(E)-4-((2R,3S,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-but-2-enoic acid (2R,3R,4R,5R)-3,4-bis-benzyloxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

Base Information

Chemical Name:(E)-4-((2R,3S,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-but-2-enoic acid (2R,3R,4R,5R)-3,4-bis-benzyloxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester
CAS No.:262286-52-2
Molecular Formula:C₅₆H₅₉N₃O₁₂
Molecular Weight:966.097
Hs Code.:

(E)-4-((2R,3S,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-but-2-enoic acid (2R,3R,4R,5R)-3,4-bis-benzyloxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

Synonyms:(E)-4-((2R,3S,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-but-2-enoic acid (2R,3R,4R,5R)-3,4-bis-benzyloxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

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Chemical Property of (E)-4-((2R,3S,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-but-2-enoic acid (2R,3R,4R,5R)-3,4-bis-benzyloxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

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Technology Process of (E)-4-((2R,3S,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-but-2-enoic acid (2R,3R,4R,5R)-3,4-bis-benzyloxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

There total 6 articles about (E)-4-((2R,3S,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-but-2-enoic acid (2R,3R,4R,5R)-3,4-bis-benzyloxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl 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: 58.0%

: 40733-60-6
2',3'-di-O-benzoyluridine

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

: 262286-52-2
(E)-4-((2R,3S,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-but-2-enoic acid (2R,3R,4R,5R)-3,4-bis-benzyloxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

Guidance literature:: 4-(2'-(N-acetylamino)-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)but-2-enoic acid; With chloroformic acid ethyl ester; triethylamine; In dichloromethane; at -10 ℃; for 0.333333h;

2',3'-di-O-benzoyluridine; With dmap; In dichloromethane; at 20 ℃; for 48h; Further stages.;
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

: 262286-52-2
(E)-4-((2R,3S,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-but-2-enoic acid (2R,3R,4R,5R)-3,4-bis-benzyloxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 100 percent / NaOMe / methanol / 3 h / 20 °C

2.1: 94 percent / NaH / dimethylformamide / 0 - 20 °C

3.1: 99 percent / OsO₄; NaIO₄ / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 0.25 h

4.1: 69 percent / tetrahydrofuran / Thermolysis

5.1: 86 percent / CF₃COOH / CH₂Cl₂ / 1.5 h / 20 °C

6.1: EtOCOCl; Et₃N / CH₂Cl₂ / 0.33 h / -10 °C

6.2: 58 percent / DMAP / CH₂Cl₂ / 48 h / 20 °C

With sodium periodate; osmium(VIII) oxide; sodium methylate; chloroformic acid ethyl ester; sodium hydride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Hydrolysis / 2.1: Alkylation / 3.1: Oxidation / 4.1: Addition / 5.1: Hydrolysis / 6.1: Acylation / 6.2: Acylation;
DOI:10.1021/jo991206p

Reference yield:

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

: 262286-52-2
(E)-4-((2R,3S,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-but-2-enoic acid (2R,3R,4R,5R)-3,4-bis-benzyloxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 94 percent / NaH / dimethylformamide / 0 - 20 °C

2.1: 99 percent / OsO₄; NaIO₄ / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 0.25 h

3.1: 69 percent / tetrahydrofuran / Thermolysis

4.1: 86 percent / CF₃COOH / CH₂Cl₂ / 1.5 h / 20 °C

5.1: EtOCOCl; Et₃N / CH₂Cl₂ / 0.33 h / -10 °C

5.2: 58 percent / DMAP / CH₂Cl₂ / 48 h / 20 °C

With sodium periodate; osmium(VIII) oxide; chloroformic acid ethyl ester; sodium hydride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Alkylation / 2.1: Oxidation / 3.1: Addition / 4.1: Hydrolysis / 5.1: Acylation / 5.2: Acylation;
DOI:10.1021/jo991206p