4-Methoxyphenyl 3-O-Benzyl-beta-D-galactopyranoside

Base Information

• Chemical Name: 4-Methoxyphenyl 3-O-Benzyl-beta-D-galactopyranoside
• CAS No.: 383905-60-0
• Molecular Formula: C20H24 O7
• Molecular Weight: 376.4
• DSSTox Substance ID: DTXSID60693679
• Wikidata: Q82622689
• Mol file: 383905-60-0.mol

Synonyms:4-Methoxyphenyl 3-O-Benzyl-beta-D-galactopyranoside;383905-60-0;(2S,3S,4S,5S,6S)-2-(hydroxymethyl)-6-(4-methoxyphenoxy)-4-phenylmethoxyoxane-3,5-diol;DTXSID60693679;MFCD11112174;M1725;4-Methoxyphenyl 3-O-benzyl-alpha-L-allopyranoside

Chemical Property of 4-Methoxyphenyl 3-O-Benzyl-beta-D-galactopyranoside

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 154 °C
• Refractive Index: 1.613
• Boiling Point: 599.163°C at 760 mmHg
• Flash Point: 316.163°C
• PSA: 97.61000
• Density: 1.337g/cm³
• LogP: 1.09840
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 376.15220310
• Heavy Atom Count: 27
• Complexity: 421

Purity/Quality:

97% ^*data from raw suppliers

4-Methoxyphenyl 3-O-benzyl-b-D-galactopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)OC2C(C(C(C(O2)CO)O)OCC3=CC=CC=C3)O
• Isomeric SMILES: COC1=CC=C(C=C1)O[C@H]2[C@H]([C@H]([C@H]([C@@H](O2)CO)O)OCC3=CC=CC=C3)O

Technology Process of 4-Methoxyphenyl 3-O-Benzyl-beta-D-galactopyranoside

There total 4 articles about 4-Methoxyphenyl 3-O-Benzyl-beta-D-galactopyranoside 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: 87.0%

benzyl bromide (100-39-0) + 4-methoxyphenyl β-D-galactopyranoside (3150-20-7,6032-32-2,28541-75-5,85481-53-4,89731-58-8,109121-56-4,121468-39-1,12167-34-9) → p-methoxyphenyl 3-O-benzyl-β-D-galactopyranoside (383905-60-0)

Guidance literature:

4-methoxyphenyl β-D-galactopyranoside; With di(n-butyl)tin oxide; In toluene; for 17h; Heating;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In toluene; for 2h; Heating;

DOI:10.1016/S0008-6215(01)00194-X

Reference yield:

4-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (2872-65-3,14581-81-8,17042-40-9,84380-06-3,105260-62-6) → p-methoxyphenyl 3-O-benzyl-β-D-galactopyranoside (383905-60-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaOCH₃ / methanol / 2 h

2.1: dibutyltin oxide / toluene / 17 h / Heating

2.2: 87 percent / tetrabutylammonium iodide / toluene / 2 h / Heating

With sodium methylate; di(n-butyl)tin oxide; In methanol; toluene;

DOI:10.1016/S0008-6215(01)00194-X

Reference yield:

β-D-galactose peracetate (4163-60-4) → p-methoxyphenyl 3-O-benzyl-β-D-galactopyranoside (383905-60-0)

Guidance literature:

Multi-step reaction with 3 steps

1: methanesulfonic acid / neat (no solvent) / 90 - 100 °C

2: sodium methoxide / methanol / 3 h / 70 °C

3: tetrabutylammonium bromide; di-n-butyltin(IV) oxide / neat (no solvent) / 3 h / 70 °C / Alkaline conditions

With methanesulfonic acid; tetrabutylammonium bromide; sodium methoxide; di-n-butyltin(IV) oxide; In methanol;

DOI:10.3390/ijms23052581

upstream raw materials:

benzyl bromide

4-methoxyphenyl β-D-galactopyranoside

4-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside

β-D-galactose peracetate

Downstream raw materials:

p-methoxyphenyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-galactopyranoside

4-methoxyphenyl 2,4,6-tri-O-acetyl-β-D-galactopyranoside

p-methoxyphenyl 2,4,6-tri-O-acetyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranoside

3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2,4,6-tri-O-acetyl-α-D-galactopyranosyl trichloroacetimidate

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