methyl N-[9-(β-D-glucuronyl)benzyloxycarbonyl]aminocamptothecin

Base Information

• Chemical Name: methyl N-[9-(β-D-glucuronyl)benzyloxycarbonyl]aminocamptothecin
• CAS No.: 246032-59-7
• Molecular Formula: C₃₅H₃₃N₃O₁₃
• Molecular Weight: 703.659
• Mol file: 246032-59-7.mol

Synonyms:methyl N-[9-(β-D-glucuronyl)benzyloxycarbonyl]aminocamptothecin

Chemical Property of methyl N-[9-(β-D-glucuronyl)benzyloxycarbonyl]aminocamptothecin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl N-[9-(β-D-glucuronyl)benzyloxycarbonyl]aminocamptothecin

There total 8 articles about methyl N-[9-(β-D-glucuronyl)benzyloxycarbonyl]aminocamptothecin 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:

methyl 1-(4-hydroxymethylphenyl)-β-D-glucopyranuronate (246032-58-6) + (4-ethyl-4-hydroxy-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-10-yl)-carbamic acid 4-nitro-phenyl ester → methyl N-[9-(β-D-glucuronyl)benzyloxycarbonyl]aminocamptothecin (246032-59-7)

Guidance literature:

With dmap; In acetonitrile; at 80 ℃; for 2h;

DOI:10.1021/jm990124q

Reference yield:

2,3,4-tri-O-acetyl-1-bromo-1-deoxy-β-D-glucopyranuronic acid methy ester (6919-98-8) → methyl N-[9-(β-D-glucuronyl)benzyloxycarbonyl]aminocamptothecin (246032-59-7)

Guidance literature:

Multi-step reaction with 4 steps

1: Ag₂O / acetonitrile / 2 h / 20 °C

2: 90 percent / NaBH₄ / propan-2-ol; CHCl₃ / 1 h / 0 °C

3: 60.2 percent / CH₃ONa / methanol / 2 h / 20 °C

4: DMAP / acetonitrile / 2 h / 80 °C

With dmap; sodium tetrahydroborate; sodium methylate; silver(l) oxide; In methanol; chloroform; isopropyl alcohol; acetonitrile; 1: Addition / 2: Reduction / 3: Deacetylation / 4: Substitution;

DOI:10.1021/jm990124q

Reference yield:

methyl D-glucopyranuronate (82228-14-6) → methyl N-[9-(β-D-glucuronyl)benzyloxycarbonyl]aminocamptothecin (246032-59-7)

Guidance literature:

Multi-step reaction with 6 steps

1: HClO₄ / 24 h / 20 °C

2: TiBr₄ / CH₂Cl₂ / 24 h / 20 °C

3: Ag₂O / acetonitrile / 2 h / 20 °C

4: 90 percent / NaBH₄ / propan-2-ol; CHCl₃ / 1 h / 0 °C

5: 60.2 percent / CH₃ONa / methanol / 2 h / 20 °C

6: DMAP / acetonitrile / 2 h / 80 °C

With dmap; sodium tetrahydroborate; perchloric acid; sodium methylate; titanium(IV) bromide; silver(l) oxide; In methanol; dichloromethane; chloroform; isopropyl alcohol; acetonitrile; 1: Acetylation / 2: Bromination / 3: Addition / 4: Reduction / 5: Deacetylation / 6: Substitution;

DOI:10.1021/jm990124q

upstream raw materials:

methyl 1-(4-hydroxymethylphenyl)-β-D-glucopyranuronate

2,3,4-tri-O-acetyl-1-bromo-1-deoxy-β-D-glucopyranuronic acid methy ester

methyl D-glucopyranuronate

9-amino-20(S)-camptothecin