1-[3,5-di-O-benzyl-4-C-penten-yl-2-O-phenoxythiocarbonyl-β-D-ribofuranosyl]-thymine

Base Information

Chemical Name:1-[3,5-di-O-benzyl-4-C-penten-yl-2-O-phenoxythiocarbonyl-β-D-ribofuranosyl]-thymine
CAS No.:945383-18-6
Molecular Formula:C₃₅H₃₆N₂O₇S
Molecular Weight:628.746
Hs Code.:

Synonyms:1-[3,5-di-O-benzyl-4-C-penten-yl-2-O-phenoxythiocarbonyl-β-D-ribofuranosyl]-thymine

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Chemical Property of 1-[3,5-di-O-benzyl-4-C-penten-yl-2-O-phenoxythiocarbonyl-β-D-ribofuranosyl]-thymine

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Technology Process of 1-[3,5-di-O-benzyl-4-C-penten-yl-2-O-phenoxythiocarbonyl-β-D-ribofuranosyl]-thymine

There total 14 articles about 1-[3,5-di-O-benzyl-4-C-penten-yl-2-O-phenoxythiocarbonyl-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: 60.0%

: 945383-16-4
1-[3,5-di-O-benzyl-4-C-penten-yl-2-hydroxy-β-D-ribofuranosyl]-thymine

: 1005-56-7
phenylcarbonochloridothioate

: 945383-18-6
1-[3,5-di-O-benzyl-4-C-penten-yl-2-O-phenoxythiocarbonyl-β-D-ribofuranosyl]-thymine

Guidance literature:: With pyridine; dmap;
DOI:10.1021/ja071106y

Reference yield:

: 945383-12-0
3,5-di-O-benzyl-4-C-penten-yl-1,2-O-isopropylidene-α-D-ribofuranose

: 945383-18-6
1-[3,5-di-O-benzyl-4-C-penten-yl-2-O-phenoxythiocarbonyl-β-D-ribofuranosyl]-thymine

Guidance literature:: Multi-step reaction with 4 steps

1.1: acetic acid; triflic acid / 0.5 h / ice bath

2.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.75 h / Heating

2.2: TMSOTf / acetonitrile / 0 - 20 °C

3.1: 2.8 g / ammonia / methanol

4.1: 60 percent / DMAP; pyridine

With pyridine; dmap; N,O-bis-(trimethylsilyl)-acetamide; trifluorormethanesulfonic acid; ammonia; acetic acid; In methanol; acetonitrile; 2.2: Vorbrueggen reaction;
DOI:10.1021/ja071106y

Reference yield:

: 945383-09-5
3,5-di-O-benzyl-4-C-hydroxypropyl-1,2-O-isopropylidene-α-D-ribofuranose

: 945383-18-6
1-[3,5-di-O-benzyl-4-C-penten-yl-2-O-phenoxythiocarbonyl-β-D-ribofuranosyl]-thymine

Guidance literature:: Multi-step reaction with 6 steps

1.1: oxalyl chloride; DMSO; diisopropylethylamine / CH₂Cl₂ / -78 - 20 °C

2.1: BuLi / tetrahydrofuran; hexane / -78 °C

2.2: 3.5 g / tetrahydrofuran; hexane

3.1: acetic acid; triflic acid / 0.5 h / ice bath

4.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.75 h / Heating

4.2: TMSOTf / acetonitrile / 0 - 20 °C

5.1: 2.8 g / ammonia / methanol

6.1: 60 percent / DMAP; pyridine

With pyridine; dmap; n-butyllithium; N,O-bis-(trimethylsilyl)-acetamide; oxalyl dichloride; trifluorormethanesulfonic acid; ammonia; acetic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; acetonitrile; 1.1: Swern oxidation / 2.2: Wittig reaction / 4.2: Vorbrueggen reaction;
DOI:10.1021/ja071106y