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

Base Information

Chemical Name:7R,8R-dibenzyloxy-2S-(2-iodoethyl)-8R-methyltetrahydropyrano[3R,4R-b][1,4]dioxin-3-one
CAS No.:569660-81-7
Molecular Formula:C₂₄H₂₇IO₆
Molecular Weight:538.379
Hs Code.:

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

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

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

There total 12 articles about 7R,8R-dibenzyloxy-2S-(2-iodoethyl)-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:

: 569661-48-9
7R,8R-dibenzyloxy-2S-(2-hydroxy-ethyl)-8R-methyltetrahydropyrano[3R,4R-b][1,4]dioxin-3-one

: 569660-81-7
7R,8R-dibenzyloxy-2S-(2-iodoethyl)-8R-methyltetrahydropyrano[3R,4R-b][1,4]dioxin-3-one

Guidance literature:: With 2,6-dimethylpyridine; iodine; triphenylphosphine; In dichloromethane; at 20 ℃; for 4h;
DOI:10.1021/ja029225v

Reference yield:

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

: 569660-81-7
7R,8R-dibenzyloxy-2S-(2-iodoethyl)-8R-methyltetrahydropyrano[3R,4R-b][1,4]dioxin-3-one

Guidance literature:: Multi-step reaction with 10 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

9.1: sodium cyanoborohydride; acetic acid / tetrahydrofuran / 0.33 h / 20 °C

10.1: 1.553 g / iodine; triphenylphosphine; 2,6-lutidine / CH₂Cl₂ / 4 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; osmium(VIII) oxide; cerium(III) chloride; sulfuric acid; camphor-10-sulfonic acid; iodine; sodium hydride; di(n-butyl)tin oxide; sodium cyanoborohydride; sodium hydrogencarbonate; acetic acid; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;
DOI:10.1021/ja029225v

Reference yield:

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

: 569660-81-7
7R,8R-dibenzyloxy-2S-(2-iodoethyl)-8R-methyltetrahydropyrano[3R,4R-b][1,4]dioxin-3-one

Guidance literature:: Multi-step reaction with 12 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

11.1: sodium cyanoborohydride; acetic acid / tetrahydrofuran / 0.33 h / 20 °C

12.1: 1.553 g / iodine; triphenylphosphine; 2,6-lutidine / CH₂Cl₂ / 4 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; osmium(VIII) oxide; cerium(III) chloride; oxalyl dichloride; (+/-)camphorsulfonic acid; sulfuric acid; camphor-10-sulfonic acid; iodine; sodium hydride; di(n-butyl)tin oxide; sodium cyanoborohydride; sodium hydrogencarbonate; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; 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