Technology Process of (1R,2R,5R,7R,8S)-8-benzyloxy-5-benzyloxymethyl-2-methyl-7-(thymin-1-yl)-6-oxa-bicyclo[3.2.1]octane
There total 15 articles about (1R,2R,5R,7R,8S)-8-benzyloxy-5-benzyloxymethyl-2-methyl-7-(thymin-1-yl)-6-oxa-bicyclo[3.2.1]octane which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
1-[3,5-di-O-benzyl-4-C-penten-yl-2-O-phenoxythiocarbonyl-β-D-ribofuranosyl]-thymine;
With
tri-n-butyl-tin hydride;
In
toluene;
for 0.25h;
Heating;
With
tri-n-butyl-tin hydride;
In
toluene;
for 2h;
Further stages.;
Heating;
DOI:10.1021/ja071106y
- Guidance literature:
-
Multi-step reaction with 5 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
5.1: Bu3SnH / toluene / 0.25 h / Heating
5.2: 76 percent / 2,2'-azobis(2-methyl-propionitrile; Bu3SnH / toluene / 2 h / Heating
With
pyridine; dmap; N,O-bis-(trimethylsilyl)-acetamide; trifluorormethanesulfonic acid; ammonia; tri-n-butyl-tin hydride; acetic acid;
In
methanol; toluene; acetonitrile;
2.2: Vorbrueggen reaction;
DOI:10.1021/ja071106y
- Guidance literature:
-
Multi-step reaction with 7 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
7.1: Bu3SnH / toluene / 0.25 h / Heating
7.2: 76 percent / 2,2'-azobis(2-methyl-propionitrile; Bu3SnH / toluene / 2 h / Heating
With
pyridine; dmap; n-butyllithium; N,O-bis-(trimethylsilyl)-acetamide; oxalyl dichloride; trifluorormethanesulfonic acid; ammonia; tri-n-butyl-tin hydride; acetic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; methanol; hexane; dichloromethane; toluene; acetonitrile;
1.1: Swern oxidation / 2.2: Wittig reaction / 4.2: Vorbrueggen reaction;
DOI:10.1021/ja071106y
![1-[3,5-di-O-benzyl-4-C-penten-yl-2-O-phenoxythiocarbonyl-β-D-ribofuranosyl]-thymine](/Databaselist/images/loading.webp)
