3-Benzyloxymethyl-1-[(2R,3R,4R,5R)-4-(2,4-dichloro-benzyloxy)-5-(2,4-dichloro-benzyloxymethyl)-3-((R)-1-oxiranylmethoxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

Base Information

Chemical Name:3-Benzyloxymethyl-1-[(2R,3R,4R,5R)-4-(2,4-dichloro-benzyloxy)-5-(2,4-dichloro-benzyloxymethyl)-3-((R)-1-oxiranylmethoxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
CAS No.:163759-70-4
Molecular Formula:C₃₅H₃₄Cl₄N₂O₈
Molecular Weight:752.476
Hs Code.:

3-Benzyloxymethyl-1-[(2R,3R,4R,5R)-4-(2,4-dichloro-benzyloxy)-5-(2,4-dichloro-benzyloxymethyl)-3-((R)-1-oxiranylmethoxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

Synonyms:3-Benzyloxymethyl-1-[(2R,3R,4R,5R)-4-(2,4-dichloro-benzyloxy)-5-(2,4-dichloro-benzyloxymethyl)-3-((R)-1-oxiranylmethoxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

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Chemical Property of 3-Benzyloxymethyl-1-[(2R,3R,4R,5R)-4-(2,4-dichloro-benzyloxy)-5-(2,4-dichloro-benzyloxymethyl)-3-((R)-1-oxiranylmethoxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

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Technology Process of 3-Benzyloxymethyl-1-[(2R,3R,4R,5R)-4-(2,4-dichloro-benzyloxy)-5-(2,4-dichloro-benzyloxymethyl)-3-((R)-1-oxiranylmethoxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

There total 8 articles about 3-Benzyloxymethyl-1-[(2R,3R,4R,5R)-4-(2,4-dichloro-benzyloxy)-5-(2,4-dichloro-benzyloxymethyl)-3-((R)-1-oxiranylmethoxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 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: 72.0%

: 113826-06-5,6746-81-2
(R)-glycidyl tosylate

: 163759-45-3
3-<(Benzyloxy)methyl>-1-<3',5'-bis-O-(2,4-dichlorobenzyl)-β-D-ribofuranosyl>thymin

: 163759-70-4
3-Benzyloxymethyl-1-[(2R,3R,4R,5R)-4-(2,4-dichloro-benzyloxy)-5-(2,4-dichloro-benzyloxymethyl)-3-((R)-1-oxiranylmethoxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

Guidance literature:: With sodium hydride; In tetrahydrofuran; at 40 - 70 ℃;
DOI:10.1002/hlca.19950780219

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 163759-70-4
3-Benzyloxymethyl-1-[(2R,3R,4R,5R)-4-(2,4-dichloro-benzyloxy)-5-(2,4-dichloro-benzyloxymethyl)-3-((R)-1-oxiranylmethoxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 3 steps

1: 1,8-diazabicyclo<5.4.0>undec-7-ene / acetonitrile / 10 h

2: 98 percent / 30percent NaOMe / methanol / 3 h / Ambient temperature

3: 72 percent / NaH / tetrahydrofuran / 40 - 70 °C

With sodium methylate; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; acetonitrile;
DOI:10.1002/hlca.19950780219

Reference yield:

: 50-69-1
D-ribose

: 163759-70-4
3-Benzyloxymethyl-1-[(2R,3R,4R,5R)-4-(2,4-dichloro-benzyloxy)-5-(2,4-dichloro-benzyloxymethyl)-3-((R)-1-oxiranylmethoxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) cc. H₂SO₄, 2.) NaH / 1.) 4 deg C, 16 h, 2.) DMF, 40 deg C

2: 125.9 g / SnCl₄ / CH₂Cl₂ / 35 h / 3 °C

3: pyridine, 4-(dimethylamino)-pyridine / 17 h

4: 1.) N,O-bis(trimethylsilyl)acetamide, 2.) TfOSiMe₃ / 1.) ClCH₂CH₂Cl, reflux, 10 min, 2.) ClCH₂CH₂Cl, 70 deg C, 20 h

5: 1,8-diazabicyclo<5.4.0>undec-7-ene / acetonitrile / 10 h

6: 98 percent / 30percent NaOMe / methanol / 3 h / Ambient temperature

7: 72 percent / NaH / tetrahydrofuran / 40 - 70 °C

With pyridine; dmap; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; sodium methylate; tin(IV) chloride; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;
DOI:10.1002/hlca.19950780219