(1'R,2'R,3'R,4'R)-9-(4-benzyloxy-3-benzyloxymethyl-2-hydroxycyclopentyl)adenine

Base Information

• Chemical Name: (1'R,2'R,3'R,4'R)-9-(4-benzyloxy-3-benzyloxymethyl-2-hydroxycyclopentyl)adenine
• CAS No.: 263764-12-1
• Molecular Formula: C₂₅H₂₇N₅O₃
• Molecular Weight: 445.521
• Mol file: 263764-12-1.mol

Synonyms:(1'R,2'R,3'R,4'R)-9-(4-benzyloxy-3-benzyloxymethyl-2-hydroxycyclopentyl)adenine

Chemical Property of (1'R,2'R,3'R,4'R)-9-(4-benzyloxy-3-benzyloxymethyl-2-hydroxycyclopentyl)adenine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1'R,2'R,3'R,4'R)-9-(4-benzyloxy-3-benzyloxymethyl-2-hydroxycyclopentyl)adenine

There total 1 articles about (1'R,2'R,3'R,4'R)-9-(4-benzyloxy-3-benzyloxymethyl-2-hydroxycyclopentyl)adenine 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: 73.7%

sodium adeninate (40428-86-2,52287-61-3,52994-56-6) + (1R,2S,3R,5S)-3-Benzyloxy-2-benzyloxymethyl-6-oxa-bicyclo[3.1.0]hexane (873298-16-9) → (1'R,2'R,3'R,4'R)-9-(4-benzyloxy-3-benzyloxymethyl-2-hydroxycyclopentyl)adenine (263764-12-1)

Guidance literature:

In N,N-dimethyl-formamide; at 140 ℃; for 27h;

DOI:10.1039/b312276j

Reference yield: 78.3%

(1'R,2'R,3'R,4'R)-9-(4-benzyloxy-3-benzyloxymethyl-2-hydroxycyclopentyl)adenine (263764-12-1) → (1'R,2'R,3'R,4'R)-9-(4-benzyloxy-3-benzyloxymethyl-2-hydroxycyclopentyl)-8-bromoadenine

Guidance literature:

With bromine; sodium acetate; In 1,4-dioxane; at 20 ℃; for 10h; pH=5.0;

DOI:10.1039/b312276j

Reference yield:

(1'R,2'R,3'R,4'R)-9-(4-benzyloxy-3-benzyloxymethyl-2-hydroxycyclopentyl)adenine (263764-12-1) → (6'aS,7'S,8'R,9'aR)-2-(4-tert-butylphenoxy)-N-(7',8',9',9'a-tetrahydro-8'-hydroxy-7'-hydroxymethyl-6'aH-cyclopenta[4,5]oxazolo[3,2-e]purin-4'-yl)acetamide (670275-99-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 78.3 percent / Br₂; aq. sodium acetate / dioxane / 10 h / 20 °C / pH 5.0

2.1: 96.7 percent / DMAP / CH₂Cl₂ / 20 °C

3.1: sodium acetate; Ac₂O / acetic acid / Heating

3.2: 74.3 percent / NH₃ / methanol / 7 h / 60 °C

4.1: 86.6 percent / pyridine / 1.5 h / 20 °C

5.1: 74.1 percent / cyclohexene / Pd(OH)2/C / dimethylformamide / 2 h / 90 °C

With pyridine; dmap; bromine; sodium acetate; acetic anhydride; cyclohexene; palladium dihydroxide; In 1,4-dioxane; dichloromethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1039/b312276j

upstream raw materials:

sodium adeninate

(1R,2S,3R,5S)-3-Benzyloxy-2-benzyloxymethyl-6-oxa-bicyclo[3.1.0]hexane

Downstream raw materials:

(6aS,7S,8R,9aR)-8-benzyloxy-7-benzyloxymethyl-7,8,9,9a-tetrahydro-6aH-cyclopenta[4,5]oxazolo[3,2-e]purin-4-amine

(6'aS,7'S,8'R,9'aR)-2-(4-tert-butylphenoxy)-N-(7',8',9',9'a-tetrahydro-8'-hydroxy-7'-hydroxymethyl-6'aH-cyclopenta[4,5]oxazolo[3,2-e]purin-4'-yl)acetamide

(6'aS,7'S,8'R,9'aR)-N-(8'-benzyloxy-7'-benzyloxymethyl-7',8',9',9'a-tetrahydro-6'aH-cyclopenta[4,5]oxazolo[3,2-e]purin-4'-yl)-2-(4-tert-butylphenoxy)acetamide

(6'aS,7'S,8'R,9'aR)-2-(4-tert-butylphenoxy)-N-[7'-(4,4'-dimethoxytrityloxymethyl)-7',8',9',9'a-tetrahydro-8'-hydroxy-7'-hydroxymethyl-6'aH-cyclopenta[4,5]oxazolo[3,2-e]purin-4'-yl]acetamide