3'α-diethylphosphono-3'β-hydroxy-2'-O-tert-butyldimethylsilyl-5'-O-trityluridine

Base Information

• Chemical Name: 3'α-diethylphosphono-3'β-hydroxy-2'-O-tert-butyldimethylsilyl-5'-O-trityluridine
• CAS No.: 170299-30-6
• Molecular Formula: C₃₈H₄₉N₂O₉PSi
• Molecular Weight: 736.874

Synonyms:3'α-diethylphosphono-3'β-hydroxy-2'-O-tert-butyldimethylsilyl-5'-O-trityluridine

Chemical Property of 3'α-diethylphosphono-3'β-hydroxy-2'-O-tert-butyldimethylsilyl-5'-O-trityluridine

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Technology Process of 3'α-diethylphosphono-3'β-hydroxy-2'-O-tert-butyldimethylsilyl-5'-O-trityluridine

There total 1 articles about 3'α-diethylphosphono-3'β-hydroxy-2'-O-tert-butyldimethylsilyl-5'-O-trityluridine 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: 91.0%

phosphonic acid diethyl ester (762-04-9) + 3'-keto-2'-O-tert-butyldimethylsilyl-5'-O-trityluridine → 3'α-diethylphosphono-3'β-hydroxy-2'-O-tert-butyldimethylsilyl-5'-O-trityluridine (170299-30-6)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - 0 ℃; for 2h;

DOI:10.1016/0040-4020(95)00363-D

Reference yield: 68.0%

3'α-diethylphosphono-3'β-hydroxy-2'-O-tert-butyldimethylsilyl-5'-O-trityluridine (170299-30-6) → [(2R,3S,4S,5R)-5-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-2-trityloxymethyl-tetrahydro-furan-3-yl]-phosphonic acid diethyl ester (181256-68-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; 1.) 0 deg C, 2 h, 2.) RT, 1h;

DOI:10.1016/0040-4020(96)00684-9

Reference yield:

monomethyl oxalyl chloride (5781-53-3) + 3'α-diethylphosphono-3'β-hydroxy-2'-O-tert-butyldimethylsilyl-5'-O-trityluridine (170299-30-6) → Oxalic acid (2R,3R,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-3-(diethoxy-phosphoryl)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yl ester methyl ester

Guidance literature:

With dmap; In acetonitrile; at 6 - 10 ℃; for 1h;

DOI:10.1016/0040-4020(95)00363-D

upstream raw materials:

phosphonic acid diethyl ester

Downstream raw materials:

[(2R,3S,4S,5R)-5-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-2-trityloxymethyl-tetrahydro-furan-3-yl]-phosphonic acid diethyl ester

[(1R,2R,4R,5R)-4-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-3,6-dioxa-bicyclo[3.1.0]hex-1-yl]-phosphonic acid diethyl ester

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