N-1-{(1R,2S,3S,4R)-2-(methoxymethoxy)-3-methoxy-4-[bis(4-methoxyphenyl)(phenyl)methoxymethyl]cyclopentyl}-5'-O-{bis(phenylsulfanyl)phosphoryl}-2',3'-O-isopropylideneadenosine

Base Information

• Chemical Name: N-1-{(1R,2S,3S,4R)-2-(methoxymethoxy)-3-methoxy-4-[bis(4-methoxyphenyl)(phenyl)methoxymethyl]cyclopentyl}-5'-O-{bis(phenylsulfanyl)phosphoryl}-2',3'-O-isopropylideneadenosine
• CAS No.: 933060-66-3
• Molecular Formula: C₅₅H₆₀N₅O₁₁PS₂
• Molecular Weight: 1062.21

Synonyms:N-1-{(1R,2S,3S,4R)-2-(methoxymethoxy)-3-methoxy-4-[bis(4-methoxyphenyl)(phenyl)methoxymethyl]cyclopentyl}-5'-O-{bis(phenylsulfanyl)phosphoryl}-2',3'-O-isopropylideneadenosine

Chemical Property of N-1-{(1R,2S,3S,4R)-2-(methoxymethoxy)-3-methoxy-4-[bis(4-methoxyphenyl)(phenyl)methoxymethyl]cyclopentyl}-5'-O-{bis(phenylsulfanyl)phosphoryl}-2',3'-O-isopropylideneadenosine

Chemical Property:

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Technology Process of N-1-{(1R,2S,3S,4R)-2-(methoxymethoxy)-3-methoxy-4-[bis(4-methoxyphenyl)(phenyl)methoxymethyl]cyclopentyl}-5'-O-{bis(phenylsulfanyl)phosphoryl}-2',3'-O-isopropylideneadenosine

There total 10 articles about N-1-{(1R,2S,3S,4R)-2-(methoxymethoxy)-3-methoxy-4-[bis(4-methoxyphenyl)(phenyl)methoxymethyl]cyclopentyl}-5'-O-{bis(phenylsulfanyl)phosphoryl}-2',3'-O-isopropylideneadenosine 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: 62.0%

N-1-{(1R,2S,3S,4R)-2-(methoxymethoxy)-3-methoxy-4-[bis(4-methoxyphenyl)(phenyl)methoxymethyl]cyclopentyl}-2',3'-O-isopropylideneadenosine (933060-63-0) + (S,S')-diphenylphosphorodithioate (23282-01-1) → N-1-{(1R,2S,3S,4R)-2-(methoxymethoxy)-3-methoxy-4-[bis(4-methoxyphenyl)(phenyl)methoxymethyl]cyclopentyl}-5'-O-{bis(phenylsulfanyl)phosphoryl}-2',3'-O-isopropylideneadenosine (933060-66-3)

Guidance literature:

With pyridine; 2,4,6-triisopropylphenylsulfonyl chloride; at 20 ℃; for 1h;

DOI:10.1080/15257770600685867

Reference yield:

(CH3)3COCONHC5H7OCH2OHOCH2OCH3 → N-1-{(1R,2S,3S,4R)-2-(methoxymethoxy)-3-methoxy-4-[bis(4-methoxyphenyl)(phenyl)methoxymethyl]cyclopentyl}-5'-O-{bis(phenylsulfanyl)phosphoryl}-2',3'-O-isopropylideneadenosine (933060-66-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 91 percent / imidazole; 4-(dimethylamino)pyridine / dimethylformamide / 4 h / 20 °C

2: 74 percent / Ph₃P; DIAD / toluene / 6 h / 20 °C

3: 88 percent / MeONa / methanol / 0.5 h / 20 °C

4: 49 percent / 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 12 h / 20 °C

5: 90 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

6: 100 percent / H₂O / Heating

7: 84 percent / K₂CO₃ / methanol / 20 °C

8: 100 percent / pyridine / 20 °C

9: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 20 °C

10: 62 percent / 2,4,6-triisopropylbenzenesulfonyl chloride; pyridine / 1 h / 20 °C

With pyridine; 1H-imidazole; dmap; 2,4,6-triisopropylphenylsulfonyl chloride; 2,6-di-tert-butyl-4-methylpyridine; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; water; sodium methylate; potassium carbonate; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 2: Mitsunobu reaction;

DOI:10.1080/15257770600685867

Reference yield:

(CH3)3CSi(CH3)2OCH2C5H4O3(CH3)2C5H3N5C5H6CH2OC(C6H4OCH3)2C6H5OCH3OCH2OCH3 → N-1-{(1R,2S,3S,4R)-2-(methoxymethoxy)-3-methoxy-4-[bis(4-methoxyphenyl)(phenyl)methoxymethyl]cyclopentyl}-5'-O-{bis(phenylsulfanyl)phosphoryl}-2',3'-O-isopropylideneadenosine (933060-66-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 20 °C

2: 62 percent / 2,4,6-triisopropylbenzenesulfonyl chloride; pyridine / 1 h / 20 °C

With pyridine; 2,4,6-triisopropylphenylsulfonyl chloride; tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1080/15257770600685867

upstream raw materials:

N-1-{(1R,2S,3S,4R)-2-(methoxymethoxy)-3-methoxy-4-[bis(4-methoxyphenyl)(phenyl)methoxymethyl]cyclopentyl}-2',3'-O-isopropylideneadenosine

(S,S')-diphenylphosphorodithioate

(1R,2S,3S,4R)-1-tert-butoxycarbonylamino-2-(methoxymethoxy)-3-methoxy-4-(hydroxymethyl)cyclopentane

(1R,2S,3S,4R)-1-amino-2-(methoxymethoxy)-3-methoxy-4-(hydroxymethyl)cyclopentane

Downstream raw materials:

N-1-[(1R,2S,3S,4R)-2-(methoxymethoxy)-3-methoxy-4-(hydroxymethyl)cyclopentyl]-5'-O-{bis(phenylsulfanyl)phosphoryl}-2',3'-O-isopropylideneadenosine

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