1-(2-O-acetyl-3-C-allyl-3,5-di-O-benzyl-4-C-(1(S)-(benzoyloxy)allyl)-β-D-ribofuranosyl)thymine

Base Information

Chemical Name:1-(2-O-acetyl-3-C-allyl-3,5-di-O-benzyl-4-C-(1(S)-(benzoyloxy)allyl)-β-D-ribofuranosyl)thymine
CAS No.:485755-41-7
Molecular Formula:C₃₉H₄₀N₂O₉
Molecular Weight:680.755
Hs Code.:

Synonyms:1-(2-O-acetyl-3-C-allyl-3,5-di-O-benzyl-4-C-(1(S)-(benzoyloxy)allyl)-β-D-ribofuranosyl)thymine

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Chemical Property of 1-(2-O-acetyl-3-C-allyl-3,5-di-O-benzyl-4-C-(1(S)-(benzoyloxy)allyl)-β-D-ribofuranosyl)thymine

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Technology Process of 1-(2-O-acetyl-3-C-allyl-3,5-di-O-benzyl-4-C-(1(S)-(benzoyloxy)allyl)-β-D-ribofuranosyl)thymine

There total 7 articles about 1-(2-O-acetyl-3-C-allyl-3,5-di-O-benzyl-4-C-(1(S)-(benzoyloxy)allyl)-β-D-ribofuranosyl)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: 93.0%

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

: 485755-40-6
1,2-di-O-acetyl-3-C-allyl-3,5-di-O-benzyl-4-C-(1(S)-(benzoyloxy)allyl)-α/β-D-ribofuranose

: 485755-41-7
1-(2-O-acetyl-3-C-allyl-3,5-di-O-benzyl-4-C-(1(S)-(benzoyloxy)allyl)-β-D-ribofuranosyl)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

: 485755-41-7
1-(2-O-acetyl-3-C-allyl-3,5-di-O-benzyl-4-C-(1(S)-(benzoyloxy)allyl)-β-D-ribofuranosyl)thymine

Guidance literature:: Multi-step reaction with 8 steps

1.1: H₅IO₆ / ethyl acetate

1.2: aq. NaOH / tetrahydrofuran

1.3: 82 percent / NaBH₄

2.1: 55 percent / NaH / dimethylformamide

3.1: PCC / CH₂Cl₂

4.1: tetrahydrofuran

5.1: 98 percent / pyridine

6.1: aq. AcOH / 90 °C

7.1: pyridine

8.1: 93 percent / N,O-bis(trimethylsilyl)acetamide; TMS-triflate / acetonitrile / 60 °C

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sodium hydride; acetic acid; periodic acid; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 4.1: Grignard addition;
DOI:10.1039/b205031e

Reference yield:

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

: 485755-41-7
1-(2-O-acetyl-3-C-allyl-3,5-di-O-benzyl-4-C-(1(S)-(benzoyloxy)allyl)-β-D-ribofuranosyl)thymine

Guidance literature:: Multi-step reaction with 7 steps

1: 55 percent / NaH / dimethylformamide

2: PCC / CH₂Cl₂

3: tetrahydrofuran

4: 98 percent / pyridine

5: aq. AcOH / 90 °C

6: pyridine

7: 93 percent / N,O-bis(trimethylsilyl)acetamide; TMS-triflate / acetonitrile / 60 °C

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sodium hydride; acetic acid; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 3: Grignard addition;
DOI:10.1039/b205031e