8-chloro-N¹-[[[2-(phenylthio)phosphoryl]oxy-ethoxy]methyl]-5'-O-phosphoryl-2',3'-O-isopropylideneinosine

Base Information

• Chemical Name: 8-chloro-N¹-[[[2-(phenylthio)phosphoryl]oxy-ethoxy]methyl]-5'-O-phosphoryl-2',3'-O-isopropylideneinosine
• CAS No.: 444989-19-9
• Molecular Formula: C₂₂H₂₇ClN₄O₁₂P₂S
• Molecular Weight: 668.942

Synonyms:8-chloro-N¹-[[[2-(phenylthio)phosphoryl]oxy-ethoxy]methyl]-5'-O-phosphoryl-2',3'-O-isopropylideneinosine

Chemical Property of 8-chloro-N¹-[[[2-(phenylthio)phosphoryl]oxy-ethoxy]methyl]-5'-O-phosphoryl-2',3'-O-isopropylideneinosine

Chemical Property:

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Technology Process of 8-chloro-N¹-[[[2-(phenylthio)phosphoryl]oxy-ethoxy]methyl]-5'-O-phosphoryl-2',3'-O-isopropylideneinosine

There total 5 articles about 8-chloro-N¹-[[[2-(phenylthio)phosphoryl]oxy-ethoxy]methyl]-5'-O-phosphoryl-2',3'-O-isopropylideneinosine 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:

8-chloro-N1-[[[bis(phenylthio)phosphoryl]oxy-ethoxy]methyl]-5'-O-(dianilinophosphoryl)-2',3'-O-isopropylideneinosine (444989-18-8) → 8-chloro-N1-[[[2-(phenylthio)phosphoryl]oxy-ethoxy]methyl]-5'-O-phosphoryl-2',3'-O-isopropylideneinosine (444989-19-9)

Guidance literature:

8-chloro-N¹-[[[bis(phenylthio)phosphoryl]oxy-ethoxy]methyl]-5'-O-(dianilinophosphoryl)-2',3'-O-isopropylideneinosine; With acetic anhydride; acetic acid; isopentyl nitrite; In pyridine; at 20 ℃; for 8h;

With pyridine; hypophosphorous acid; triethylamine; at 20 ℃; for 11h; Further stages.;

DOI:10.1021/jm010530l

Reference yield:

5'-O-TBDMS-2',3'-O-isopropylidene-8-bromoinosine (203249-43-8) → 8-chloro-N1-[[[2-(phenylthio)phosphoryl]oxy-ethoxy]methyl]-5'-O-phosphoryl-2',3'-O-isopropylideneinosine (444989-19-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 82 percent / DBU / CH₂Cl₂ / 0.5 h / 20 °C

2.1: 90 percent / TBAF / tetrahydrofuran / 6 h / 20 °C

3.1: 84.5 percent / tetrazole; pyridine / 48 h / 20 °C

4.1: 50 mg / CH₃ONa; MeOH / 20 °C

5.1: 44 mg / pyridine; tetrazole; triisopropylbenzenesulfonyl chloride / 24 h / 20 °C

6.1: isoamylnitrite; AcOH; Ac₂O / pyridine / 8 h / 20 °C

6.2: pyridine; H₃PO₂; Et₃N / 11 h / 20 °C

With pyridine; 1H-tetrazole; methanol; triisopropylbenzenesulfonyl chloride; tetrabutyl ammonium fluoride; sodium methylate; acetic anhydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; isopentyl nitrite; In tetrahydrofuran; pyridine; dichloromethane;

DOI:10.1021/jm010530l

Reference yield:

8-bromo-N1-[(2-acetoxyethoxy)-methyl]-5'-O-(tert-butyldimethylsilyl)-2',3'-O-isopropylideneinosine (444989-14-4) → 8-chloro-N1-[[[2-(phenylthio)phosphoryl]oxy-ethoxy]methyl]-5'-O-phosphoryl-2',3'-O-isopropylideneinosine (444989-19-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 90 percent / TBAF / tetrahydrofuran / 6 h / 20 °C

2.1: 84.5 percent / tetrazole; pyridine / 48 h / 20 °C

3.1: 50 mg / CH₃ONa; MeOH / 20 °C

4.1: 44 mg / pyridine; tetrazole; triisopropylbenzenesulfonyl chloride / 24 h / 20 °C

5.1: isoamylnitrite; AcOH; Ac₂O / pyridine / 8 h / 20 °C

5.2: pyridine; H₃PO₂; Et₃N / 11 h / 20 °C

With pyridine; 1H-tetrazole; methanol; triisopropylbenzenesulfonyl chloride; tetrabutyl ammonium fluoride; sodium methylate; acetic anhydride; acetic acid; isopentyl nitrite; In tetrahydrofuran; pyridine;

DOI:10.1021/jm010530l

upstream raw materials:

8-chloro-N¹-[[[bis(phenylthio)phosphoryl]oxy-ethoxy]methyl]-5'-O-(dianilinophosphoryl)-2',3'-O-isopropylideneinosine

5'-O-TBDMS-2',3'-O-isopropylidene-8-bromoinosine

8-bromo-N¹-[(2-acetoxyethoxy)-methyl]-5'-O-(tert-butyldimethylsilyl)-2',3'-O-isopropylideneinosine

8-bromo-N¹-[(2-acetoxyethoxy)-methyl]-5'-O-dianilinophosphoryl-2',3'-O-isopropylideneinosine

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