1-(5-O-tert-butyldiphenylsilyl-2,3-dideoxy-2,3-endo-methylene-β-D-pentofuranosyl)uracil

Base Information

Chemical Name:1-(5-O-tert-butyldiphenylsilyl-2,3-dideoxy-2,3-endo-methylene-β-D-pentofuranosyl)uracil
CAS No.:260409-11-8
Molecular Formula:C₂₆H₃₀N₂O₄Si
Molecular Weight:462.621
Hs Code.:

Synonyms:1-(5-O-tert-butyldiphenylsilyl-2,3-dideoxy-2,3-endo-methylene-β-D-pentofuranosyl)uracil

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Chemical Property of 1-(5-O-tert-butyldiphenylsilyl-2,3-dideoxy-2,3-endo-methylene-β-D-pentofuranosyl)uracil

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Technology Process of 1-(5-O-tert-butyldiphenylsilyl-2,3-dideoxy-2,3-endo-methylene-β-D-pentofuranosyl)uracil

There total 6 articles about 1-(5-O-tert-butyldiphenylsilyl-2,3-dideoxy-2,3-endo-methylene-β-D-pentofuranosyl)uracil 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: 43.0%

: 66-22-8
4-Hydroxy-1H-pyrimidin-2-one

: 201853-29-4
α-5-O-tert-butyldiphenylsilyl-D-2,3-dideoxy-2,3-endo-methylenepentofuranosyl chloride

: 260409-30-1
1-(5-O-tert-butyldiphenylsilyl-2,3-dideoxy-2,3-endo-methylene-α-D-pentofuranosyl)uracil

: 260409-11-8
1-(5-O-tert-butyldiphenylsilyl-2,3-dideoxy-2,3-endo-methylene-β-D-pentofuranosyl)uracil

Guidance literature:: 4-Hydroxy-1H-pyrimidin-2-one; With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane; for 18h; Heating;

α-5-O-tert-butyldiphenylsilyl-D-2,3-dideoxy-2,3-endo-methylenepentofuranosyl chloride; In dichloromethane; at 20 ℃; for 3h; Further stages.;
DOI:10.1021/jo991212l

Reference yield:

: 153861-49-5
(1R,2S,4'S)-1-(2',2'-dimethyl-1',3'-dioxolane-4'-yl)-2-(hydroxymethyl)cyclopropane

: 260409-11-8
1-(5-O-tert-butyldiphenylsilyl-2,3-dideoxy-2,3-endo-methylene-β-D-pentofuranosyl)uracil

Guidance literature:: Multi-step reaction with 6 steps

1.1: DMSO; oxalic chloride; Et₃N / CH₂Cl₂ / 0.25 h / -78 °C

2.1: 0.1 N HCl / dioxane / 4 h / 20 °C

3.1: pyridine / CH₂Cl₂ / 24 h / 0 - 20 °C

4.1: 87 percent / pyridine / 0.5 h

5.1: HCl / diethyl ether / 0.17 h / -10 °C

6.1: HMDS; (NH₄)2SO₄ / 18 h / Heating

6.2: 43 percent / CH₂Cl₂ / 3 h / 20 °C

With pyridine; hydrogenchloride; ammonium sulfate; oxalyl dichloride; dimethyl sulfoxide; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In 1,4-dioxane; pyridine; diethyl ether; dichloromethane; 1.1: Oxidation / 2.1: Cyclization / 3.1: silylation / 4.1: Acetylation / 5.1: Substitution / 6.1: silylation / 6.2: Condensation;
DOI:10.1021/jo991212l

Reference yield:

: α/β-5-O-tert-butyldiphenylsilyl-D-2,3-dideoxy-2,3-endo-methylenepentofuranose

: 260409-11-8
1-(5-O-tert-butyldiphenylsilyl-2,3-dideoxy-2,3-endo-methylene-β-D-pentofuranosyl)uracil

Guidance literature:: Multi-step reaction with 3 steps

1.1: 87 percent / pyridine / 0.5 h

2.1: HCl / diethyl ether / 0.17 h / -10 °C

3.1: HMDS; (NH₄)2SO₄ / 18 h / Heating

3.2: 43 percent / CH₂Cl₂ / 3 h / 20 °C

With hydrogenchloride; ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane; In pyridine; diethyl ether; 1.1: Acetylation / 2.1: Substitution / 3.1: silylation / 3.2: Condensation;
DOI:10.1021/jo991212l