2,6-anhydro-7-deoxy-7-[4-(methoxymethyl)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-(methoxymethyl)phenyl]-3,4,5-tri-O-acetyl-L-glycero-L-gulo-heptonic acid methyl ester
CAS No.:886226-22-8
Molecular Formula:C₂₂H₂₈O₁₀
Molecular Weight:452.458
Hs Code.:

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

There total 11 articles about 2,6-anhydro-7-deoxy-7-[4-(methoxymethyl)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:

: (2S,3S,4R,5R,6S)-3,4,5-Trihydroxy-6-(4-methoxymethyl-benzyl)-tetrahydro-pyran-2-carboxylic acid

: 108-24-7
acetic anhydride

: 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

Guidance literature:: (2S,3S,4R,5R,6S)-3,4,5-Trihydroxy-6-(4-methoxymethyl-benzyl)-tetrahydro-pyran-2-carboxylic acid; methyl iodide; In N,N-dimethyl-formamide; at 20 ℃; for 20h;

acetic anhydride; With pyridine; dmap; In N,N-dimethyl-formamide; for 18h;

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 3 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

With pyridine; dmap; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide; sodium hydrogencarbonate; In 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

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

Guidance literature:: Multi-step reaction with 5 steps

1: 94 percent / sodium hydride / tetrahydrofuran / 18 h

2: HCl / methanol; H₂O / 18 h / 20 °C

3: 2,2,6,6-tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite; KBr / NaHCO₃ / H₂O / 0.75 h / 0 °C

4: dimethylformamide / 20 h / 20 °C

5: 1.90 g / pyridine; 4-(dimethylamino)pyridine / dimethylformamide / 18 h / 20 °C

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