Benzyl-carbamic acid (1R,2R,4R,5R)-4-(6-amino-purin-9-yl)-3,6-dioxa-bicyclo[3.1.0]hex-2-ylmethyl ester

Base Information

• Chemical Name: Benzyl-carbamic acid (1R,2R,4R,5R)-4-(6-amino-purin-9-yl)-3,6-dioxa-bicyclo[3.1.0]hex-2-ylmethyl ester
• CAS No.: 182126-72-3
• Molecular Formula: C₁₈H₁₈N₆O₄
• Molecular Weight: 382.379
• Mol file: 182126-72-3.mol

Synonyms:Benzyl-carbamic acid (1R,2R,4R,5R)-4-(6-amino-purin-9-yl)-3,6-dioxa-bicyclo[3.1.0]hex-2-ylmethyl ester

Chemical Property of Benzyl-carbamic acid (1R,2R,4R,5R)-4-(6-amino-purin-9-yl)-3,6-dioxa-bicyclo[3.1.0]hex-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzyl-carbamic acid (1R,2R,4R,5R)-4-(6-amino-purin-9-yl)-3,6-dioxa-bicyclo[3.1.0]hex-2-ylmethyl ester

There total 1 articles about Benzyl-carbamic acid (1R,2R,4R,5R)-4-(6-amino-purin-9-yl)-3,6-dioxa-bicyclo[3.1.0]hex-2-ylmethyl 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:

9-(2,3-anhydro-β-D-ribofuranosyl)adenine (2627-64-7) + acetone O-<(vinyloxy)carbonyl>oxime (139705-38-7) + benzylamine (100-46-9) → Benzyl-carbamic acid (1R,2R,4R,5R)-4-(6-amino-purin-9-yl)-3,6-dioxa-bicyclo[3.1.0]hex-2-ylmethyl ester (182126-72-3)

Guidance literature:

Yield given. Multistep reaction; 1.) lipase from C_. antarctica, THF, 60 deg C, 24 h, 2.) THF, reflux, 8 h;

DOI:10.1021/jo9606259

Reference yield: 88.0%

Benzyl-carbamic acid (1R,2R,4R,5R)-4-(6-amino-purin-9-yl)-3,6-dioxa-bicyclo[3.1.0]hex-2-ylmethyl ester (182126-72-3) → (4aS,6R,7R,7aR)-6-(6-Amino-purin-9-yl)-1-benzyl-7-hydroxy-hexahydro-furo[3,2-d][1,3]oxazin-2-one (182126-75-6)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 100 - 110 ℃; for 0.166667h;

DOI:10.1021/jo9606259

Reference yield:

Benzyl-carbamic acid (1R,2R,4R,5R)-4-(6-amino-purin-9-yl)-3,6-dioxa-bicyclo[3.1.0]hex-2-ylmethyl ester (182126-72-3) → (2R,3R,4R,5S)-2-(6-Amino-purin-9-yl)-4-benzylamino-5-hydroxymethyl-tetrahydro-furan-3-ol (134934-82-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / NaH / dimethylformamide / 0.17 h / 100 - 110 °C

2: 75 percent / LiOH / aq. ethanol / Heating

With lithium hydroxide; sodium hydride; In ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jo9606259

upstream raw materials:

9-(2,3-anhydro-β-D-ribofuranosyl)adenine

acetone O-<(vinyloxy)carbonyl>oxime

benzylamine

Downstream raw materials:

(4aS,6R,7R,7aR)-6-(6-Amino-purin-9-yl)-1-benzyl-7-hydroxy-hexahydro-furo[3,2-d][1,3]oxazin-2-one

(2R,3R,4R,5S)-2-(6-Amino-purin-9-yl)-4-benzylamino-5-hydroxymethyl-tetrahydro-furan-3-ol