Benzyl 2-Acetamido-4-O-acetyl-2-deoxy-3-O-<(R)-1-(ethoxycarbonyl)ethyl>-α-D-glucopyranosiduronic Acid Benzyl Ester

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Chemical Name:Benzyl 2-Acetamido-4-O-acetyl-2-deoxy-3-O-<(R)-1-(ethoxycarbonyl)ethyl>-α-D-glucopyranosiduronic Acid Benzyl Ester
CAS No.:129392-11-6
Molecular Formula:C₂₈H₃₃NO₁₀
Molecular Weight:543.571
Hs Code.:

Synonyms:Benzyl 2-Acetamido-4-O-acetyl-2-deoxy-3-O-<(R)-1-(ethoxycarbonyl)ethyl>-α-D-glucopyranosiduronic Acid Benzyl Ester

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Chemical Property of Benzyl 2-Acetamido-4-O-acetyl-2-deoxy-3-O-<(R)-1-(ethoxycarbonyl)ethyl>-α-D-glucopyranosiduronic Acid Benzyl Ester

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Technology Process of Benzyl 2-Acetamido-4-O-acetyl-2-deoxy-3-O-<(R)-1-(ethoxycarbonyl)ethyl>-α-D-glucopyranosiduronic Acid Benzyl Ester

There total 10 articles about Benzyl 2-Acetamido-4-O-acetyl-2-deoxy-3-O-<(R)-1-(ethoxycarbonyl)ethyl>-α-D-glucopyranosiduronic Acid Benzyl 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: 62.0%

: 108-24-7
acetic anhydride

: 129392-10-5
Benzyl 2-Acetamido-2-deoxy-3-O-<(R)-1-(methoxycarbonyl))ethyl>-α-D-glucopyranosiduronic Acid Benzyl ester

: 129392-11-6
Benzyl 2-Acetamido-4-O-acetyl-2-deoxy-3-O-<(R)-1-(ethoxycarbonyl)ethyl>-α-D-glucopyranosiduronic Acid Benzyl Ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; for 1h; Ambient temperature;
DOI:10.1021/jo00311a026

Reference yield:

: 10036-64-3
N-acetyl-D-glucosamine

: 129392-11-6
Benzyl 2-Acetamido-4-O-acetyl-2-deoxy-3-O-<(R)-1-(ethoxycarbonyl)ethyl>-α-D-glucopyranosiduronic Acid Benzyl Ester

Guidance literature:: Multi-step reaction with 9 steps

1: HCl gas / 0.33 h / 95 °C

2: p-toluenesulfonic acid monohydrate / acetone / 2 h / Ambient temperature

3: 1) NaH / 1) THF, 2) 50 deg C, 18 h

4: acetic acid / ethanol; H₂O / 2 h / Heating

5: p-toluenesulfonic acid monohydrate / acetonitrile / 3 h / Heating

6: 68 percent / NaIO₄, RuCl₃*H₂O / acetonitrile; CCl₄; H₂O / 0.67 h / Ambient temperature

7: 90 percent / 18 h / Heating

8: 89 percent / NaHCO₃ / dimethylformamide / 16 h / 60 °C

9: 62 percent / triethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h / Ambient temperature

With hydrogenchloride; dmap; ruthenium trichloride; sodium periodate; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; In tetrachloromethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1021/jo00311a026

Reference yield:

: 66026-10-6
N-((4aR,6S,7R,8R,8aS)-6-(benzyloxy)-8-hydroxy-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-7-yl)acetamide

: 129392-11-6
Benzyl 2-Acetamido-4-O-acetyl-2-deoxy-3-O-<(R)-1-(ethoxycarbonyl)ethyl>-α-D-glucopyranosiduronic Acid Benzyl Ester

Guidance literature:: Multi-step reaction with 7 steps

1: 1) NaH / 1) THF, 2) 50 deg C, 18 h

2: acetic acid / ethanol; H₂O / 2 h / Heating

3: p-toluenesulfonic acid monohydrate / acetonitrile / 3 h / Heating

4: 68 percent / NaIO₄, RuCl₃*H₂O / acetonitrile; CCl₄; H₂O / 0.67 h / Ambient temperature

5: 90 percent / 18 h / Heating

6: 89 percent / NaHCO₃ / dimethylformamide / 16 h / 60 °C

7: 62 percent / triethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h / Ambient temperature

With dmap; ruthenium trichloride; sodium periodate; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; In tetrachloromethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo00311a026