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
Hs Code.:

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

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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

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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%

: 886226-25-1
(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

: 886226-26-2
2,6-anhydro-7-deoxy-7-[4-(retinoylmethyl)phenyl]-3,4,5-tri-O-acetyl-L-glycero-L-gulo-heptonic acid methyl ester

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

: 886226-26-2
2,6-anhydro-7-deoxy-7-[4-(retinoylmethyl)phenyl]-3,4,5-tri-O-acetyl-L-glycero-L-gulo-heptonic acid methyl ester

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:

: 886226-20-6
2,6-anhydro-1-deoxy-1-[4-(hydroxymethyl)phenyl]-3,4,5,7-tetra-O-(methoxymethyl)-D-glycero-D-gulo-heptitol

: 886226-26-2
2,6-anhydro-7-deoxy-7-[4-(retinoylmethyl)phenyl]-3,4,5-tri-O-acetyl-L-glycero-L-gulo-heptonic acid methyl ester

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