pentafluorophenyl 4-(2'-(N-acetylamino)-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)but-2-enoate

Base Information

Chemical Name:pentafluorophenyl 4-(2'-(N-acetylamino)-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)but-2-enoate
CAS No.:262286-61-3
Molecular Formula:C₃₉H₃₆F₅NO₇
Molecular Weight:725.709
Hs Code.:

Synonyms:pentafluorophenyl 4-(2'-(N-acetylamino)-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)but-2-enoate

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Chemical Property of pentafluorophenyl 4-(2'-(N-acetylamino)-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)but-2-enoate

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Technology Process of pentafluorophenyl 4-(2'-(N-acetylamino)-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)but-2-enoate

There total 6 articles about pentafluorophenyl 4-(2'-(N-acetylamino)-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)but-2-enoate 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: 92.0%

: 771-61-9
2,3,4,5,6-pentafluorophenol

: 262286-47-5
4-(2'-(N-acetylamino)-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)but-2-enoic acid

: 262286-61-3
pentafluorophenyl 4-(2'-(N-acetylamino)-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)but-2-enoate

Guidance literature:: With dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 20 ℃; for 22h;
DOI:10.1021/jo991206p

Reference yield:

: 180778-36-3
3-(2'-acetamido-3',4',6-tri-O-acetyl-2'-deoxy-α-D-glucopyranosyl)-1-propene

: 262286-61-3
pentafluorophenyl 4-(2'-(N-acetylamino)-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)but-2-enoate

Guidance literature:: Multi-step reaction with 6 steps

1: 100 percent / NaOMe / methanol / 3 h / 20 °C

2: 94 percent / NaH / dimethylformamide / 0 - 20 °C

3: 99 percent / OsO₄; NaIO₄ / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 0.25 h

4: 69 percent / tetrahydrofuran / Thermolysis

5: 86 percent / CF₃COOH / CH₂Cl₂ / 1.5 h / 20 °C

6: 92 percent / DCC / dimethylformamide / 22 h / 20 °C

With sodium periodate; osmium(VIII) oxide; sodium methylate; sodium hydride; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1: Hydrolysis / 2: Alkylation / 3: Oxidation / 4: Addition / 5: Hydrolysis / 6: Esterification;
DOI:10.1021/jo991206p

Reference yield:

: 214193-76-7
1-(2'-acetamido-2'-deoxy-α-D-glucopyranosyl)-2-propene

: 262286-61-3
pentafluorophenyl 4-(2'-(N-acetylamino)-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)but-2-enoate

Guidance literature:: Multi-step reaction with 5 steps

1: 94 percent / NaH / dimethylformamide / 0 - 20 °C

2: 99 percent / OsO₄; NaIO₄ / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 0.25 h

3: 69 percent / tetrahydrofuran / Thermolysis

4: 86 percent / CF₃COOH / CH₂Cl₂ / 1.5 h / 20 °C

5: 92 percent / DCC / dimethylformamide / 22 h / 20 °C

With sodium periodate; osmium(VIII) oxide; sodium hydride; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1: Alkylation / 2: Oxidation / 3: Addition / 4: Hydrolysis / 5: Esterification;
DOI:10.1021/jo991206p