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

Base Information

Chemical Name:(2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-((triethylsilyl)ethynyl)tetrahydrofuran-3-yl acetate
CAS No.:233266-85-8
Molecular Formula:C₃₄H₄₂N₂O₇Si
Molecular Weight:618.802
Hs Code.:

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

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

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

Chemical Property:

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

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Technology Process of (2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-((triethylsilyl)ethynyl)tetrahydrofuran-3-yl acetate

There total 8 articles about (2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-((triethylsilyl)ethynyl)tetrahydrofuran-3-yl acetate 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: 87.4%

: 65-71-4,28806-14-6,691841-57-3
thymin

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

: 233266-85-8
(2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-((triethylsilyl)ethynyl)tetrahydrofuran-3-yl acetate

Guidance literature:: With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; for 13h; Heating;
DOI:10.1021/jm000209n

Reference yield: 87.0%

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

: 233266-85-8
(2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-((triethylsilyl)ethynyl)tetrahydrofuran-3-yl acetate

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane;
DOI:10.1271/bbb.63.1146

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

: 233266-85-8
(2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-((triethylsilyl)ethynyl)tetrahydrofuran-3-yl acetate

Guidance literature:: Multi-step reaction with 7 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: 87 percent / TMSOTf / 1,2-dichloro-ethane

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