1L-(1,2,4/3,5)-1-C-(acetoxymethyl)-2,3,4-tri-O-acetyl-5-azido-1,2,3,4-cyclohexanetetrol

Base Information

Chemical Name:1L-(1,2,4/3,5)-1-C-(acetoxymethyl)-2,3,4-tri-O-acetyl-5-azido-1,2,3,4-cyclohexanetetrol
CAS No.:694527-30-5
Molecular Formula:C₁₅H₂₁N₃O₉
Molecular Weight:387.346
Hs Code.:

Synonyms:1L-(1,2,4/3,5)-1-C-(acetoxymethyl)-2,3,4-tri-O-acetyl-5-azido-1,2,3,4-cyclohexanetetrol

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Chemical Property of 1L-(1,2,4/3,5)-1-C-(acetoxymethyl)-2,3,4-tri-O-acetyl-5-azido-1,2,3,4-cyclohexanetetrol

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Technology Process of 1L-(1,2,4/3,5)-1-C-(acetoxymethyl)-2,3,4-tri-O-acetyl-5-azido-1,2,3,4-cyclohexanetetrol

There total 17 articles about 1L-(1,2,4/3,5)-1-C-(acetoxymethyl)-2,3,4-tri-O-acetyl-5-azido-1,2,3,4-cyclohexanetetrol 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: 65.0%

: 108-24-7
acetic anhydride

: 693245-48-6
1L-(1,2,4/3,5)-1-C-(acetoxymethyl)-2,3,4-tri-O-acetyl-5-O-tosyl-1,2,3,4,5-cyclohexanepentol

: 694527-30-5
1L-(1,2,4/3,5)-1-C-(acetoxymethyl)-2,3,4-tri-O-acetyl-5-azido-1,2,3,4-cyclohexanetetrol

: 1L-(1,2,5/3,4)-1-C-(acetoxymethyl)-2,3,5-tri-O-acetyl-4-azido-1,2,3,5-cyclohexanetetraol

Guidance literature:: 1L-(1,2,4/3,5)-1-C-(acetoxymethyl)-2,3,4-tri-O-acetyl-5-O-tosyl-1,2,3,4,5-cyclohexanepentol; With sodium azide; In 2-methoxy-ethanol; at 120 ℃; for 21h;

acetic anhydride; With pyridine; at 20 ℃; for 1h; Further stages.;
DOI:10.1039/b314795a

Reference yield:

: C₁₁H₁₇N₃O₇

: 108-24-7
acetic anhydride

: 694527-30-5
1L-(1,2,4/3,5)-1-C-(acetoxymethyl)-2,3,4-tri-O-acetyl-5-azido-1,2,3,4-cyclohexanetetrol

Guidance literature:: With dmap; triethylamine; In tetrahydrofuran; at 0 ℃; for 1h;
DOI:10.1002/ejoc.201300804

Reference yield:

: 693245-37-3
(1S,3R,6S,8R,9S,10R)-3-phenyl-2,4-dioxabicyclo[4.4.0]decane-6,8,9,10-tetrol

: 694527-30-5
1L-(1,2,4/3,5)-1-C-(acetoxymethyl)-2,3,4-tri-O-acetyl-5-azido-1,2,3,4-cyclohexanetetrol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 41 percent / TsOH*H₂O / dimethylformamide / 4 h / 20 °C

2.1: 100 percent / pyridine; DMAP / 16 h / 20 °C

3.1: aq. HCl / 0.5 h / 60 °C

4.1: 25 mg / pyridine / 17 h / 20 °C

5.1: aq. NaN₃ / 2-methoxy-ethanol / 21 h / 120 °C

5.2: 65 percent / pyridine / 1 h / 20 °C

With pyridine; hydrogenchloride; dmap; sodium azide; toluene-4-sulfonic acid; In 2-methoxy-ethanol; N,N-dimethyl-formamide;
DOI:10.1039/b314795a