methyl 1-O-(4-methanesulfonyloxymethyl-2-nitrophenyl)-2,3,4-tri-O-acetyl-β-D-glucopyranuronate

Base Information

• Chemical Name: methyl 1-O-(4-methanesulfonyloxymethyl-2-nitrophenyl)-2,3,4-tri-O-acetyl-β-D-glucopyranuronate
• CAS No.: 1018932-83-6
• Molecular Formula: C₂₁H₂₅NO₁₅S
• Molecular Weight: 563.493
• Mol file: 1018932-83-6.mol

Synonyms:methyl 1-O-(4-methanesulfonyloxymethyl-2-nitrophenyl)-2,3,4-tri-O-acetyl-β-D-glucopyranuronate

Chemical Property of methyl 1-O-(4-methanesulfonyloxymethyl-2-nitrophenyl)-2,3,4-tri-O-acetyl-β-D-glucopyranuronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 1-O-(4-methanesulfonyloxymethyl-2-nitrophenyl)-2,3,4-tri-O-acetyl-β-D-glucopyranuronate

There total 5 articles about methyl 1-O-(4-methanesulfonyloxymethyl-2-nitrophenyl)-2,3,4-tri-O-acetyl-β-D-glucopyranuronate 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: 97.0%

methanesulfonyl chloride (124-63-0) + (25,3R,45,55,65)-2-(4-(hydroxymethyl)-2-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (148579-94-6) → methyl 1-O-(4-methanesulfonyloxymethyl-2-nitrophenyl)-2,3,4-tri-O-acetyl-β-D-glucopyranuronate (1018932-83-6)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/jm701151c

Reference yield:

(2S,3R,4S,5S,6S)-2-(4-formyl-2-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (148579-93-5) → methyl 1-O-(4-methanesulfonyloxymethyl-2-nitrophenyl)-2,3,4-tri-O-acetyl-β-D-glucopyranuronate (1018932-83-6)

Guidance literature:

Multi-step reaction with 2 steps

1: silica gel; sodium tetrahydroborate / isopropyl alcohol; chloroform / 1 h / 0 °C

2: triethylamine / dichloromethane / 1 h / 0 °C

With sodium tetrahydroborate; silica gel; triethylamine; In dichloromethane; chloroform; isopropyl alcohol;

Reference yield:

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester (21085-72-3) → methyl 1-O-(4-methanesulfonyloxymethyl-2-nitrophenyl)-2,3,4-tri-O-acetyl-β-D-glucopyranuronate (1018932-83-6)

Guidance literature:

Multi-step reaction with 3 steps

1: silver(l) oxide / acetonitrile / 4 h / 20 °C

2: silica gel; sodium tetrahydroborate / isopropyl alcohol; chloroform / 1 h / 0 °C

3: triethylamine / dichloromethane / 1 h / 0 °C

With sodium tetrahydroborate; silica gel; triethylamine; silver(l) oxide; In dichloromethane; chloroform; isopropyl alcohol; acetonitrile;

upstream raw materials:

methanesulfonyl chloride

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

(2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

D-glucurono-6,3-lactone

Downstream raw materials:

10-[4-(2,3,4-tri-O-acetyl-6-O-methyl-β-D-glucuronyloxy)-3-nitrobenzyloxy]camptothecin

10-[4-O-(methyl-2,3,4-tri-O-acetyl-β-D-glucopyranuronate)-3-nitrobenzyloxy]-5,6-dihydro-4H-benzo[de]quinoline-camptothecin