4-Nitrophenyl3-O-(a-D-glucopyranosyl)-a-D-glucopyranoside

Base Information

• Chemical Name: 4-Nitrophenyl3-O-(a-D-glucopyranosyl)-a-D-glucopyranoside
• CAS No.: 136632-95-6
• Molecular Formula: C₁₈H₂₅NO₁₃
• Molecular Weight: 463.395
• Mol file: 136632-95-6.mol

Synonyms:4-Nitrophenyl |A-Nigeroside;4-Nitrophenyl 3-O-|A-D-Glucopyranosyl-|A-D-glucopyranoside;W0361;

Chemical Property of 4-Nitrophenyl3-O-(a-D-glucopyranosyl)-a-D-glucopyranoside

Chemical Property:

• Melting Point: 188-190°C
• Boiling Point: 814.5±65.0 °C(Predicted)
• PKA: 12.34±0.70(Predicted)
• PSA: 224.35000
• Density: 1.70±0.1 g/cm3(Predicted)
• LogP: -2.87910

Purity/Quality:

98%Min ^*data from raw suppliers

4-Nitrophenyl3-O-α-D-Glucopyranosyl-α-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-Nitrophenyl 3-O-α-D-Glucopyranosyl-α-D-glucopyranoside (cas# 136632-95-6) is a compound useful in organic synthesis.

Technology Process of 4-Nitrophenyl3-O-(a-D-glucopyranosyl)-a-D-glucopyranoside

There total 13 articles about 4-Nitrophenyl3-O-(a-D-glucopyranosyl)-a-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: 82.0%

p-nitrophenyl 2,4,6-tri-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside (105600-45-1) → p-nitrophenyl 3-O-α-D-mannopyranosyl-α-D-mannopyranoside (26255-70-9,81562-04-1,81573-30-0,86021-56-9,110891-71-9,136632-95-6,147103-37-5,150301-00-1,93979-06-7)

Guidance literature:

With sodium methylate; In methanol; for 1h;

DOI:10.1016/S0008-6215(00)90315-X

Reference yield: 13.0%

Maltose + 4-nitrophenyl-α-D-glucopyranoside (3767-28-0) → p-nitrophenyl-α-D-glucopyranosyl-(1→4)-O-α-D-glucopyranoside (3482-57-3,4419-94-7,7344-00-5,17400-77-0,56846-39-0,78248-67-6,80446-81-7) + (2R,3R,4S,5S,6R)-2-[(2R,3R,4S,5R,6R)-3,5-Dihydroxy-2-hydroxymethyl-6-(4-nitro-phenoxy)-tetrahydro-pyran-4-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (136632-95-6) + 4-nitrophenyl α-isomaltoside (72647-96-2,80321-98-8,104872-92-6,107870-85-9,131348-49-7,143615-14-9,144939-65-1,145772-76-5,136734-56-0,335193-88-9)

Guidance literature:

In water; at 37 ℃; for 12h; biosynthesis by rice α-glucosidase (0.05 M acetate buffer pH 5.0);

DOI:10.1016/0008-6215(91)84137-4

Reference yield:

p-nitrophenyl 4,6-O-benzylidene-α-D-mannopyranoside (58056-41-0) → p-nitrophenyl 3-O-α-D-mannopyranosyl-α-D-mannopyranoside (26255-70-9,81562-04-1,81573-30-0,86021-56-9,110891-71-9,136632-95-6,147103-37-5,150301-00-1,93979-06-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 60 percent / p-toluenesulfonic acid / dimethylformamide / 48 h / Ambient temperature

2: 61 percent / silver triflate, 2,4,6-collidine / toluene; nitromethane / 0.25 h / -25 °C

3: 1.) 90 percent aqu. acetic acid, 2.) 0.2 M sodium methoxide / 1.) reflux, 30 min, 2.) methanol, 3 h, room temperature

With 2,4,6-trimethyl-pyridine; sodium methylate; silver trifluoromethanesulfonate; acetic acid; toluene-4-sulfonic acid; In nitromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/0008-6215(84)85024-7

upstream raw materials:

4-nitrophenyl-α-D-glucopyranoside

p-nitrophenyl 2,4,6-tri-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside

p-nitrophenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-α-D-mannopyranoside

2,3,4,6-Tetra-O-benzoyl-α-D-mannopyranosyl bromide

Downstream raw materials:

C₄₄H₅₅NO₂₈

C₄₄H₅₅NO₂₈

C₂₄H₃₅NO₁₈

C₂₄H₃₅NO₁₈