2-[(2S,3R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-N-[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-acetamide

Base Information

• Chemical Name: 2-[(2S,3R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-N-[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-acetamide
• CAS No.: 151807-43-1
• Molecular Formula: C₃₈H₄₇N₅O₉Si
• Molecular Weight: 745.905

Synonyms:2-[(2S,3R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-N-[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-acetamide

Chemical Property of 2-[(2S,3R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-N-[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-acetamide

Chemical Property:

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Technology Process of 2-[(2S,3R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-N-[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-acetamide

There total 11 articles about 2-[(2S,3R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-N-[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-acetamide 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: 80.0%

5'-amino-5'-deoxythymidine (25152-20-9) + 5'-O-(tert-butyldiphenylsilyl)-3'-C-methylenecarboxylic-3'-deoxythymidine (146557-61-1) → 2-[(2S,3R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-N-[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-acetamide (151807-43-1)

Guidance literature:

With TEA; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; In N,N-dimethyl-formamide; for 0.5h;

DOI:10.1016/S0040-4039(00)73923-2

Reference yield:

5'-O-(tert-butyldiphenylsilyl)-3'-C-methyleneformyl-3'-deoxythymidine (146557-59-7) → 2-[(2S,3R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-N-[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-acetamide (151807-43-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) pyridinium dichromate, 2.) NaOH / 1.) MeOH, DMF, RT, overnight, 2.) MeOH, RT, overnight

2: 1.) N-methylmorpholine, O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium tetrafluoroborate, 1-hydroxybenzotriazole, 2.) N-methylmorpholine / 1.) DMF, RT, 2 h, 2.) DMF

With 4-methyl-morpholine; sodium hydroxide; dipyridinium dichromate; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate;

DOI:10.1016/S0960-894X(99)00052-9

Reference yield:

3-C-allyl-1-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-erythro-pentofuranosyl]thymine (146557-58-6) → 2-[(2S,3R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-N-[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-acetamide (151807-43-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 55 percent / OsO₄, NaIO₄ / dioxane; H₂O / 6 h / Ambient temperature

2: 1.) pyridinium dichromate, 2.) NaOH / 1.) MeOH, DMF, RT, overnight, 2.) MeOH, RT, overnight

3: 1.) N-methylmorpholine, O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium tetrafluoroborate, 1-hydroxybenzotriazole, 2.) N-methylmorpholine / 1.) DMF, RT, 2 h, 2.) DMF

With 4-methyl-morpholine; sodium hydroxide; sodium periodate; osmium(VIII) oxide; dipyridinium dichromate; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; In 1,4-dioxane; water;

DOI:10.1016/S0960-894X(99)00052-9

upstream raw materials:

5'-amino-5'-deoxythymidine

5'-O-(tert-butyldiphenylsilyl)-3'-C-methylenecarboxylic-3'-deoxythymidine

5'-O-(p-toluenesulfonyl)thymidine

5'-O-tert-butyldiphenylsilylthymidine

Downstream raw materials:

C₄₃H₄₇N₅O₁₁

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