(5'S)-3'-O-(tert-butyldiphenylsilyl)-5'-C-(methoxycarbonylmethyl)-2'-O-methyluridine

Base Information

Chemical Name:(5'S)-3'-O-(tert-butyldiphenylsilyl)-5'-C-(methoxycarbonylmethyl)-2'-O-methyluridine
CAS No.:1372710-52-5
Molecular Formula:C₂₉H₃₆N₂O₈Si
Molecular Weight:568.699
Hs Code.:

Synonyms:(5'S)-3'-O-(tert-butyldiphenylsilyl)-5'-C-(methoxycarbonylmethyl)-2'-O-methyluridine

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Chemical Property of (5'S)-3'-O-(tert-butyldiphenylsilyl)-5'-C-(methoxycarbonylmethyl)-2'-O-methyluridine

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Technology Process of (5'S)-3'-O-(tert-butyldiphenylsilyl)-5'-C-(methoxycarbonylmethyl)-2'-O-methyluridine

There total 4 articles about (5'S)-3'-O-(tert-butyldiphenylsilyl)-5'-C-(methoxycarbonylmethyl)-2'-O-methyluridine 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%

: 1372710-50-3
3'-O-(tert-butyldiphenylsilyl)-2'-O-methyl-5'-oxouridine

: 1372710-52-5
(5'S)-3'-O-(tert-butyldiphenylsilyl)-5'-C-(methoxycarbonylmethyl)-2'-O-methyluridine

Guidance literature:: 3'-O-(tert-butyldiphenylsilyl)-2'-O-methyl-5'-oxouridine; With bismuth(III) chloride; zinc(II) iodide; In dichloromethane; at 20 ℃; for 0.5h;

methyl acetate silyl ketene; In dichloromethane; for 2h; diastereoselective reaction;
DOI:10.1002/ejoc.201101353

Reference yield:

: 2140-76-3
2'-O-methyluridine

: 1372710-52-5
(5'S)-3'-O-(tert-butyldiphenylsilyl)-5'-C-(methoxycarbonylmethyl)-2'-O-methyluridine

Guidance literature:: Multi-step reaction with 3 steps

1.1: pyridine; tert-butyldimethylsilyl chloride / 12 h / 20 °C

1.2: 12 h / 20 °C

1.3: 3 h / 20 °C

2.1: dichloro-acetic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide / 16 h / 20 °C

3.1: bismuth(III) chloride; zinc(II) iodide / dichloromethane / 0.5 h / 20 °C

3.2: 2 h

With pyridine; dichloro-acetic acid; bismuth(III) chloride; tert-butyldimethylsilyl chloride; dimethyl sulfoxide; dicyclohexyl-carbodiimide; zinc(II) iodide; In dichloromethane; 2.1: Pfitzner-Moffatt oxidation / 3.1: Mukaiyama reaction / 3.2: Mukaiyama reaction;
DOI:10.1002/ejoc.201101353

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 1372710-52-5
(5'S)-3'-O-(tert-butyldiphenylsilyl)-5'-C-(methoxycarbonylmethyl)-2'-O-methyluridine

Guidance literature:: Multi-step reaction with 3 steps

1.1: pyridine; tert-butyldimethylsilyl chloride / 12 h / 20 °C

1.2: 12 h / 20 °C

1.3: 3 h / 20 °C

2.1: dichloro-acetic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide / 16 h / 20 °C

3.1: bismuth(III) chloride; zinc(II) iodide / dichloromethane / 0.5 h / 20 °C

3.2: 2 h

With pyridine; dichloro-acetic acid; bismuth(III) chloride; tert-butyldimethylsilyl chloride; dimethyl sulfoxide; dicyclohexyl-carbodiimide; zinc(II) iodide; In dichloromethane; 2.1: Pfitzner-Moffatt oxidation / 3.1: Mukaiyama reaction / 3.2: Mukaiyama reaction;
DOI:10.1002/ejoc.201101353