1-(3-O-benzyl-5-O-(tert-butyldiphenylsilyl)-2-deoxy-2-fluoro-4-thio-D-arabino-pentofuranosyl)-5-iodouracil

Base Information

• Chemical Name: 1-(3-O-benzyl-5-O-(tert-butyldiphenylsilyl)-2-deoxy-2-fluoro-4-thio-D-arabino-pentofuranosyl)-5-iodouracil
• CAS No.: 207671-68-9
• Molecular Formula: C₃₂H₃₄FIN₂O₄SSi
• Molecular Weight: 716.687

Synonyms:1-(3-O-benzyl-5-O-(tert-butyldiphenylsilyl)-2-deoxy-2-fluoro-4-thio-D-arabino-pentofuranosyl)-5-iodouracil

Chemical Property of 1-(3-O-benzyl-5-O-(tert-butyldiphenylsilyl)-2-deoxy-2-fluoro-4-thio-D-arabino-pentofuranosyl)-5-iodouracil

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Technology Process of 1-(3-O-benzyl-5-O-(tert-butyldiphenylsilyl)-2-deoxy-2-fluoro-4-thio-D-arabino-pentofuranosyl)-5-iodouracil

There total 1 articles about 1-(3-O-benzyl-5-O-(tert-butyldiphenylsilyl)-2-deoxy-2-fluoro-4-thio-D-arabino-pentofuranosyl)-5-iodouracil 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: 78.0%

5-iodouracil (696-07-1) + Acetic acid (3S,4S,5R)-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-3-fluoro-tetrahydro-thiophen-2-yl ester (189748-60-5) → 1-(3-O-benzyl-5-O-(tert-butyldiphenylsilyl)-2-deoxy-2-fluoro-4-thio-D-arabino-pentofuranosyl)-5-iodouracil (207671-68-9)

Guidance literature:

5-iodouracil; With benzenesulfonamide; In acetonitrile; for 4h; Heating;

Acetic acid (3S,4S,5R)-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-3-fluoro-tetrahydro-thiophen-2-yl ester; With tin(IV) chloride; In dichloromethane; acetonitrile; for 3.5h; Heating;

DOI:10.1016/S0968-0896(00)00065-1

Reference yield: 64.0%

1-(3-O-benzyl-5-O-(tert-butyldiphenylsilyl)-2-deoxy-2-fluoro-4-thio-D-arabino-pentofuranosyl)-5-iodouracil (207671-68-9) → 1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-3-fluoro-4-hydroxy-tetrahydro-thiophen-2-yl]-4-hydroxy-5-iodo-1H-pyrimidin-2-one (294867-80-4) + 1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-3-fluoro-4-hydroxy-tetrahydro-thiophen-2-yl]-4-hydroxy-5-iodo-1H-pyrimidin-2-one (294867-78-0)

Guidance literature:

With boron tribromide; In dichloromethane; at -78 ℃; for 1.5h;

DOI:10.1016/S0968-0896(00)00065-1

upstream raw materials:

5-iodouracil

Acetic acid (3S,4S,5R)-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-3-fluoro-tetrahydro-thiophen-2-yl ester

Downstream raw materials:

1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-3-fluoro-4-hydroxy-tetrahydro-thiophen-2-yl]-4-hydroxy-5-iodo-1H-pyrimidin-2-one

1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-3-fluoro-4-hydroxy-tetrahydro-thiophen-2-yl]-4-hydroxy-5-iodo-1H-pyrimidin-2-one

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