(3R,3'R)-alloxanthin acetate

Base Information

• Chemical Name: (3R,3'R)-alloxanthin acetate
• CAS No.: 95404-19-6
• Molecular Formula: C₄₄H₅₆O₄
• Molecular Weight: 648.926
• Mol file: 95404-19-6.mol

Synonyms:

Chemical Property of (3R,3'R)-alloxanthin acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,3'R)-alloxanthin acetate

There total 19 articles about (3R,3'R)-alloxanthin acetate 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:

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7) + (R,E)-4-[5-(diethoxyphosphoryl)-3-methylpent-3-en-1-ynyl]-3,5,5-trimethylcyclohex-3-enyl acetate → (3R,3'R)-alloxanthin acetate (11048-74-1,25494-87-5,95404-19-6)

Guidance literature:

(R,E)-4-[5-(diethoxyphosphoryl)-3-methylpent-3-en-1-ynyl]-3,5,5-trimethylcyclohex-3-enyl acetate; With sodium hexamethyldisilazane; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial; In tetrahydrofuran; hexane; at -78 ℃; for 2h; Inert atmosphere;

DOI:10.1039/c4ob02144d

Reference yield:

2-cis-5-(4',4'-ethylenedioxy-1'-hydroxy-2',2',6'-trimethylcyclohexyl)-3-methylpent-2-en-4-yn-1-ol (95307-31-6,95343-60-5,137432-90-7) → 9-cis-9'-cis-3,3'-diacetoxy-7,8,7',8'-tetradehydro-β,β-carotene (11048-74-1,25494-87-5,95404-19-6)

Guidance literature:

Multi-step reaction with 7 steps

1: aq. acetic acid / Heating

2: LiAlH₄ / diethyl ether / 20 °C

3: 2.9 g / methanol / 60 h / 20 °C

4: 314 mg / 1.) NaOMe / 1.) MeOH, 15 min, 2.) reflux, 1 h

5: 25 mg / 1.) NaOMe / 1.) MeOH, 15 min, 2.) reflux

6: 18 mg / pyridine / 14 h

7: 4 mg / POCl₃ / pyridine / 12 h

With lithium aluminium tetrahydride; sodium methylate; trichlorophosphate; In pyridine; methanol; diethyl ether; acetic acid;

Reference yield:

(R)-4-ethynyl-3,5,5-trimethylcyclohex-3-enyl acetate (76530-42-2,118829-54-2) → (3R,3'R)-alloxanthin acetate (11048-74-1,25494-87-5,95404-19-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 4 h / 25 °C / Inert atmosphere

2.1: sodium hexamethyldisilazane / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

2.2: 2 h / -78 °C / Inert atmosphere

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hexamethyldisilazane; triethylamine; In tetrahydrofuran; hexane;

DOI:10.1039/c4ob02144d

upstream raw materials:

Acetic acid (1R,4S,5R)-4-[(3Z,5E,7E,9E,11E,13E,15Z)-18-((1S,4R,6R)-4-acetoxy-1-hydroxy-2,2,6-trimethyl-cyclohexyl)-3,7,12,16-tetramethyl-octadeca-3,5,7,9,11,13,15-heptaene-1,17-diynyl]-4-hydroxy-3,3,5-trimethyl-cyclohexyl ester

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial

2-cis-5-(4',4'-ethylenedioxy-1'-hydroxy-2',2',6'-trimethylcyclohexyl)-3-methylpent-2-en-4-yn-1-ol

2-cis-5-(1'-hydroxy-2',2',6'-trimethyl-4'-oxocyclohexyl)-3-methylpent-2-en-4-yn-1-ol

Downstream raw materials:

(3R',3'R)-alloxanthin