DL-1,2-di-O-acetyl-(1,3/2,6)-3-acetamidomethyl-6-(p-toluenesulfonamido)-1,2-cyclohexanediol

Base Information

Chemical Name:DL-1,2-di-O-acetyl-(1,3/2,6)-3-acetamidomethyl-6-(p-toluenesulfonamido)-1,2-cyclohexanediol
CAS No.:80065-49-2
Molecular Formula:C₂₀H₂₈N₂O₇S
Molecular Weight:440.518
Hs Code.:

Synonyms:DL-1,2-di-O-acetyl-(1,3/2,6)-3-acetamidomethyl-6-(p-toluenesulfonamido)-1,2-cyclohexanediol

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Chemical Property of DL-1,2-di-O-acetyl-(1,3/2,6)-3-acetamidomethyl-6-(p-toluenesulfonamido)-1,2-cyclohexanediol

Chemical Property:

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Technology Process of DL-1,2-di-O-acetyl-(1,3/2,6)-3-acetamidomethyl-6-(p-toluenesulfonamido)-1,2-cyclohexanediol

There total 7 articles about DL-1,2-di-O-acetyl-(1,3/2,6)-3-acetamidomethyl-6-(p-toluenesulfonamido)-1,2-cyclohexanediol 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: 66.0%

: 108-24-7
acetic anhydride

: DL-1,2-di-O-acetyl-(1,3/2,4,6)-4-azido-6-azidomethyl-3-(p-toluenesulfonamido)-1,2-cyclohexanediol

: 80065-49-2
DL-1,2-di-O-acetyl-(1,3/2,6)-3-acetamidomethyl-6-(p-toluenesulfonamido)-1,2-cyclohexanediol

: 80065-48-1
DL-1,2-di-O-acetyl-(1,3/2,4,6)-4-acetamido-6-acetamidomethyl-3-(p-toluenesulfonamido)-1,2-cyclohexanediol

Guidance literature:: With hydrogen; Raney nickel T-4; In methanol; under 2584 Torr;
DOI:10.1246/bcsj.54.2739

Reference yield:

: 69982-70-3,87100-11-6,96291-85-9,115225-41-7
3,4-di-O-acetyl-2,6-dibromo-2,6-dideoxy-5a-carba-β-DL-glucopyranosyl bromide

: 80065-49-2
DL-1,2-di-O-acetyl-(1,3/2,6)-3-acetamidomethyl-6-(p-toluenesulfonamido)-1,2-cyclohexanediol

Guidance literature:: Multi-step reaction with 6 steps

1: 92 percent / zinc dust, acetic acid / 0.17 h / 70 °C

2: 31 percent / osmium tetroxide, triethylbenzylammonium chloride / CHCl₃; H₂O; 2-methyl-propan-2-ol / 40 h / 60 °C

3: 69 percent / pyridine / 0 °C

4: 68 percent / sodium azide / dimethylformamide / 2 h / 80 °C

5: 71 percent / sodium azide / dimethylformamide / 20 h / 85 °C

6: 18 percent / H₂ / Raney nickel T-4 / methanol / 2584 Torr

With pyridine; osmium(VIII) oxide; sodium azide; N-benzyl-N,N,N-triethylammonium chloride; hydrogen; acetic acid; zinc; Raney nickel T-4; In methanol; chloroform; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1246/bcsj.54.2739

Reference yield:

: 127-65-1
chloroamine-T

: 80065-49-2
DL-1,2-di-O-acetyl-(1,3/2,6)-3-acetamidomethyl-6-(p-toluenesulfonamido)-1,2-cyclohexanediol

Guidance literature:: Multi-step reaction with 5 steps

1: 31 percent / osmium tetroxide, triethylbenzylammonium chloride / CHCl₃; H₂O; 2-methyl-propan-2-ol / 40 h / 60 °C

2: 69 percent / pyridine / 0 °C

3: 68 percent / sodium azide / dimethylformamide / 2 h / 80 °C

4: 71 percent / sodium azide / dimethylformamide / 20 h / 85 °C

5: 18 percent / H₂ / Raney nickel T-4 / methanol / 2584 Torr

With pyridine; osmium(VIII) oxide; sodium azide; N-benzyl-N,N,N-triethylammonium chloride; hydrogen; Raney nickel T-4; In methanol; chloroform; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1246/bcsj.54.2739