1-((2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-3-hydroxy-5-((triethylsilyl)ethynyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

Base Information

Chemical Name:1-((2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-3-hydroxy-5-((triethylsilyl)ethynyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
CAS No.:233266-95-0
Molecular Formula:C₃₁H₃₈N₂O₆Si
Molecular Weight:562.738
Hs Code.:

Synonyms:1-((2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-3-hydroxy-5-((triethylsilyl)ethynyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 1-((2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-3-hydroxy-5-((triethylsilyl)ethynyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

Chemical Property:

Purity/Quality:: 97% ^*data from raw suppliers

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Technology Process of 1-((2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-3-hydroxy-5-((triethylsilyl)ethynyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

There total 9 articles about 1-((2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-3-hydroxy-5-((triethylsilyl)ethynyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-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: 92.5%

: 233266-86-9
(2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-((triethylsilyl)ethynyl)tetrahydrofuran-3-yl acetate

: 233266-95-0
1-((2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-3-hydroxy-5-((triethylsilyl)ethynyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

Guidance literature:: With triethylamine; In methanol;
DOI:10.1271/bbb.63.1146

Reference yield:

: 233266-82-5
1,2-di-O-acetyl-3,5-di-O-benzyl-4-C-triethylsilylethynyl-D-ribo-pentofuranose

: 233266-95-0
1-((2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-3-hydroxy-5-((triethylsilyl)ethynyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

Guidance literature:: Multi-step reaction with 2 steps

1: 76.1 percent / N,O-bis(trimethylsilyl)acetamide; trimethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / 13 h / Heating

2: 92.5 percent / triethylamine; methanol / 12 h / 20 °C

With methanol; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; triethylamine; In 1,2-dichloro-ethane;
DOI:10.1021/jm000209n

Reference yield:

: 153186-10-8
((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol

: 233266-95-0
1-((2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-3-hydroxy-5-((triethylsilyl)ethynyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

Guidance literature:: Multi-step reaction with 8 steps

1: 99 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂

2: 82 percent / PPh₃ / CH₂Cl₂

3: 88 percent / n-BuLi / tetrahydrofuran

4: 98 percent / n-BuLi / tetrahydrofuran

5: AcOH / H₂O

6: 80 percent / pyridine

7: 76 percent / TMSOTf / 1,2-dichloro-ethane

8: 92 percent / Et₃N / methanol

With n-butyllithium; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; 1,2-dichloro-ethane; 1: Oxidation / 2: Substitution / 3: Elimination / 4: Substitution / 5: Hydrolysis / 6: Acetoxylation / 7: Substitution / 8: Hydrolysis;
DOI:10.1271/bbb.63.1146