O⁶-benzyl-N²-[[[[4'-[(2'',3'',4''-tri-O-acetyl-6''-methyl-β-D-glucopyranuronosyl)oxy]-3'-nitrophenyl]methyl]oxy]carbonyl]-9-[(pivaloyloxy)methyl]guanine

Base Information

• Chemical Name: O⁶-benzyl-N²-[[[[4'-[(2'',3'',4''-tri-O-acetyl-6''-methyl-β-D-glucopyranuronosyl)oxy]-3'-nitrophenyl]methyl]oxy]carbonyl]-9-[(pivaloyloxy)methyl]guanine
• CAS No.: 832739-10-3
• Molecular Formula: C₃₉H₄₂N₆O₁₇
• Molecular Weight: 866.792

Synonyms:O⁶-benzyl-N²-[[[[4'-[(2'',3'',4''-tri-O-acetyl-6''-methyl-β-D-glucopyranuronosyl)oxy]-3'-nitrophenyl]methyl]oxy]carbonyl]-9-[(pivaloyloxy)methyl]guanine

Chemical Property of O⁶-benzyl-N²-[[[[4'-[(2'',3'',4''-tri-O-acetyl-6''-methyl-β-D-glucopyranuronosyl)oxy]-3'-nitrophenyl]methyl]oxy]carbonyl]-9-[(pivaloyloxy)methyl]guanine

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Technology Process of O⁶-benzyl-N²-[[[[4'-[(2'',3'',4''-tri-O-acetyl-6''-methyl-β-D-glucopyranuronosyl)oxy]-3'-nitrophenyl]methyl]oxy]carbonyl]-9-[(pivaloyloxy)methyl]guanine

There total 2 articles about O⁶-benzyl-N²-[[[[4'-[(2'',3'',4''-tri-O-acetyl-6''-methyl-β-D-glucopyranuronosyl)oxy]-3'-nitrophenyl]methyl]oxy]carbonyl]-9-[(pivaloyloxy)methyl]guanine 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: 42.0%

(2-amino-6-(benzyloxy)-9H-purin-9-yl)methyl pivalate (152833-02-8) + (25,3R,45,55,65)-2-(4-(hydroxymethyl)-2-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (148579-94-6) → O6-benzyl-N2-[[[[4'-[(2'',3'',4''-tri-O-acetyl-6''-methyl-β-D-glucopyranuronosyl)oxy]-3'-nitrophenyl]methyl]oxy]carbonyl]-9-[(pivaloyloxy)methyl]guanine (832739-10-3)

Guidance literature:

(2-amino-6-(benzyloxy)-9H-purin-9-yl)methyl pivalate; With pyridine; In dichloromethane; toluene; at 0 - 20 ℃; for 20h;

(2S,3R,4S,5S,6S)-2-(4-(hydroxymethyl)-2-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate; In dichloromethane; toluene; at 20 ℃; for 2h;

Reference yield: 42.0%

phosgene (75-44-5) + (2-amino-6-(benzyloxy)-9H-purin-9-yl)methyl pivalate (152833-02-8) + (25,3R,45,55,65)-2-(4-(hydroxymethyl)-2-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (148579-94-6) → O6-benzyl-N2-[[[[4'-[(2'',3'',4''-tri-O-acetyl-6''-methyl-β-D-glucopyranuronosyl)oxy]-3'-nitrophenyl]methyl]oxy]carbonyl]-9-[(pivaloyloxy)methyl]guanine (832739-10-3)

Guidance literature:

phosgene; (2-amino-6-(benzyloxy)-9H-purin-9-yl)methyl pivalate; With pyridine; In dichloromethane; toluene; for 20h;

(2S,3R,4S,5S,6S)-2-(4-(hydroxymethyl)-2-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate; In dichloromethane; toluene; at 20 ℃; for 2h;

DOI:10.1021/jm0493865

upstream raw materials:

phosgene

(2-amino-6-(benzyloxy)-9H-purin-9-yl)methyl pivalate

(25,3R,45,55,65)-2-(4-(hydroxymethyl)-2-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

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