2,2-Dimethyl-propionic acid (2R,4S,5R)-2-(2-amino-6-chloro-purin-9-yl)-4,6-bis-benzyloxy-5-(2,2-dimethyl-propionyloxy)-hexyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (2R,4S,5R)-2-(2-amino-6-chloro-purin-9-yl)-4,6-bis-benzyloxy-5-(2,2-dimethyl-propionyloxy)-hexyl ester
• CAS No.: 183959-27-5
• Molecular Formula: C₃₅H₄₄ClN₅O₆
• Molecular Weight: 666.217
• Mol file: 183959-27-5.mol

Synonyms:2,2-Dimethyl-propionic acid (2R,4S,5R)-2-(2-amino-6-chloro-purin-9-yl)-4,6-bis-benzyloxy-5-(2,2-dimethyl-propionyloxy)-hexyl ester

Chemical Property of 2,2-Dimethyl-propionic acid (2R,4S,5R)-2-(2-amino-6-chloro-purin-9-yl)-4,6-bis-benzyloxy-5-(2,2-dimethyl-propionyloxy)-hexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (2R,4S,5R)-2-(2-amino-6-chloro-purin-9-yl)-4,6-bis-benzyloxy-5-(2,2-dimethyl-propionyloxy)-hexyl ester

There total 5 articles about 2,2-Dimethyl-propionic acid (2R,4S,5R)-2-(2-amino-6-chloro-purin-9-yl)-4,6-bis-benzyloxy-5-(2,2-dimethyl-propionyloxy)-hexyl ester 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: 71.0%

2-Amino-6-chloropurin (10310-21-1) + 2,2-Dimethyl-propionic acid (1R,2S,4R)-2-benzyloxy-1-benzyloxymethyl-5-(2,2-dimethyl-propionyloxy)-4-hydroxy-pentyl ester (183959-12-8) → 2,2-Dimethyl-propionic acid (2R,4S,5R)-2-(2-amino-6-chloro-purin-9-yl)-4,6-bis-benzyloxy-5-(2,2-dimethyl-propionyloxy)-hexyl ester (183959-27-5)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In 1,4-dioxane; Ambient temperature;

DOI:10.1016/0040-4020(96)00818-6

Reference yield:

pivaloyl chloride (3282-30-2) → 2,2-Dimethyl-propionic acid (2R,4S,5R)-2-(2-amino-6-chloro-purin-9-yl)-4,6-bis-benzyloxy-5-(2,2-dimethyl-propionyloxy)-hexyl ester (183959-27-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / pyridine / Ambient temperature

2: 63 percent / AD-mix-α, water / 2-methyl-propan-2-ol / 1.) ) deg C, 6 h, 2.) RT, overnight

3: 93 percent / pyridine / 2 h / 0 °C

4: 71 percent / Ph₃P, DEAD / dioxane / Ambient temperature

With pyridine; AD-mix-α; water; triphenylphosphine; diethylazodicarboxylate; In 1,4-dioxane; tert-butyl alcohol;

DOI:10.1016/0040-4020(96)00818-6

Reference yield:

(2R,3S)-1,3-O-dibenzyl-2-hydroxy-5-hexene (116444-15-6) → 2,2-Dimethyl-propionic acid (2R,4S,5R)-2-(2-amino-6-chloro-purin-9-yl)-4,6-bis-benzyloxy-5-(2,2-dimethyl-propionyloxy)-hexyl ester (183959-27-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / pyridine / Ambient temperature

2: 63 percent / AD-mix-α, water / 2-methyl-propan-2-ol / 1.) ) deg C, 6 h, 2.) RT, overnight

3: 93 percent / pyridine / 2 h / 0 °C

4: 71 percent / Ph₃P, DEAD / dioxane / Ambient temperature

With pyridine; AD-mix-α; water; triphenylphosphine; diethylazodicarboxylate; In 1,4-dioxane; tert-butyl alcohol;

DOI:10.1016/0040-4020(96)00818-6

upstream raw materials:

2-Amino-6-chloropurin

2,2-Dimethyl-propionic acid (1R,2S,4R)-2-benzyloxy-1-benzyloxymethyl-5-(2,2-dimethyl-propionyloxy)-4-hydroxy-pentyl ester

pivaloyl chloride

(2R,3S)-1,3-O-dibenzyl-2-hydroxy-5-hexene

Downstream raw materials:

9-(4,6-di-O-benzyl-2,3-dideoxy-2-D-mannityl)guanine

2,2-Dimethyl-propionic acid (2R,4S,5R)-2-(2-amino-6-hydroxy-purin-9-yl)-4,6-bis-benzyloxy-5-(2,2-dimethyl-propionyloxy)-hexyl ester