3',5'-di-O-benzyl-2'-O-(4-tert-butylbenzoyl)-2'-C-β-ethoxymethyluridine

Base Information

Chemical Name:3',5'-di-O-benzyl-2'-O-(4-tert-butylbenzoyl)-2'-C-β-ethoxymethyluridine
CAS No.:948838-16-2
Molecular Formula:C₃₇H₄₂N₂O₈
Molecular Weight:642.749
Hs Code.:

Synonyms:3',5'-di-O-benzyl-2'-O-(4-tert-butylbenzoyl)-2'-C-β-ethoxymethyluridine

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Chemical Property of 3',5'-di-O-benzyl-2'-O-(4-tert-butylbenzoyl)-2'-C-β-ethoxymethyluridine

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Technology Process of 3',5'-di-O-benzyl-2'-O-(4-tert-butylbenzoyl)-2'-C-β-ethoxymethyluridine

There total 7 articles about 3',5'-di-O-benzyl-2'-O-(4-tert-butylbenzoyl)-2'-C-β-ethoxymethyluridine 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: 68.0%

: 948838-13-9
methyl 3,5-di-O-benzyl-2-O-(4-tert-butylbenzoyl)-2-C-β-ethoxymethyl-α-D-ribofuranoside

: 66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6
uracil

: 948838-16-2
3',5'-di-O-benzyl-2'-O-(4-tert-butylbenzoyl)-2'-C-β-ethoxymethyluridine

Guidance literature:: uracil; With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane; for 0.5h; Heating;

methyl 3,5-di-O-benzyl-2-O-(4-tert-butylbenzoyl)-2-C-β-ethoxymethyl-α-D-ribofuranoside; With tin(IV) chloride; In acetonitrile; at 20 ℃; for 24h; Further stages.;
DOI:10.1021/ol071075b

Reference yield:

: 80795-53-5
(2S,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-methoxytetrahydrofuran-3-ol

: 948838-16-2
3',5'-di-O-benzyl-2'-O-(4-tert-butylbenzoyl)-2'-C-β-ethoxymethyluridine

Guidance literature:: Multi-step reaction with 4 steps

1.1: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 24 h / 20 °C

2.1: HgCl₂; magnesium / tetrahydrofuran / 2 h / -20 °C

2.2: tetrahydrofuran / 40 h / -78 - 20 °C

3.1: 416 mg / DMAP; triethylamine / CH₂Cl₂ / 72 h / 20 °C

4.1: 1,1,1,3,3,3-hexamethyldisilazane; ammonium sulfate / 0.5 h / Heating

4.2: 68 percent / tin(IV) chloride / acetonitrile / 24 h / 20 °C

With dmap; ammonium sulfate; Dess-Martin periodane; magnesium; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; mercury dichloride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol071075b

Reference yield:

: 885592-69-8
(2S,4R,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-methoxydihydrofuran-3(2H)-one

: 948838-16-2
3',5'-di-O-benzyl-2'-O-(4-tert-butylbenzoyl)-2'-C-β-ethoxymethyluridine

Guidance literature:: Multi-step reaction with 3 steps

1.1: HgCl₂; magnesium / tetrahydrofuran / 2 h / -20 °C

1.2: tetrahydrofuran / 40 h / -78 - 20 °C

2.1: 416 mg / DMAP; triethylamine / CH₂Cl₂ / 72 h / 20 °C

3.1: 1,1,1,3,3,3-hexamethyldisilazane; ammonium sulfate / 0.5 h / Heating

3.2: 68 percent / tin(IV) chloride / acetonitrile / 24 h / 20 °C

With dmap; ammonium sulfate; magnesium; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; mercury dichloride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol071075b