1-[5'-O-tert-butyldiphenylsilyl-2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-erythro-pentofuranosyl]-5-fluorouracil

Base Information

Chemical Name:1-[5'-O-tert-butyldiphenylsilyl-2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-erythro-pentofuranosyl]-5-fluorouracil
CAS No.:529495-87-2
Molecular Formula:C₂₉H₃₇FN₂O₄S₃Si
Molecular Weight:620.906
Hs Code.:

Synonyms:1-[5'-O-tert-butyldiphenylsilyl-2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-erythro-pentofuranosyl]-5-fluorouracil

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Chemical Property of 1-[5'-O-tert-butyldiphenylsilyl-2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-erythro-pentofuranosyl]-5-fluorouracil

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Technology Process of 1-[5'-O-tert-butyldiphenylsilyl-2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-erythro-pentofuranosyl]-5-fluorouracil

There total 4 articles about 1-[5'-O-tert-butyldiphenylsilyl-2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-erythro-pentofuranosyl]-5-fluorouracil 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: 54.0%

: 51-21-8
5-fluorouracil

: 529495-78-1
(4R,5R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[tri(methylthio)methyl]tetrahydrofuran-2-yl acetate

: 529495-87-2
1-[5'-O-tert-butyldiphenylsilyl-2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-erythro-pentofuranosyl]-5-fluorouracil

: 1-[5'-O-tert-butyldiphenylsilyl-2',3'-dideoxy-3'-C-tris(methylthio)methyl-α-L-erythro-pentofuranosyl]-5-fluorouracil

Guidance literature:: 5-fluorouracil; With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane; Heating;

(4R,5R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[tri(methylthio)methyl]tetrahydrofuran-2-yl acetate; With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 0 - 20 ℃; for 0.75h;
DOI:10.1016/S0968-0896(02)00460-1

Reference yield:

: 110171-24-9
(R)-(+)-5-(tert-butyldiphenylsilanyloxymethyl)furan-2(5H)-one

: 529495-87-2
1-[5'-O-tert-butyldiphenylsilyl-2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-erythro-pentofuranosyl]-5-fluorouracil

Guidance literature:: Multi-step reaction with 4 steps

1.1: 81 percent / n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

2.1: DIBAL / toluene; hexane / 1 h / -70 °C

3.1: 65 percent / pyridine / CH₂Cl₂ / 1.5 h / 20 °C

4.1: HMDS; (NH₄)2SO₄ / Heating

4.2: 54 percent / TMSOTf / acetonitrile / 0.75 h / 0 - 20 °C

With pyridine; ammonium sulfate; n-butyllithium; diisobutylaluminium hydride; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; dichloromethane; toluene;
DOI:10.1016/S0968-0896(02)00460-1

Reference yield:

: (4R,5R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[tri(methylthio)methyl]tetrahydrofuran-2-ol

: 529495-87-2
1-[5'-O-tert-butyldiphenylsilyl-2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-erythro-pentofuranosyl]-5-fluorouracil

Guidance literature:: Multi-step reaction with 2 steps

1.1: 65 percent / pyridine / CH₂Cl₂ / 1.5 h / 20 °C

2.1: HMDS; (NH₄)2SO₄ / Heating

2.2: 54 percent / TMSOTf / acetonitrile / 0.75 h / 0 - 20 °C

With pyridine; ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane;
DOI:10.1016/S0968-0896(02)00460-1