O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-(1->6)-1,5-anhydro-3,4-di-O-benzyl-2-deoxy-D-arabino-hex-1-enopyranose

Base Information

Chemical Name:O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-(1->6)-1,5-anhydro-3,4-di-O-benzyl-2-deoxy-D-arabino-hex-1-enopyranose
CAS No.:121654-08-8
Molecular Formula:C₅₄H₅₆O₉
Molecular Weight:849.033
Hs Code.:

Synonyms:O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-(1->6)-1,5-anhydro-3,4-di-O-benzyl-2-deoxy-D-arabino-hex-1-enopyranose

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Chemical Property of O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-(1->6)-1,5-anhydro-3,4-di-O-benzyl-2-deoxy-D-arabino-hex-1-enopyranose

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Technology Process of O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-(1->6)-1,5-anhydro-3,4-di-O-benzyl-2-deoxy-D-arabino-hex-1-enopyranose

There total 3 articles about O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-(1->6)-1,5-anhydro-3,4-di-O-benzyl-2-deoxy-D-arabino-hex-1-enopyranose 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: 95.0%

: 100-39-0
benzyl bromide

: 121654-06-6
O-(3,4,6-Tri-O-benzyl-β-D-glucopyranosyl)-(1->6)-1,5-anhydro-3,4-di-O-benzyl-2-deoxy-D-arabino-hex-1-enopyranose

: 121654-08-8
O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-(1->6)-1,5-anhydro-3,4-di-O-benzyl-2-deoxy-D-arabino-hex-1-enopyranose

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 12h; Inert atmosphere;
DOI:10.1021/jo500032k

Reference yield:

: 55628-54-1
3,4,6-tri-O-benzyl-D-glucal

: 121654-08-8
O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-(1->6)-1,5-anhydro-3,4-di-O-benzyl-2-deoxy-D-arabino-hex-1-enopyranose

Guidance literature:: Multi-step reaction with 3 steps

1: dimethyldioxirane / CH₂Cl₂; acetone / 1 h / 0 °C

2: 56 percent / ZnCl₂ / tetrahydrofuran; diethyl ether / 1.) -78 deg C, 1 h, 2.) -78 deg C -> r.t., 1 h; r.t., 18 h

3: 1.) NaH / 1.) DMF, 0 deg C, 1 h, 2.) 0 deg C, 1 h; r.t., 1 h

With 3,3-dimethyldioxirane; sodium hydride; zinc(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; acetone;
DOI:10.1021/ja00199a028

Reference yield:

: 74372-90-0
3,4,6-tri-O-benzyl-D-glucal epoxide

: 121654-08-8
O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-(1->6)-1,5-anhydro-3,4-di-O-benzyl-2-deoxy-D-arabino-hex-1-enopyranose

Guidance literature:: Multi-step reaction with 2 steps

1: 56 percent / ZnCl₂ / tetrahydrofuran; diethyl ether / 1.) -78 deg C, 1 h, 2.) -78 deg C -> r.t., 1 h; r.t., 18 h

2: 1.) NaH / 1.) DMF, 0 deg C, 1 h, 2.) 0 deg C, 1 h; r.t., 1 h

With sodium hydride; zinc(II) chloride; In tetrahydrofuran; diethyl ether;
DOI:10.1021/ja00199a028