4-((2R,3S,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-N-[(2R,3R,4R,5R)-3,4-bis-benzyloxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-2,3-dihydroxy-butyramide

Base Information

Chemical Name:4-((2R,3S,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-N-[(2R,3R,4R,5R)-3,4-bis-benzyloxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-2,3-dihydroxy-butyramide
CAS No.:262286-55-5
Molecular Formula:C₅₆H₆₂N₄O₁₃
Molecular Weight:999.127
Hs Code.:

4-((2R,3S,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-N-[(2R,3R,4R,5R)-3,4-bis-benzyloxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-2,3-dihydroxy-butyramide

Synonyms:4-((2R,3S,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-N-[(2R,3R,4R,5R)-3,4-bis-benzyloxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-2,3-dihydroxy-butyramide

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Chemical Property of 4-((2R,3S,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-N-[(2R,3R,4R,5R)-3,4-bis-benzyloxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-2,3-dihydroxy-butyramide

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Technology Process of 4-((2R,3S,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-N-[(2R,3R,4R,5R)-3,4-bis-benzyloxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-2,3-dihydroxy-butyramide

There total 11 articles about 4-((2R,3S,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-N-[(2R,3R,4R,5R)-3,4-bis-benzyloxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-2,3-dihydroxy-butyramide 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: 84.0%

: 262286-54-4
(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]-amide

: 262286-55-5
4-((2R,3S,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-N-[(2R,3R,4R,5R)-3,4-bis-benzyloxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-2,3-dihydroxy-butyramide

Guidance literature:: With osmium(VIII) oxide; N-methyl-2-indolinone; In tetrahydrofuran; water; tert-butyl alcohol; at 20 ℃; for 72h;
DOI:10.1021/jo991206p

Reference yield:

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

: 262286-55-5
4-((2R,3S,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-N-[(2R,3R,4R,5R)-3,4-bis-benzyloxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-2,3-dihydroxy-butyramide

Guidance literature:: Multi-step reaction with 4 steps

1: 95 percent / PPh₃; CBr₄; NaN₃ / dimethylformamide / 15 h / 90 °C

2: 60 percent / NaBH₄; HS(CH₂)3SH; Et₃N / propan-2-ol / 2 h / 70 °C

3: 94 percent / DMAP / dimethylformamide / 48 h / 20 °C

4: 84 percent / OsO₄; NMO / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 72 h / 20 °C

With 1.3-propanedithiol; dmap; sodium tetrahydroborate; osmium(VIII) oxide; sodium azide; N-methyl-2-indolinone; carbon tetrabromide; triethylamine; triphenylphosphine; In tetrahydrofuran; water; N,N-dimethyl-formamide; isopropyl alcohol; tert-butyl alcohol; 1: Substitution / 2: Reduction / 3: Acylation / 4: Oxidation;
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

: 262286-55-5
4-((2R,3S,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-N-[(2R,3R,4R,5R)-3,4-bis-benzyloxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-2,3-dihydroxy-butyramide

Guidance literature:: Multi-step reaction with 8 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

7: 94 percent / DMAP / dimethylformamide / 48 h / 20 °C

8: 84 percent / OsO₄; NMO / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 72 h / 20 °C

With dmap; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; 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 / 7: Acylation / 8: Oxidation;
DOI:10.1021/jo991206p