2,6-anhydro-7-deoxy-7-[4-(bromomethyl)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-(bromomethyl)phenyl]-3,4,5-tri-O-acetyl-L-glycero-L-gulo-heptonic acid methyl ester
CAS No.:886226-23-9
Molecular Formula:C₂₁H₂₅BrO₉
Molecular Weight:501.328
Hs Code.:

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

There total 17 articles about 2,6-anhydro-7-deoxy-7-[4-(bromomethyl)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: 86.0%

: 886226-22-8
2,6-anhydro-7-deoxy-7-[4-(methoxymethyl)phenyl]-3,4,5-tri-O-acetyl-L-glycero-L-gulo-heptonic acid methyl ester

: 886226-23-9
2,6-anhydro-7-deoxy-7-[4-(bromomethyl)phenyl]-3,4,5-tri-O-acetyl-L-glycero-L-gulo-heptonic acid methyl ester

Guidance literature:: With hydrogen bromide; acetic acid; at 20 ℃; for 18h;
DOI:10.1016/j.bmc.2005.12.044

Reference yield: 74.0%

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

: 886226-23-9
2,6-anhydro-7-deoxy-7-[4-(bromomethyl)phenyl]-3,4,5-tri-O-acetyl-L-glycero-L-gulo-heptonic acid methyl ester

Guidance literature:: With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 2h; Inert atmosphere; Reflux;
DOI:10.1080/07328303.2016.1227831

Reference yield:

: (2R,3S,4R,5R,6S)-2-Hydroxymethyl-6-(4-methoxymethyl-benzyl)-tetrahydro-pyran-3,4,5-triol

: 886226-23-9
2,6-anhydro-7-deoxy-7-[4-(bromomethyl)phenyl]-3,4,5-tri-O-acetyl-L-glycero-L-gulo-heptonic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

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

2: dimethylformamide / 20 h / 20 °C

3: 1.90 g / pyridine; 4-(dimethylamino)pyridine / dimethylformamide / 18 h / 20 °C

4: 86 percent / HBr; acetic acid / 18 h / 20 °C

With pyridine; dmap; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; hydrogen bromide; acetic acid; potassium bromide; sodium hydrogencarbonate; In water; N,N-dimethyl-formamide;
DOI:10.1016/j.bmc.2005.12.044