4-carboxymethyl-2-nitrobenzyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside

Base Information

• Chemical Name: 4-carboxymethyl-2-nitrobenzyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
• CAS No.: 142386-71-8
• Molecular Formula: C₄₇H₅₉NO₃₀
• Molecular Weight: 1117.97
• Mol file: 142386-71-8.mol

Synonyms:

Chemical Property of 4-carboxymethyl-2-nitrobenzyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-carboxymethyl-2-nitrobenzyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside

There total 2 articles about 4-carboxymethyl-2-nitrobenzyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 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: 28.0%

methyl 4-(hydroxymethyl)-3-nitrobenzoate (89950-93-6) + Acetic acid (3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-bromo-5-[(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-4-yl ester → 4-carboxymethyl-2-nitrobenzyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside (142386-71-8)

Guidance literature:

With 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; Ambient temperature;

DOI:10.1016/S0008-6215(00)90563-9

Reference yield:

O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-acetyl-α-D-glucopyranosyl)-(1->4)-1,2,3,6-tetra-O-acetyl-α,β-D-glucopyranose (63425-89-8,63492-73-9,63492-74-0,63640-29-9,68108-21-4,142435-88-9,142435-89-0) → 4-carboxymethyl-2-nitrobenzyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside (142386-71-8)

Guidance literature:

Multi-step reaction with 2 steps

1: HBr / CH₂Cl₂ / 0.75 h

2: 28 percent / molecular sieves 4 Angstroem, silver triflate / CH₂Cl₂ / Ambient temperature

With 4 A molecular sieve; hydrogen bromide; silver trifluoromethanesulfonate; In dichloromethane;

DOI:10.1016/S0008-6215(00)90563-9

Reference yield:

4-carboxymethyl-2-nitrobenzyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside (142386-71-8) → 4-carboxy-2-nitrobenzyl O-α-D-glucopyranosyl-(1->6)-O-α-D-glucopyranosyl-(1->4)-β-D-glucopyranoside (142386-72-9)

Guidance literature:

With methanol; sodium hydroxide; sodium methylate; Yield given. Multistep reaction; 1.) methanol, 30 min, 2.) water, 20 min;

DOI:10.1016/S0008-6215(00)90563-9

upstream raw materials:

methyl 4-(hydroxymethyl)-3-nitrobenzoate

O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-acetyl-α-D-glucopyranosyl)-(1->4)-1,2,3,6-tetra-O-acetyl-α,β-D-glucopyranose

Downstream raw materials:

4-carboxy-2-nitrobenzyl O-α-D-glucopyranosyl-(1->6)-O-α-D-glucopyranosyl-(1->4)-β-D-glucopyranoside