benzyl [2-1,3-dithiane-3-deoxy-4,5-7,8-di-O-isopropylidene-α-D-manno-octulopyranosid]onate

Base Information

Chemical Name:benzyl [2-1,3-dithiane-3-deoxy-4,5-7,8-di-O-isopropylidene-α-D-manno-octulopyranosid]onate
CAS No.:1392224-88-2
Molecular Formula:C₂₄H₃₄O₇S₂
Molecular Weight:498.662
Hs Code.:

Synonyms:benzyl [2-1,3-dithiane-3-deoxy-4,5-7,8-di-O-isopropylidene-α-D-manno-octulopyranosid]onate

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Chemical Property of benzyl [2-1,3-dithiane-3-deoxy-4,5-7,8-di-O-isopropylidene-α-D-manno-octulopyranosid]onate

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Technology Process of benzyl [2-1,3-dithiane-3-deoxy-4,5-7,8-di-O-isopropylidene-α-D-manno-octulopyranosid]onate

There total 3 articles about benzyl [2-1,3-dithiane-3-deoxy-4,5-7,8-di-O-isopropylidene-α-D-manno-octulopyranosid]onate 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: 58.0%

: 64114-00-7
benzyl 1,3-dithiane-2-carboxylate

: 127218-23-9
2,3-5,6-di-O-isopropylidene-1,4-O-sulfate-D-mannitol

: 1392224-88-2
benzyl [2-1,3-dithiane-3-deoxy-4,5-7,8-di-O-isopropylidene-α-D-manno-octulopyranosid]onate

Guidance literature:: benzyl 1,3-dithiane-2-carboxylate; With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane; In tetrahydrofuran; at -45 ℃; for 0.5h; Inert atmosphere;

2,3-5,6-di-O-isopropylidene-1,4-O-sulfate-D-mannitol; In tetrahydrofuran; at -45 - 20 ℃; for 1h; Inert atmosphere;
DOI:10.1021/ja306274v

Reference yield:

: 134623-61-3
2,3:5,6-di-O-isopropylidene-D-mannitol 1,4-sulfite

: 1392224-88-2
benzyl [2-1,3-dithiane-3-deoxy-4,5-7,8-di-O-isopropylidene-α-D-manno-octulopyranosid]onate

Guidance literature:: Multi-step reaction with 2 steps

1.1: ruthenium trichloride; sodium periodate; water / dichloromethane; acetonitrile

2.1: N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -45 °C / Inert atmosphere

2.2: 1 h / -45 - 20 °C / Inert atmosphere

With N,N,N,N,N,N-hexamethylphosphoric triamide; ruthenium trichloride; sodium periodate; water; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1021/ja306274v

Reference yield:

: 100-51-6,185532-71-2
benzyl alcohol

: 1392224-88-2
benzyl [2-1,3-dithiane-3-deoxy-4,5-7,8-di-O-isopropylidene-α-D-manno-octulopyranosid]onate

Guidance literature:: Multi-step reaction with 2 steps

1.1: water; toluene-4-sulfonic acid / toluene / 16 h / Inert atmosphere; Reflux

1.2: 6 h / Inert atmosphere; Reflux

2.1: N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -45 °C / Inert atmosphere

2.2: 1 h / -45 - 20 °C / Inert atmosphere

With N,N,N,N,N,N-hexamethylphosphoric triamide; water; toluene-4-sulfonic acid; lithium hexamethyldisilazane; In tetrahydrofuran; toluene;
DOI:10.1021/ja306274v