1-(4-C-acetoxymethyl-3-C-allyl-3-O-benzyl-2,5-di-O-acetyl-β-D-erythro-pentofuranosyl)thymine

Base Information

Chemical Name:1-(4-C-acetoxymethyl-3-C-allyl-3-O-benzyl-2,5-di-O-acetyl-β-D-erythro-pentofuranosyl)thymine
CAS No.:485755-32-6
Molecular Formula:C₂₇H₃₂N₂O₁₀
Molecular Weight:544.558
Hs Code.:

Synonyms:1-(4-C-acetoxymethyl-3-C-allyl-3-O-benzyl-2,5-di-O-acetyl-β-D-erythro-pentofuranosyl)thymine

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Chemical Property of 1-(4-C-acetoxymethyl-3-C-allyl-3-O-benzyl-2,5-di-O-acetyl-β-D-erythro-pentofuranosyl)thymine

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Technology Process of 1-(4-C-acetoxymethyl-3-C-allyl-3-O-benzyl-2,5-di-O-acetyl-β-D-erythro-pentofuranosyl)thymine

There total 5 articles about 1-(4-C-acetoxymethyl-3-C-allyl-3-O-benzyl-2,5-di-O-acetyl-β-D-erythro-pentofuranosyl)thymine 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: 67.0%

: 65-71-4,28806-14-6,691841-57-3
thymin

: 485755-31-5
4-C-acetoxymethyl-3-C-allyl-3-O-benzyl-1,2,5-tri-O-acetyl-D-erythro-pentofuranose

: 485755-32-6
1-(4-C-acetoxymethyl-3-C-allyl-3-O-benzyl-2,5-di-O-acetyl-β-D-erythro-pentofuranosyl)thymine

Guidance literature:: With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 60 ℃;
DOI:10.1039/b205031e

Reference yield:

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

: 485755-32-6
1-(4-C-acetoxymethyl-3-C-allyl-3-O-benzyl-2,5-di-O-acetyl-β-D-erythro-pentofuranosyl)thymine

Guidance literature:: Multi-step reaction with 6 steps

1.1: aq. acetic acid / methanol / 18 h

2.1: NaIO₄ / tetrahydrofuran; H₂O / 1 h / 20 °C

2.2: aq. NaOH / tetrahydrofuran; methanol / 12 h / 20 °C

2.3: 3.69 g / NaBH₄ / tetrahydrofuran; methanol / 1 h / 20 °C

3.1: 85 percent / pyridine; DMAP / 12 h / 20 °C

4.1: aq. acetic acid / 3 h / 90 °C

5.1: 3.38 g / pyridine; DMAP / 12 h / 20 °C

6.1: 63 percent / N,O-(bistrimethyl)acetamide; trimethylsilyl triflate / acetonitrile / 3 h / Heating

With pyridine; dmap; sodium periodate; trimethylsilyl trifluoromethanesulfonate; N,O-(bistrimethyl)acetamide; acetic acid; In tetrahydrofuran; methanol; water; acetonitrile;
DOI:10.1021/jo049159a

Reference yield:

: 100-39-0
benzyl bromide

: 485755-32-6
1-(4-C-acetoxymethyl-3-C-allyl-3-O-benzyl-2,5-di-O-acetyl-β-D-erythro-pentofuranosyl)thymine

Guidance literature:: Multi-step reaction with 7 steps

1.1: 95 percent / NaH / dimethylformamide / 3 h / 20 °C

2.1: aq. acetic acid / methanol / 18 h

3.1: NaIO₄ / tetrahydrofuran; H₂O / 1 h / 20 °C

3.2: aq. NaOH / tetrahydrofuran; methanol / 12 h / 20 °C

3.3: 3.69 g / NaBH₄ / tetrahydrofuran; methanol / 1 h / 20 °C

4.1: 85 percent / pyridine; DMAP / 12 h / 20 °C

5.1: aq. acetic acid / 3 h / 90 °C

6.1: 3.38 g / pyridine; DMAP / 12 h / 20 °C

7.1: 63 percent / N,O-(bistrimethyl)acetamide; trimethylsilyl triflate / acetonitrile / 3 h / Heating

With pyridine; dmap; sodium periodate; trimethylsilyl trifluoromethanesulfonate; N,O-(bistrimethyl)acetamide; sodium hydride; acetic acid; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo049159a