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

Base Information

Chemical Name:4-(2'-(N-acetylamino)-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)but-2-enoic acid
CAS No.:262286-47-5
Molecular Formula:C₃₃H₃₇NO₇
Molecular Weight:559.659
Hs Code.:

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

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

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

There total 5 articles about 4-(2'-(N-acetylamino)-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)but-2-enoic acid 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%

: 262286-57-7
tert-butyl 4-(2'-(N-acetylamino)-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)but-2-enoate

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

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1.5h;
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

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

Guidance literature:: Multi-step reaction with 5 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

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

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 4 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

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