N¹-[5''-O-(phenylthio)phosphoryl-2''-deoxy-3''-O-allyl-D-lyxitol-2''-yl]-5'-O-phosphoryl-2',3'-di-O-acetylinosine

Base Information

• Chemical Name: N¹-[5''-O-(phenylthio)phosphoryl-2''-deoxy-3''-O-allyl-D-lyxitol-2''-yl]-5'-O-phosphoryl-2',3'-di-O-acetylinosine
• CAS No.: 478044-49-4
• Molecular Formula: C₂₈H₃₃BrN₄O₁₅P₂S
• Molecular Weight: 839.505

Synonyms:N¹-[5''-O-(phenylthio)phosphoryl-2''-deoxy-3''-O-allyl-D-lyxitol-2''-yl]-5'-O-phosphoryl-2',3'-di-O-acetylinosine

Chemical Property of N¹-[5''-O-(phenylthio)phosphoryl-2''-deoxy-3''-O-allyl-D-lyxitol-2''-yl]-5'-O-phosphoryl-2',3'-di-O-acetylinosine

Chemical Property:

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Technology Process of N¹-[5''-O-(phenylthio)phosphoryl-2''-deoxy-3''-O-allyl-D-lyxitol-2''-yl]-5'-O-phosphoryl-2',3'-di-O-acetylinosine

There total 8 articles about N¹-[5''-O-(phenylthio)phosphoryl-2''-deoxy-3''-O-allyl-D-lyxitol-2''-yl]-5'-O-phosphoryl-2',3'-di-O-acetylinosine 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: 70.0%

8-bromo-N1-[5''-O-[bis-(phenylthio)phosphoryl]-1'',4''-anhydro-2''-deoxy-3''-O-allyl-D-lyxitol-2''-yl]-5'-O-(dianilinophosphoryl)-2',3'-di-O-acetylinosine (478044-34-7) → N1-[5''-O-(phenylthio)phosphoryl-2''-deoxy-3''-O-allyl-D-lyxitol-2''-yl]-5'-O-phosphoryl-2',3'-di-O-acetylinosine (478044-49-4)

Guidance literature:

8-bromo-N¹-[5''-O-[bis-(phenylthio)phosphoryl]-1'',4''-anhydro-2''-deoxy-3''-O-allyl-D-lyxitol-2''-yl]-5'-O-(dianilinophosphoryl)-2',3'-di-O-acetylinosine; 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:

dithiophenoxyphosphoryl chloride (273387-14-7) → N1-[5''-O-(phenylthio)phosphoryl-2''-deoxy-3''-O-allyl-D-lyxitol-2''-yl]-5'-O-phosphoryl-2',3'-di-O-acetylinosine (478044-49-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 96.3 percent / tetrazole; pyridine; triisopropylbenzenesulfonyl chloride / 72 h / 20 °C

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

2.2: 70 percent / pyridine; H₃PO₂; Et₃N / 11 h / 20 °C

With pyridine; 1H-tetrazole; triisopropylbenzenesulfonyl chloride; acetic anhydride; acetic acid; isopentyl nitrite; In pyridine;

DOI:10.1021/jm010530l

Reference yield:

(3S,4R,5R)-4-Allyloxy-5-hydroxymethyl-tetrahydro-furan-3-ol → N1-[5''-O-(phenylthio)phosphoryl-2''-deoxy-3''-O-allyl-D-lyxitol-2''-yl]-5'-O-phosphoryl-2',3'-di-O-acetylinosine (478044-49-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 6.05 g / pyridine / 48 h / 20 °C

2.1: pyridine / -15 °C

3.1: K₂CO₃; 18-crown-6 / tetrahydrofuran / 1 h / Heating

3.2: 34 percent / tetrahydrofuran / 24 h / 45 °C

4.1: 86 percent / TBAF / tetrahydrofuran / 6 h / 20 °C

5.1: 95 percent / tetrazole; pyridine / 48 h / 20 °C

6.1: 79.6 percent / 5percent aq. Cl₃CCOOH / CH₂Cl₂ / 0.5 h

7.1: 96.3 percent / tetrazole; pyridine; triisopropylbenzenesulfonyl chloride / 72 h / 20 °C

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

8.2: 70 percent / pyridine; H₃PO₂; Et₃N / 11 h / 20 °C

With pyridine; 1H-tetrazole; 18-crown-6 ether; triisopropylbenzenesulfonyl chloride; tetrabutyl ammonium fluoride; acetic anhydride; potassium carbonate; acetic acid; isopentyl nitrite; In tetrahydrofuran; pyridine; dichloromethane;

DOI:10.1021/jm010530l

upstream raw materials:

8-bromo-N¹-[5''-O-[bis-(phenylthio)phosphoryl]-1'',4''-anhydro-2''-deoxy-3''-O-allyl-D-lyxitol-2''-yl]-5'-O-(dianilinophosphoryl)-2',3'-di-O-acetylinosine

dithiophenoxyphosphoryl chloride

5-O-(monomethoxytrityl)-3-O-allyl-1,4-anhydro-D-xylitol

Trifluoro-methanesulfonic acid (3S,4S,5R)-4-allyloxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-3-yl ester

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