(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

Base Information

• Chemical Name: (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
• CAS No.: 670275-98-6
• Molecular Formula: C₃₇H₃₉N₅O₅
• Molecular Weight: 633.747
• Mol file: 670275-98-6.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 5 articles about (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 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: 86.6%

(4-tert-butylphenoxy)acetyl chloride (90734-55-7) + (6aS,7S,8R,9aR)-8-benzyloxy-7-benzyloxymethyl-7,8,9,9a-tetrahydro-6aH-cyclopenta[4,5]oxazolo[3,2-e]purin-4-amine (670275-97-5) → (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 (670275-98-6)

Guidance literature:

With pyridine; at 20 ℃; for 1.5h;

DOI:10.1039/b312276j

Reference yield:

(1R,2S,3R,5S)-3-Benzyloxy-2-benzyloxymethyl-6-oxa-bicyclo[3.1.0]hexane (873298-16-9) → (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 (670275-98-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 73.7 percent / dimethylformamide / 27 h / 140 °C

2.1: 78.3 percent / Br₂; aq. sodium acetate / dioxane / 10 h / 20 °C / pH 5.0

3.1: 96.7 percent / DMAP / CH₂Cl₂ / 20 °C

4.1: sodium acetate; Ac₂O / acetic acid / Heating

4.2: 74.3 percent / NH₃ / methanol / 7 h / 60 °C

5.1: 86.6 percent / pyridine / 1.5 h / 20 °C

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

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)-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 (670275-98-6)

Guidance literature:

Multi-step reaction with 4 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

With pyridine; dmap; bromine; sodium acetate; acetic anhydride; In 1,4-dioxane; dichloromethane; acetic acid;

DOI:10.1039/b312276j

upstream raw materials:

(4-tert-butylphenoxy)acetyl chloride

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

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

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

Downstream raw materials:

(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

(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