(1S,2S,3R,4R,6S)-4-(acetoxymethyl)-6-azidocyclohexane-1,2,3-triyl triacetate

Base Information

• Chemical Name: (1S,2S,3R,4R,6S)-4-(acetoxymethyl)-6-azidocyclohexane-1,2,3-triyl triacetate
• CAS No.: 97747-53-0
• Molecular Formula: C₁₅H₂₁N₃O₈
• Molecular Weight: 371.347
• Mol file: 97747-53-0.mol

Synonyms:(1S,2S,3R,4R,6S)-4-(acetoxymethyl)-6-azidocyclohexane-1,2,3-triyl triacetate

Chemical Property of (1S,2S,3R,4R,6S)-4-(acetoxymethyl)-6-azidocyclohexane-1,2,3-triyl triacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,3R,4R,6S)-4-(acetoxymethyl)-6-azidocyclohexane-1,2,3-triyl triacetate

There total 20 articles about (1S,2S,3R,4R,6S)-4-(acetoxymethyl)-6-azidocyclohexane-1,2,3-triyl triacetate 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: 89.0%

(1R)-(-)-(1,3,5/2,4)-2,3,4-triacetoxy-1-acetoxymethyl-5-bromocyclohexane (97747-52-9) → (1S,2S,3R,4R,6S)-4-(acetoxymethyl)-6-azidocyclohexane-1,2,3-triyl triacetate (97747-53-0)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide;

DOI:10.1039/P19850000903

Reference yield:

C16H24O11S → (1S,2S,3R,4R,6S)-4-(acetoxymethyl)-6-azidocyclohexane-1,2,3-triyl triacetate (97747-53-0)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 85 ℃; for 48h;

DOI:10.1002/ejoc.201100956

Reference yield:

1-chloro-1,2-dideoxy-3,4:5,7-di-O-isopropylidene-D-gluco-hept-1-enitol → (1S,2S,3R,4R,6S)-4-(acetoxymethyl)-6-azidocyclohexane-1,2,3-triyl triacetate (97747-53-0)

Guidance literature:

Multi-step reaction with 11 steps

1.1: n-butyllithium / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere

2.1: dipyridinium dichromate; acetic anhydride / dichloromethane / 16 h / 20 °C

3.1: diethyl ether / 6 h / 0 - 20 °C / Inert atmosphere

4.1: potassium hydride / tetrahydrofuran; mineral oil / 0.33 h / 0 °C / Inert atmosphere

5.1: acetic acid / tetrahydrofuran; water / 5 h / Heating

6.1: pyridine / 24 h

7.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 6 h / 85 °C / Inert atmosphere

7.2: 10 h / Heating

8.1: ozone / methanol / -78 °C

8.2: -78 - 20 °C

9.1: dimethylsulfide borane complex / tetrahydrofuran / 1 h / 0 - 20 °C

10.1: triethylamine / dichloromethane / 0.5 h / 0 - 20 °C

11.1: sodium azide / N,N-dimethyl-formamide / 48 h / 85 °C

With dipyridinium dichromate; n-butyllithium; sodium azide; 2,2'-azobis(isobutyronitrile); dimethylsulfide borane complex; tri-n-butyl-tin hydride; acetic anhydride; potassium hydride; ozone; acetic acid; triethylamine; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; mineral oil; 4.1: Peterson olefination;

DOI:10.1002/ejoc.201100956

upstream raw materials:

(1R)-(-)-(1,3,5/2,4)-2,3,4-triacetoxy-1-acetoxymethyl-5-bromocyclohexane

(-)-7-endo-oxabicyclo<2.2.1>hept-5-ene-2-carboxylic acid

(1R)-(-)-1,2,3-tri-O-acetyl-(1,3/2,4,6)-4-bromo-6-bromomethyl-1,2,3-cyclohexanetriol

(3R)-(+)-2-exo-hydroxy-4,8-dioxatricyclo<4.2.1.0^3,7>nonan-5-one

Downstream raw materials:

(1R,2R,3S,6R)-6-(acetoxymethyl)cyclohex-4-ene-1,2,3-triyl triacetate

1-deoxy-2,3,4,6-tetra-O-acetyl-5a-carba-D-glucopyranose

(1S,2S,3R,4R,6S)-4-(acetoxymethyl)-6-(4-phenyl-1H-1,2,3-triazol-1-yl)cyclohexane-1,2,3-triyl triacetate

(1S,2S,3R,4R,6S)-4-(acetoxymethyl)-6-[4-(4-methylphenyl)-1H-1,2,3-triazol-1-yl]cyclohexane-1,2,3-triyl triacetate