N-{(R)-1-[(4R,5R)-5-((R)-1,2-Dihydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-phenyl-ethyl}-4-methyl-benzenesulfonamide

Base Information

Chemical Name:N-{(R)-1-[(4R,5R)-5-((R)-1,2-Dihydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-phenyl-ethyl}-4-methyl-benzenesulfonamide
CAS No.:275813-02-0
Molecular Formula:C₂₂H₂₉NO₆S
Molecular Weight:435.541
Hs Code.:

Synonyms:N-{(R)-1-[(4R,5R)-5-((R)-1,2-Dihydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-phenyl-ethyl}-4-methyl-benzenesulfonamide

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Chemical Property of N-{(R)-1-[(4R,5R)-5-((R)-1,2-Dihydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-phenyl-ethyl}-4-methyl-benzenesulfonamide

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Technology Process of N-{(R)-1-[(4R,5R)-5-((R)-1,2-Dihydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-phenyl-ethyl}-4-methyl-benzenesulfonamide

There total 4 articles about N-{(R)-1-[(4R,5R)-5-((R)-1,2-Dihydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-phenyl-ethyl}-4-methyl-benzenesulfonamide 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%

: 275812-90-3
1,2-dideoxy-3,4:5,6-di-O-isopropylidene-1-C-phenyl-2-(N-p-toluenesulfonyl)amino-D-mannitol

: 275813-02-0
N-{(R)-1-[(4R,5R)-5-((R)-1,2-Dihydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-phenyl-ethyl}-4-methyl-benzenesulfonamide

Guidance literature:: With Dowex 50X₈-200; In methanol; at 20 ℃;
DOI:10.1016/S0040-4039(00)00130-1

Reference yield:

: 1-amino-1-deoxy-3,4;5,6-di-O-isopropylidene-D-glucitol p-toluenesulfonate

: 275813-02-0
N-{(R)-1-[(4R,5R)-5-((R)-1,2-Dihydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-phenyl-ethyl}-4-methyl-benzenesulfonamide

Guidance literature:: Multi-step reaction with 4 steps

1.1: p-TsCl; Et₃N / CH₂Cl₂ / 0.5 h / 20 °C

1.2: 92 percent / 1 h / 20 °C

2.1: 90 percent / sodium hydride / tetrahydrofuran / 1 h / 20 °C

3.1: 95 percent / CuI / tetrahydrofuran / 1 h / 20 °C

4.1: 82 percent / Dowex 50X₈-200 / aq. methanol / 20 °C

With copper(l) iodide; Dowex 50X₈-200; sodium hydride; triethylamine; p-toluenesulfonyl chloride; In tetrahydrofuran; methanol; dichloromethane; 1.1: Dehydration / 1.2: Esterification / 2.1: Cyclization / 3.1: Ring cleavage / 4.1: Hydrolysis;
DOI:10.1016/S0040-4039(00)00130-1

Reference yield:

: 275812-74-3
1,2-dideoxy-3,4:5,6-di-O-isopropylidene-1,2-(N-p-toluenesulfonyl)imino-D-mannitol

: 275813-02-0
N-{(R)-1-[(4R,5R)-5-((R)-1,2-Dihydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-phenyl-ethyl}-4-methyl-benzenesulfonamide

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / CuI / tetrahydrofuran / 1 h / 20 °C

2: 82 percent / Dowex 50X₈-200 / aq. methanol / 20 °C

With copper(l) iodide; Dowex 50X₈-200; In tetrahydrofuran; methanol; 1: Ring cleavage / 2: Hydrolysis;
DOI:10.1016/S0040-4039(00)00130-1