3,6-di-O-benzyl-4-deoxy-D-glucal

Base Information

Chemical Name:3,6-di-O-benzyl-4-deoxy-D-glucal
CAS No.:1279711-36-2
Molecular Formula:C₂₀H₂₂O₃
Molecular Weight:310.393
Hs Code.:

Synonyms:3,6-di-O-benzyl-4-deoxy-D-glucal

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Chemical Property of 3,6-di-O-benzyl-4-deoxy-D-glucal

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Technology Process of 3,6-di-O-benzyl-4-deoxy-D-glucal

There total 6 articles about 3,6-di-O-benzyl-4-deoxy-D-glucal 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: 82.0%

: 75-15-0,12122-00-8
carbon disulfide

: 145852-76-2
3,6-di-O-benzyl-D-glucal

: 74-88-4
methyl iodide

: 1279711-36-2
3,6-di-O-benzyl-4-deoxy-D-glucal

Guidance literature:: carbon disulfide; 3,6-di-O-benzyl-D-glucal; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; for 0.75h;

methyl iodide; In tetrahydrofuran; mineral oil; at 20 ℃; for 16h;

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 0.25h; Reflux;
DOI:10.1021/jo102382r

Reference yield:

: 312623-79-3
(4aR,8R,8aS)-2-(4-methoxyphenyl)-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxin-8-ol

: 1279711-36-2
3,6-di-O-benzyl-4-deoxy-D-glucal

Guidance literature:: Multi-step reaction with 5 steps

1.1: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide; mineral oil / 20 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / hexane; dichloromethane / 2 h / 0 °C

3.1: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide; mineral oil / 20 °C / Inert atmosphere

4.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; tert-butyl alcohol / 3 h / 0 - 20 °C / pH 7 / aq. phosphate buffer

5.1: sodium hydride / tetrahydrofuran; mineral oil / 0.75 h / 0 - 20 °C

5.2: 16 h / 20 °C

5.3: 0.25 h / Reflux

With water; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; mineral oil; tert-butyl alcohol; 5.1: Barton-McCombie deoxygenation / 5.2: Barton-McCombie deoxygenation / 5.3: Barton-McCombie deoxygenation;
DOI:10.1021/jo102382r

Reference yield:

: 100-39-0
benzyl bromide

: 1279711-36-2
3,6-di-O-benzyl-4-deoxy-D-glucal

Guidance literature:: Multi-step reaction with 5 steps

1.1: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide; mineral oil / 20 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / hexane; dichloromethane / 2 h / 0 °C

3.1: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide; mineral oil / 20 °C / Inert atmosphere

4.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; tert-butyl alcohol / 3 h / 0 - 20 °C / pH 7 / aq. phosphate buffer

5.1: sodium hydride / tetrahydrofuran; mineral oil / 0.75 h / 0 - 20 °C

5.2: 16 h / 20 °C

5.3: 0.25 h / Reflux

With water; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; mineral oil; tert-butyl alcohol; 5.1: Barton-McCombie deoxygenation / 5.2: Barton-McCombie deoxygenation / 5.3: Barton-McCombie deoxygenation;
DOI:10.1021/jo102382r