(3S,5R)-benzoic acid 2-acetoxy-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

Base Information

• Chemical Name: (3S,5R)-benzoic acid 2-acetoxy-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
• CAS No.: 944474-95-7
• Molecular Formula: C₂₆H₂₆N₂O₈
• Molecular Weight: 494.501

Synonyms:(3S,5R)-benzoic acid 2-acetoxy-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

Chemical Property of (3S,5R)-benzoic acid 2-acetoxy-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

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Technology Process of (3S,5R)-benzoic acid 2-acetoxy-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

There total 1 articles about (3S,5R)-benzoic acid 2-acetoxy-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 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: 86.0%

lead(IV) acetate + (2S,3S,5R)-3-benzoyloxy-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carboxylic acid (154230-41-8) → (3S,5R)-benzoic acid 2-acetoxy-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (944474-95-7)

Guidance literature:

With pyridine;

DOI:10.1080/15257770701490126

Reference yield: 82.0%

3-((Benzyloxy)methyl)-3'-O-(2-hydroxyethyl)-5'-O-(tert-butyldiphenylsilyl)thymidine (154230-34-9) + (3S,5R)-benzoic acid 2-acetoxy-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (944474-95-7) → C60H66N4O13Si (154230-45-2)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; triethylamine; In dichloromethane; at -23 ℃;

DOI:10.1021/jo00081a003

Reference yield: 78.0%

3-((Benzyloxy)methyl)-3'-deoxy-3'-(3-hydroxypropyl)-5'-O-(tert-butyldiphenylsilyl)thymidine (154230-37-2) + (3S,5R)-benzoic acid 2-acetoxy-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (944474-95-7) → C61H68N4O12Si (154230-46-3)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; triethylamine; In dichloromethane; at -23 ℃;

DOI:10.1021/jo00081a003

upstream raw materials:

(2S,3S,5R)-3-benzoyloxy-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carboxylic acid

Downstream raw materials:

C₆₁H₆₈N₄O₁₂Si

C₆₀H₆₆N₄O₁₃Si

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