C₁₅H₂₂O₉

Base Information

• Chemical Name: C₁₅H₂₂O₉
• CAS No.: 1361469-70-6
• Molecular Formula: C₁₅H₂₂O₉
• Molecular Weight: 346.334
• Mol file: 1361469-70-6.mol

Synonyms:

Chemical Property of C₁₅H₂₂O₉

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₁₅H₂₂O₉

There total 11 articles about C₁₅H₂₂O₉ 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:

(1R,2S,3R,4R)-4-[(acetyloxy)methyl]-6-oxocyclohexane-1,2,3-triyl triacetate (1027746-05-9) → C15H22O9 (1361469-70-6)

Guidance literature:

With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 20 ℃; for 1h; stereoselective reaction;

DOI:10.1002/ejoc.201100956

Reference yield:

1-chloro-1,2-dideoxy-3,4:5,7-di-O-isopropylidene-D-gluco-hept-1-enitol → C15H22O9 (1361469-70-6)

Guidance literature:

Multi-step reaction with 9 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

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

DOI:10.1002/ejoc.201100956

Reference yield:

1,2-dideoxy-3,4:5,7-bis-O-(1-methylethylidene)-D-gluco-hept-1-ynitol (117275-40-8) → C15H22O9 (1361469-70-6)

Guidance literature:

Multi-step reaction with 8 steps

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

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

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

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

5.1: pyridine / 24 h

6.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 6 h / 85 °C / Inert atmosphere

6.2: 10 h / Heating

7.1: ozone / methanol / -78 °C

7.2: -78 - 20 °C

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

With dipyridinium dichromate; 2,2'-azobis(isobutyronitrile); dimethylsulfide borane complex; tri-n-butyl-tin hydride; acetic anhydride; potassium hydride; ozone; acetic acid; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; water; toluene; mineral oil; 3.1: Peterson olefination;

DOI:10.1002/ejoc.201100956

upstream raw materials:

(1R,2S,3R,4R)-4-[(acetyloxy)methyl]-6-oxocyclohexane-1,2,3-triyl triacetate

1,2-dideoxy-3,4:5,7-bis-O-(1-methylethylidene)-D-gluco-hept-1-ynitol

(S)-4-((4R,5S)-5-Ethynyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-[1,3]dioxan-5-one

(S)-4-((4R,5S)-5-Ethynyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-5-trimethylsilanylmethyl-[1,3]dioxan-5-ol

Downstream raw materials:

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

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

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

(1R)-(+)-(1,3,5/2,4)-2,3,4,5-tetrahydroxycyclohexane-1-methanol penta-acetate