Acetic acid 2-[(2S,3S,4R,5R)-3-benzyloxy-2-benzyloxymethyl-4-(1-methoxy-1-methyl-ethoxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl]-ethyl ester

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Chemical Name:Acetic acid 2-[(2S,3S,4R,5R)-3-benzyloxy-2-benzyloxymethyl-4-(1-methoxy-1-methyl-ethoxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl]-ethyl ester
CAS No.:457068-06-3
Molecular Formula:C₄₀H₄₈N₂O₁₂S
Molecular Weight:780.893
Hs Code.:

Acetic acid 2-[(2S,3S,4R,5R)-3-benzyloxy-2-benzyloxymethyl-4-(1-methoxy-1-methyl-ethoxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl]-ethyl ester

Synonyms:Acetic acid 2-[(2S,3S,4R,5R)-3-benzyloxy-2-benzyloxymethyl-4-(1-methoxy-1-methyl-ethoxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl]-ethyl ester

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Chemical Property of Acetic acid 2-[(2S,3S,4R,5R)-3-benzyloxy-2-benzyloxymethyl-4-(1-methoxy-1-methyl-ethoxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl]-ethyl ester

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Technology Process of Acetic acid 2-[(2S,3S,4R,5R)-3-benzyloxy-2-benzyloxymethyl-4-(1-methoxy-1-methyl-ethoxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl]-ethyl ester

There total 18 articles about Acetic acid 2-[(2S,3S,4R,5R)-3-benzyloxy-2-benzyloxymethyl-4-(1-methoxy-1-methyl-ethoxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl]-ethyl 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: 90.0%

: 116-11-0
2-Methoxypropene

: 457068-05-2
3'-C-acetyloxyethyl-3',5'-di-O-benzyl-5-methyl-4'-C-(p-toluenesulfonyloxymethyl)uridine

: 457068-06-3
Acetic acid 2-[(2S,3S,4R,5R)-3-benzyloxy-2-benzyloxymethyl-4-(1-methoxy-1-methyl-ethoxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl]-ethyl ester

Guidance literature:: With toluene-4-sulfonic acid; In dichloromethane; at 0 ℃; for 3h;
DOI:10.1021/jo051187l

Reference yield:

: 197702-06-0
3-C-allyl-3-O-benzyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

: 457068-06-3
Acetic acid 2-[(2S,3S,4R,5R)-3-benzyloxy-2-benzyloxymethyl-4-(1-methoxy-1-methyl-ethoxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl]-ethyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: aqueous acetic acid / 3 h / 40 °C

2: sodium periodate / tetrahydrofuran; H₂O / 0.75 h / 0 °C

3: 2.9 g / sodium hydroxide / tetrahydrofuran; H₂O / 18 h / 20 °C

4: 65 percent / sodium hydride / dimethylformamide / 1.5 h / 20 °C

5: 93 percent / Et₃N; DMAP / CH₂Cl₂ / 19 h / 20 °C

6: NaIO₄; H₂O / OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 2 h / 20 °C

7: 754 mg / sodium tetrahydroborate / tetrahydrofuran; H₂O / 1 h / 0 °C

8: 98 percent / H₂SO₄; acetic acid / 6 h / 20 °C

9: 95 percent / N,O-bis(trimethylsilyl)acetamide; TMSOTf / 1,2-dichloro-ethane / 9 h / Heating

10: 87 percent / MeNH₂ / tetrahydrofuran; H₂O / 2 h / 0 °C

11: 90 percent / p-TsOH*H₂O / CH₂Cl₂ / 3 h / 0 °C

With dmap; sodium hydroxide; sodium tetrahydroborate; sodium periodate; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; water; sodium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; methylamine; osmium(VIII) oxide; In tetrahydrofuran; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; tert-butyl alcohol; 3: aldol-Cannizzaro reaction;
DOI:10.1021/jo051187l

Reference yield:

: 457067-99-1
3-C-allyl-3-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose

: 457068-06-3
Acetic acid 2-[(2S,3S,4R,5R)-3-benzyloxy-2-benzyloxymethyl-4-(1-methoxy-1-methyl-ethoxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl]-ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 65 percent / sodium hydride / dimethylformamide / 1.5 h / 20 °C

2: 93 percent / Et₃N; DMAP / CH₂Cl₂ / 19 h / 20 °C

3: NaIO₄; H₂O / OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 2 h / 20 °C

4: 754 mg / sodium tetrahydroborate / tetrahydrofuran; H₂O / 1 h / 0 °C

5: 98 percent / H₂SO₄; acetic acid / 6 h / 20 °C

6: 95 percent / N,O-bis(trimethylsilyl)acetamide; TMSOTf / 1,2-dichloro-ethane / 9 h / Heating

7: 87 percent / MeNH₂ / tetrahydrofuran; H₂O / 2 h / 0 °C

8: 90 percent / p-TsOH*H₂O / CH₂Cl₂ / 3 h / 0 °C

With dmap; sodium tetrahydroborate; sodium periodate; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; water; sodium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; methylamine; osmium(VIII) oxide; In tetrahydrofuran; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/jo051187l