2,6-anhydro-7-deoxy-7-[4-(retinoylmethyl)phenyl]-3,4,5-tri-O-acetyl-L-glycero-L-gulo-heptonic acid methyl ester

Base Information

• Chemical Name: 2,6-anhydro-7-deoxy-7-[4-(retinoylmethyl)phenyl]-3,4,5-tri-O-acetyl-L-glycero-L-gulo-heptonic acid methyl ester
• CAS No.: 886226-26-2
• Molecular Formula: C₄₁H₅₂O₁₀
• Molecular Weight: 704.858
• Mol file: 886226-26-2.mol

Synonyms:2,6-anhydro-7-deoxy-7-[4-(retinoylmethyl)phenyl]-3,4,5-tri-O-acetyl-L-glycero-L-gulo-heptonic acid methyl ester

Chemical Property of 2,6-anhydro-7-deoxy-7-[4-(retinoylmethyl)phenyl]-3,4,5-tri-O-acetyl-L-glycero-L-gulo-heptonic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,6-anhydro-7-deoxy-7-[4-(retinoylmethyl)phenyl]-3,4,5-tri-O-acetyl-L-glycero-L-gulo-heptonic acid methyl ester

There total 13 articles about 2,6-anhydro-7-deoxy-7-[4-(retinoylmethyl)phenyl]-3,4,5-tri-O-acetyl-L-glycero-L-gulo-heptonic acid methyl ester 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: 75.0%

(2S,3S,4R,5S,6S)-3,4,5-Triacetoxy-6-{4-[(3E,5E,7E,9E)-2-(tert-butyl-dimethyl-silanyloxy)-2-cyano-4,8-dimethyl-10-(2,6,6-trimethyl-cyclohex-1-enyl)-deca-3,5,7,9-tetraenyl]-benzyl}-tetrahydro-pyran-2-carboxylic acid methyl ester (886226-25-1) → 2,6-anhydro-7-deoxy-7-[4-(retinoylmethyl)phenyl]-3,4,5-tri-O-acetyl-L-glycero-L-gulo-heptonic acid methyl ester (886226-26-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; water; for 1h;

DOI:10.1016/j.bmc.2005.12.044

Reference yield:

(2R,3S,4R,5R,6S)-2-Hydroxymethyl-6-(4-methoxymethyl-benzyl)-tetrahydro-pyran-3,4,5-triol → 2,6-anhydro-7-deoxy-7-[4-(retinoylmethyl)phenyl]-3,4,5-tri-O-acetyl-L-glycero-L-gulo-heptonic acid methyl ester (886226-26-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 2,2,6,6-tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite; KBr / NaHCO₃ / H₂O / 0.75 h / 0 °C

2.1: dimethylformamide / 20 h / 20 °C

3.1: 1.90 g / pyridine; 4-(dimethylamino)pyridine / dimethylformamide / 18 h / 20 °C

4.1: 86 percent / HBr; acetic acid / 18 h / 20 °C

5.1: hexamethyldisilazane lithium salt / tetrahydrofuran; hexane / 0.5 h / -78 °C

5.2: 47 percent / tetrahydrofuran; hexane / 3 h / -78 °C

6.1: 75 percent / tetrabutylammonium fluoride / tetrahydrofuran; H₂O / 1 h

With pyridine; dmap; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutyl ammonium fluoride; hydrogen bromide; acetic acid; potassium bromide; lithium hexamethyldisilazane; sodium hydrogencarbonate; In tetrahydrofuran; hexane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2005.12.044

Reference yield:

2,6-anhydro-1-deoxy-1-[4-(hydroxymethyl)phenyl]-3,4,5,7-tetra-O-(methoxymethyl)-D-glycero-D-gulo-heptitol (886226-20-6) → 2,6-anhydro-7-deoxy-7-[4-(retinoylmethyl)phenyl]-3,4,5-tri-O-acetyl-L-glycero-L-gulo-heptonic acid methyl ester (886226-26-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 94 percent / sodium hydride / tetrahydrofuran / 18 h

2.1: HCl / methanol; H₂O / 18 h / 20 °C

3.1: 2,2,6,6-tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite; KBr / NaHCO₃ / H₂O / 0.75 h / 0 °C

4.1: dimethylformamide / 20 h / 20 °C

5.1: 1.90 g / pyridine; 4-(dimethylamino)pyridine / dimethylformamide / 18 h / 20 °C

6.1: 86 percent / HBr; acetic acid / 18 h / 20 °C

7.1: hexamethyldisilazane lithium salt / tetrahydrofuran; hexane / 0.5 h / -78 °C

7.2: 47 percent / tetrahydrofuran; hexane / 3 h / -78 °C

8.1: 75 percent / tetrabutylammonium fluoride / tetrahydrofuran; H₂O / 1 h

With pyridine; hydrogenchloride; dmap; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutyl ammonium fluoride; hydrogen bromide; sodium hydride; acetic acid; potassium bromide; lithium hexamethyldisilazane; sodium hydrogencarbonate; In tetrahydrofuran; methanol; hexane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2005.12.044

upstream raw materials:

(2S,3S,4R,5S,6S)-3,4,5-Triacetoxy-6-{4-[(3E,5E,7E,9E)-2-(tert-butyl-dimethyl-silanyloxy)-2-cyano-4,8-dimethyl-10-(2,6,6-trimethyl-cyclohex-1-enyl)-deca-3,5,7,9-tetraenyl]-benzyl}-tetrahydro-pyran-2-carboxylic acid methyl ester

2,6-anhydro-7-deoxy-7-[4-(bromomethyl)phenyl]-3,4,5-tri-O-acetyl-L-glycero-L-gulo-heptonic acid methyl ester

2,6-anhydro-7-deoxy-7-[4-(methoxymethyl)phenyl]-3,4,5-tri-O-acetyl-L-glycero-L-gulo-heptonic acid methyl ester

2,6-anhydro-1-deoxy-1-[4-(hydroxymethyl)phenyl]-3,4,5,7-tetra-O-(methoxymethyl)-D-glycero-D-gulo-heptitol

Refernces

• 1、 -. "C-linked glucuronide of N-(4-hydroxybenzyl) retinone, analogs thereof, and method of using the same to inhibit neoplastic cell growth". Page/Page column 5; 11. . Retrieved 2008/06/13.