(7R,8R-dibenzyloxy-8R-methyl-3-oxohexahydropyrano[3R,4R-b][1,4]dioxin-2S-yl)acetaldehyde

Base Information

Chemical Name:(7R,8R-dibenzyloxy-8R-methyl-3-oxohexahydropyrano[3R,4R-b][1,4]dioxin-2S-yl)acetaldehyde
CAS No.:569661-46-7
Molecular Formula:C₂₄H₂₆O₇
Molecular Weight:426.466
Hs Code.:

Synonyms:(7R,8R-dibenzyloxy-8R-methyl-3-oxohexahydropyrano[3R,4R-b][1,4]dioxin-2S-yl)acetaldehyde

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Chemical Property of (7R,8R-dibenzyloxy-8R-methyl-3-oxohexahydropyrano[3R,4R-b][1,4]dioxin-2S-yl)acetaldehyde

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Technology Process of (7R,8R-dibenzyloxy-8R-methyl-3-oxohexahydropyrano[3R,4R-b][1,4]dioxin-2S-yl)acetaldehyde

There total 10 articles about (7R,8R-dibenzyloxy-8R-methyl-3-oxohexahydropyrano[3R,4R-b][1,4]dioxin-2S-yl)acetaldehyde 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: 97.0%

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

: 569661-46-7
(7R,8R-dibenzyloxy-8R-methyl-3-oxohexahydropyrano[3R,4R-b][1,4]dioxin-2S-yl)acetaldehyde

Guidance literature:: 2S-allyl-7R,8R-dibenzyloxy-8R-methyltetrahydropyrano[3R,4R-b][1,4]dioxin-3-one; With osmium(VIII) oxide; sodium hydrogencarbonate; In diethyl ether; tert-butyl alcohol; at 20 ℃; for 0.0833333h;

With sodium periodate; In diethyl ether; tert-butyl alcohol; at 20 ℃; for 3.5h;
DOI:10.1021/ja029225v

Reference yield:

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

: 569661-46-7
(7R,8R-dibenzyloxy-8R-methyl-3-oxohexahydropyrano[3R,4R-b][1,4]dioxin-2S-yl)acetaldehyde

Guidance literature:: Multi-step reaction with 8 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

8.1: osmium tetroxide; aq. sodium bicarbonate / diethyl ether; 2-methyl-propan-2-ol / 0.08 h / 20 °C

8.2: 97 percent / aq. NaIO₄ / diethyl ether; 2-methyl-propan-2-ol / 3.5 h / 20 °C

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

Reference yield:

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

: 569661-46-7
(7R,8R-dibenzyloxy-8R-methyl-3-oxohexahydropyrano[3R,4R-b][1,4]dioxin-2S-yl)acetaldehyde

Guidance literature:: Multi-step reaction with 10 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

10.1: osmium tetroxide; aq. sodium bicarbonate / diethyl ether; 2-methyl-propan-2-ol / 0.08 h / 20 °C

10.2: 97 percent / aq. NaIO₄ / diethyl ether; 2-methyl-propan-2-ol / 3.5 h / 20 °C

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