DL-1,2-di-O-acetyl-(1,3/2,6)-3-acetamidomethyl-6-(p-toluenesulfonamido)-4-cyclohexene-1,2-diol

Base Information

Chemical Name:DL-1,2-di-O-acetyl-(1,3/2,6)-3-acetamidomethyl-6-(p-toluenesulfonamido)-4-cyclohexene-1,2-diol
CAS No.:80065-51-6
Molecular Formula:C₂₀H₂₆N₂O₇S
Molecular Weight:438.502
Hs Code.:

Synonyms:DL-1,2-di-O-acetyl-(1,3/2,6)-3-acetamidomethyl-6-(p-toluenesulfonamido)-4-cyclohexene-1,2-diol

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Chemical Property of DL-1,2-di-O-acetyl-(1,3/2,6)-3-acetamidomethyl-6-(p-toluenesulfonamido)-4-cyclohexene-1,2-diol

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Technology Process of DL-1,2-di-O-acetyl-(1,3/2,6)-3-acetamidomethyl-6-(p-toluenesulfonamido)-4-cyclohexene-1,2-diol

There total 7 articles about DL-1,2-di-O-acetyl-(1,3/2,6)-3-acetamidomethyl-6-(p-toluenesulfonamido)-4-cyclohexene-1,2-diol 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: 59.0%

: 127-09-3
sodium acetate

: 80065-47-0
DL-3,4-di-O-acetyl-1-O-methylsulfonyl-(1,2,4/3,5)-5-acetamidomethyl-2-(p-toluenesulfonamido)-1,3,4-cyclohexanetriol

: 80065-51-6
DL-1,2-di-O-acetyl-(1,3/2,6)-3-acetamidomethyl-6-(p-toluenesulfonamido)-4-cyclohexene-1,2-diol

Guidance literature:: In N,N-dimethyl-formamide; at 80 ℃; for 48h;
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

: 80065-51-6
DL-1,2-di-O-acetyl-(1,3/2,6)-3-acetamidomethyl-6-(p-toluenesulfonamido)-4-cyclohexene-1,2-diol

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

6: 59 percent / dimethylformamide / 48 h / 80 °C

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

: 80065-51-6
DL-1,2-di-O-acetyl-(1,3/2,6)-3-acetamidomethyl-6-(p-toluenesulfonamido)-4-cyclohexene-1,2-diol

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

5: 59 percent / dimethylformamide / 48 h / 80 °C

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