Thiocarbonic acid O-[(2R,3S,5R)-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl] ester O-phenyl ester

Base Information

• Chemical Name: Thiocarbonic acid O-[(2R,3S,5R)-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl] ester O-phenyl ester
• CAS No.: 154230-35-0
• Molecular Formula: C₄₁H₄₄N₂O₇SSi
• Molecular Weight: 736.961

Synonyms:Thiocarbonic acid O-[(2R,3S,5R)-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl] ester O-phenyl ester

Chemical Property of Thiocarbonic acid O-[(2R,3S,5R)-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl] ester O-phenyl ester

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Technology Process of Thiocarbonic acid O-[(2R,3S,5R)-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl] ester O-phenyl ester

There total 3 articles about Thiocarbonic acid O-[(2R,3S,5R)-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl] ester O-phenyl 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: 75.0%

5'-O-tert-butyldiphenylsilyl-N3-benzyloxymethyl-2'-deoxythymidine (154230-32-7) + phenylcarbonochloridothioate (1005-56-7) → Thiocarbonic acid O-[(2R,3S,5R)-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl] ester O-phenyl ester (154230-35-0)

Guidance literature:

With pyridine; 1-hydroxy-pyrrolidine-2,5-dione; In toluene; at 80 ℃;

DOI:10.1021/jo00081a003

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → Thiocarbonic acid O-[(2R,3S,5R)-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl] ester O-phenyl ester (154230-35-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / (i-Pr)2NEt / CH₂Cl₂ / 23 °C

2: 75 percent / N-hydroxysuccinimide, pyridine / toluene / 80 °C

With pyridine; 1-hydroxy-pyrrolidine-2,5-dione; N-ethyl-N,N-diisopropylamine; In dichloromethane; toluene;

DOI:10.1021/jo00081a003

Reference yield:

5'-O-tert-butyldiphenylsilylthymidine (101527-40-6) → Thiocarbonic acid O-[(2R,3S,5R)-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl] ester O-phenyl ester (154230-35-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / (i-Pr)2NEt / CH₂Cl₂ / 23 °C

2: 75 percent / N-hydroxysuccinimide, pyridine / toluene / 80 °C

With pyridine; 1-hydroxy-pyrrolidine-2,5-dione; N-ethyl-N,N-diisopropylamine; In dichloromethane; toluene;

DOI:10.1021/jo00081a003

upstream raw materials:

5'-O-tert-butyldiphenylsilyl-N³-benzyloxymethyl-2'-deoxythymidine

phenylcarbonochloridothioate

Benzyloxymethyl chloride

5'-O-tert-butyldiphenylsilylthymidine

Downstream raw materials:

C₆₁H₆₈N₄O₁₂Si

3-((Benzyloxy)methyl)-3'-deoxy-3'-(3-hydroxypropyl)-5'-O-(tert-butyldiphenylsilyl)thymidine

1-[(2R,4S,5S)-4-Allyl-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-3-benzyloxymethyl-5-methyl-1H-pyrimidine-2,4-dione

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