2-(8-aza-O⁶-benzylguan-9-yl)ethyl-β-D-tetra-O-acetylglucoside

Base Information

• Chemical Name: 2-(8-aza-O⁶-benzylguan-9-yl)ethyl-β-D-tetra-O-acetylglucoside
• CAS No.: 382607-84-3
• Molecular Formula: C₂₇H₃₂N₆O₁₁
• Molecular Weight: 616.585
• Mol file: 382607-84-3.mol

Synonyms:2-(8-aza-O⁶-benzylguan-9-yl)ethyl-β-D-tetra-O-acetylglucoside

Chemical Property of 2-(8-aza-O⁶-benzylguan-9-yl)ethyl-β-D-tetra-O-acetylglucoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(8-aza-O⁶-benzylguan-9-yl)ethyl-β-D-tetra-O-acetylglucoside

There total 3 articles about 2-(8-aza-O⁶-benzylguan-9-yl)ethyl-β-D-tetra-O-acetylglucoside 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: 19.8%

7-(benzyloxy)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-amine (6301-83-3) + 2-bromoethyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (16977-78-9,85193-55-1,86651-32-3,86651-40-3) → 2-(8-aza-O6-benzylguan-9-yl)ethyl-β-D-tetra-O-acetylglucoside (382607-84-3)

Guidance literature:

7-(benzyloxy)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-amine; With lithium hydride; In N,N-dimethyl-formamide; at 20 - 80 ℃; for 1h;

2-bromoethyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside; In N,N-dimethyl-formamide; Further stages.; Heating;

DOI:10.1021/jm010006e

Reference yield:

2,4,5-triamino-6-benzyloxy-pyrimidine (19916-72-4) → 2-(8-aza-O6-benzylguan-9-yl)ethyl-β-D-tetra-O-acetylglucoside (382607-84-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 63 percent / sodium nitrite; acetic acid / acetone / 2 h

2.1: LiH / dimethylformamide / 1 h / 20 - 80 °C

2.2: 19.8 percent / dimethylformamide / Heating

With lithium hydride; acetic acid; sodium nitrite; In N,N-dimethyl-formamide; acetone;

DOI:10.1021/jm010006e

Reference yield:

β-D-glucose pentaacetate (604-69-3) → 2-(8-aza-O6-benzylguan-9-yl)ethyl-β-D-tetra-O-acetylglucoside (382607-84-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 36.1 percent / 4 Angstroem molecular sieves; trimethylsilyl triflate / CH₂Cl₂

2.1: LiH / dimethylformamide / 1 h / 20 - 80 °C

2.2: 19.8 percent / dimethylformamide / Heating

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; lithium hydride; In dichloromethane; N,N-dimethyl-formamide; 1.1: Koenigs-Knorr reaction;

DOI:10.1021/jm010006e

upstream raw materials:

7-(benzyloxy)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-amine

2-bromoethyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

2,4,5-triamino-6-benzyloxy-pyrimidine

β-D-glucose pentaacetate