(4R,5R)-2-phenyl-[1,3]dioxolane-4,5-dicarboxylic acid 4-{[2-(2'-N-acetylamino-4',5',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl) ethyl]-amide}-5-[(3',4'-di-O-benzyl-5'-deoxyuridin-5'-yl)-amide]

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Chemical Name:(4R,5R)-2-phenyl-[1,3]dioxolane-4,5-dicarboxylic acid 4-{[2-(2'-N-acetylamino-4',5',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl) ethyl]-amide}-5-[(3',4'-di-O-benzyl-5'-deoxyuridin-5'-yl)-amide]
CAS No.:381233-16-5
Molecular Formula:C₆₅H₆₉N₅O₁₄
Molecular Weight:1144.29
Hs Code.:

(4R,5R)-2-phenyl-[1,3]dioxolane-4,5-dicarboxylic acid 4-{[2-(2'-N-acetylamino-4',5',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl) ethyl]-amide}-5-[(3',4'-di-O-benzyl-5'-deoxyuridin-5'-yl)-amide]

Synonyms:(4R,5R)-2-phenyl-[1,3]dioxolane-4,5-dicarboxylic acid 4-{[2-(2'-N-acetylamino-4',5',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl) ethyl]-amide}-5-[(3',4'-di-O-benzyl-5'-deoxyuridin-5'-yl)-amide]

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Chemical Property of (4R,5R)-2-phenyl-[1,3]dioxolane-4,5-dicarboxylic acid 4-{[2-(2'-N-acetylamino-4',5',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl) ethyl]-amide}-5-[(3',4'-di-O-benzyl-5'-deoxyuridin-5'-yl)-amide]

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Technology Process of (4R,5R)-2-phenyl-[1,3]dioxolane-4,5-dicarboxylic acid 4-{[2-(2'-N-acetylamino-4',5',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl) ethyl]-amide}-5-[(3',4'-di-O-benzyl-5'-deoxyuridin-5'-yl)-amide]

There total 6 articles about (4R,5R)-2-phenyl-[1,3]dioxolane-4,5-dicarboxylic acid 4-{[2-(2'-N-acetylamino-4',5',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl) ethyl]-amide}-5-[(3',4'-di-O-benzyl-5'-deoxyuridin-5'-yl)-amide] 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: 79.0%

: 381233-15-4
1-amino-2-(2'-N-acetylamino-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl) ethane

: 381233-13-2
(4R,5R)-5-[(3',4'-di-O-benzyl-5'-deoxy-uridin-5'-yl)-carbamoyl]-2-phenyl-[1,3]dioxolane-4-carboxylic acid

: 381233-16-5
(4R,5R)-2-phenyl-[1,3]dioxolane-4,5-dicarboxylic acid 4-{[2-(2'-N-acetylamino-4',5',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl) ethyl]-amide}-5-[(3',4'-di-O-benzyl-5'-deoxyuridin-5'-yl)-amide]

Guidance literature:: With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; at 0 - 20 ℃; for 16h;
DOI:10.1016/S0008-6215(01)00191-4

Reference yield:

: 38270-72-3
dimethyl 2,3-O-benzylidene-L-tartrate

: 381233-16-5
(4R,5R)-2-phenyl-[1,3]dioxolane-4,5-dicarboxylic acid 4-{[2-(2'-N-acetylamino-4',5',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl) ethyl]-amide}-5-[(3',4'-di-O-benzyl-5'-deoxyuridin-5'-yl)-amide]

Guidance literature:: Multi-step reaction with 4 steps

1: 54 percent / KOH / methanol; tetrahydrofuran / 15 h / 20 °C

2: 66 percent / HOBt; DCC / tetrahydrofuran; CH₂Cl₂ / 16 h / 0 - 20 °C

3: 91 percent / LiOH*H₂O / methanol / 15 h / 20 °C

4: 79 percent / HOBt; DCC / tetrahydrofuran; CH₂Cl₂ / 16 h / 0 - 20 °C

With potassium hydroxide; lithium hydroxide; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/S0008-6215(01)00191-4

Reference yield:

: 263550-15-8
(4R,5R)-2-phenyl-[1,3]dioxolane-4,5-dicarboxylic acid monomethyl ester

: 381233-16-5
(4R,5R)-2-phenyl-[1,3]dioxolane-4,5-dicarboxylic acid 4-{[2-(2'-N-acetylamino-4',5',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl) ethyl]-amide}-5-[(3',4'-di-O-benzyl-5'-deoxyuridin-5'-yl)-amide]

Guidance literature:: Multi-step reaction with 3 steps

1: 66 percent / HOBt; DCC / tetrahydrofuran; CH₂Cl₂ / 16 h / 0 - 20 °C

2: 91 percent / LiOH*H₂O / methanol / 15 h / 20 °C

3: 79 percent / HOBt; DCC / tetrahydrofuran; CH₂Cl₂ / 16 h / 0 - 20 °C

With lithium hydroxide; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/S0008-6215(01)00191-4