride / tetrahydrofuran; diethyl ether / 4 h / -20 °C

4.1: sodium hydride; imidazole / dimethylformamide / 0.33 h / 0 °C

4.2: dimethylformamide / 1 h / 20 °C

5.1: 38.65 g / (+/-)-camphorsulfonic acid / methanol / 1 h

6.1: di-n-butyltin oxide / tetrahydrofuran / 1 h / Heating

6.2: tetra-n-butylammonium iodide; sodium hydroxide / dimethylformamide / 3 h / 20 °C

6.3: 1.35 g / aq. NaOH / dimethylformamide; diethyl ether / 1 h

7.1: sodium hydride / dimethylformamide / 0.5 h / 20 °C

7.2: 0.360 g / dimethylformamide / 2 h

8.1: 0.049 g / sulfuric acid / acetonitrile / 0.5 h / 20 °C

9.1: 83 percent / LDA / tetrahydrofuran; hexane / 3.5 h / -78 °C

With 1H-imidazole; cerium(III) chloride; oxalyl dichloride; (+/-)camphorsulfonic acid; sulfuric acid; camphor-10-sulfonic acid; sodium hydride; di(n-butyl)tin oxide; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile; 2.1: Swern oxidation;
DOI:10.1021/ja029225v