1′,5′-anhydro-2′-(N(6)-benzoyl-adenin-9-yl)-2′,3′-dideoxy-6′-O-monomethoxytrityl-D-ribohexitol

Base Information

Chemical Name:1′,5′-anhydro-2′-(N(6)-benzoyl-adenin-9-yl)-2′,3′-dideoxy-6′-O-monomethoxytrityl-D-ribohexitol
CAS No.:383859-49-2
Molecular Formula:C₃₈H₃₅N₅O₅
Molecular Weight:641.726
Hs Code.:

Synonyms:1′,5′-anhydro-2′-(N(6)-benzoyl-adenin-9-yl)-2′,3′-dideoxy-6′-O-monomethoxytrityl-D-ribohexitol

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Chemical Property of 1′,5′-anhydro-2′-(N(6)-benzoyl-adenin-9-yl)-2′,3′-dideoxy-6′-O-monomethoxytrityl-D-ribohexitol

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Technology Process of 1′,5′-anhydro-2′-(N(6)-benzoyl-adenin-9-yl)-2′,3′-dideoxy-6′-O-monomethoxytrityl-D-ribohexitol

There total 19 articles about 1′,5′-anhydro-2′-(N(6)-benzoyl-adenin-9-yl)-2′,3′-dideoxy-6′-O-monomethoxytrityl-D-ribohexitol 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: 85.0%

: 14470-28-1
mono-4-methoxytrityl chloride

: 383859-48-1
3′-deoxy-2′-(N(6)-benzoyladenin-9-yl)-1′,5′-anhydro-D-ribo-hexitol

: 383859-49-2
1′,5′-anhydro-2′-(N(6)-benzoyl-adenin-9-yl)-2′,3′-dideoxy-6′-O-monomethoxytrityl-D-ribohexitol

Guidance literature:: With pyridine; at 20 ℃; for 3h; Inert atmosphere;
DOI:10.1021/acs.joc.5b00406

Reference yield:

: 152613-20-2
(4aR,7R,8aS)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-ol

: 383859-49-2
1′,5′-anhydro-2′-(N(6)-benzoyl-adenin-9-yl)-2′,3′-dideoxy-6′-O-monomethoxytrityl-D-ribohexitol

Guidance literature:: Multi-step reaction with 9 steps

1.1: DEAD; triphenylphosphine / tetrahydrofuran

2.1: 4 g / NH₃ / methanol

3.1: pyridine / 72 h / 20 °C

4.1: 2.36 g / aq. AcOH / 5 h / 80 °C

5.1: 84 percent / pyridine / 20 °C

6.1: LiH; 12-crown-4 / dimethylformamide / 1 h / 90 °C

6.2: 23 percent / dimethylformamide / 60 °C

7.1: 55 percent / aq. NaOH / dioxane / 24 h / 60 °C

8.1: 80 percent / trimethylsilylchloride; pyridine / 0 °C

9.1: 75 percent / pyridine / 60 h / 20 °C

With pyridine; sodium hydroxide; chloro-trimethyl-silane; (1,4,7,10-tetraoxacyclododecane); ammonia; lithium hydride; acetic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; methanol; N,N-dimethyl-formamide; 1.1: Mitsunobu reaction;
DOI:10.1021/ol016183r

Reference yield:

: 383859-43-6
(4aR,7S,8aS)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-ol

: 383859-49-2
1′,5′-anhydro-2′-(N(6)-benzoyl-adenin-9-yl)-2′,3′-dideoxy-6′-O-monomethoxytrityl-D-ribohexitol

Guidance literature:: Multi-step reaction with 7 steps

1.1: pyridine / 72 h / 20 °C

2.1: 2.36 g / aq. AcOH / 5 h / 80 °C

3.1: 84 percent / pyridine / 20 °C

4.1: LiH; 12-crown-4 / dimethylformamide / 1 h / 90 °C

4.2: 23 percent / dimethylformamide / 60 °C

5.1: 55 percent / aq. NaOH / dioxane / 24 h / 60 °C

6.1: 80 percent / trimethylsilylchloride; pyridine / 0 °C

7.1: 75 percent / pyridine / 60 h / 20 °C

With pyridine; sodium hydroxide; chloro-trimethyl-silane; (1,4,7,10-tetraoxacyclododecane); lithium hydride; acetic acid; In 1,4-dioxane; N,N-dimethyl-formamide;
DOI:10.1021/ol016183r