N6-n-octanoyl-3',5'-di-O-benzyl-2'-deoxy-2'-C-α-phthalimidomethyladenosine

Base Information

Chemical Name:N6-n-octanoyl-3',5'-di-O-benzyl-2'-deoxy-2'-C-α-phthalimidomethyladenosine
CAS No.:1394848-47-5
Molecular Formula:C₄₁H₄₄N₆O₆
Molecular Weight:716.837
Hs Code.:

Synonyms:N6-n-octanoyl-3',5'-di-O-benzyl-2'-deoxy-2'-C-α-phthalimidomethyladenosine

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of N6-n-octanoyl-3',5'-di-O-benzyl-2'-deoxy-2'-C-α-phthalimidomethyladenosine

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Technology Process of N6-n-octanoyl-3',5'-di-O-benzyl-2'-deoxy-2'-C-α-phthalimidomethyladenosine

There total 12 articles about N6-n-octanoyl-3',5'-di-O-benzyl-2'-deoxy-2'-C-α-phthalimidomethyladenosine 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: 68.0%

: 61255-42-3
C₁₉H₃₅N₅OSi₂

: 1394848-33-9
methyl 3,5-di-O-benzyl-2-deoxy-2-α-phthalimidomethyl-α-D-ribofuranoside

: 1394848-47-5
N6-n-octanoyl-3',5'-di-O-benzyl-2'-deoxy-2'-C-α-phthalimidomethyladenosine

Guidance literature:: C₁₉H₃₅N₅OSi₂; methyl 3,5-di-O-benzyl-2-deoxy-2-α-phthalimidomethyl-α-D-ribofuranoside; With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 50 ℃; for 5.5h; Inert atmosphere; Reflux;

With water; sodium hydrogencarbonate; In 1,2-dichloro-ethane; at 20 ℃; diastereoselective reaction;
DOI:10.1039/c2cc34556k

Reference yield:

: 61255-42-3
C₁₉H₃₅N₅OSi₂

: 1394848-33-9
methyl 3,5-di-O-benzyl-2-deoxy-2-α-phthalimidomethyl-α-D-ribofuranoside

: 1394848-48-6
C₄₁H₄₄N₆O₆

: 1394848-47-5
N6-n-octanoyl-3',5'-di-O-benzyl-2'-deoxy-2'-C-α-phthalimidomethyladenosine

Guidance literature:: C₁₉H₃₅N₅OSi₂; methyl 3,5-di-O-benzyl-2-deoxy-2-α-phthalimidomethyl-α-D-ribofuranoside; With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; for 2h; Inert atmosphere; Reflux;

With water; sodium hydrogencarbonate; In 1,2-dichloro-ethane; at 20 ℃; optical yield given as %de;
DOI:10.1039/c2cc34556k

Reference yield:

: 885592-69-8
(2S,4R,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-methoxydihydrofuran-3(2H)-one

: 1394848-47-5
N6-n-octanoyl-3',5'-di-O-benzyl-2'-deoxy-2'-C-α-phthalimidomethyladenosine

Guidance literature:: Multi-step reaction with 4 steps

1.1: sec.-butyllithium / tetrahydrofuran; cyclohexane / 1 h / -78 °C / Inert atmosphere

1.2: 72 h / -78 - 20 °C / Inert atmosphere

2.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

2.2: 2 h / 20 °C

3.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

4.1: trimethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / 5.5 h / 50 °C / Inert atmosphere; Reflux

4.2: 20 °C

With 9-borabicyclo[3.3.1]nonane dimer; trimethylsilyl trifluoromethanesulfonate; sec.-butyllithium; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; cyclohexane; 1,2-dichloro-ethane; 1.2: Wittig reaction / 2.1: Hydroboration reaction / 3.1: Mitsunobu reaction;
DOI:10.1039/c2cc34556k