beta-d-Galactopyranoside, methyl, 2,4,6-triacetate

Base Information

• Chemical Name: beta-d-Galactopyranoside, methyl, 2,4,6-triacetate
• CAS No.: 19464-78-9
• Molecular Formula: C₁₃H₂₀O₉
• Molecular Weight: 320.296
• DSSTox Substance ID: DTXSID701244414
• Nikkaji Number: J924.913C
• Mol file: 19464-78-9.mol

Synonyms:19464-78-9;beta-d-galactopyranoside, methyl, 2,4,6-triacetate;DTXSID701244414;(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-4-hydroxy-6-methoxytetrahydro-2H-pyran-3,5-diyl diacetate

Chemical Property of beta-d-Galactopyranoside, methyl, 2,4,6-triacetate

Chemical Property:

• XLogP3: 0
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 8
• Exact Mass: 320.11073221
• Heavy Atom Count: 22
• Complexity: 422

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)OC)OC(=O)C)O)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)OC)OC(=O)C)O)OC(=O)C

Technology Process of beta-d-Galactopyranoside, methyl, 2,4,6-triacetate

There total 1 articles about beta-d-Galactopyranoside, methyl, 2,4,6-triacetate 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: 25.0%

methyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (5019-23-8) → methyl 2,4-di-O-acetyl-β-D-galactopyranoside + methyl 2,3,4-tri-O-acetyl-β-D-galactopyranoside (38982-58-0) + methyl 2,4,6-tri-O-acetyl-β-D-galactopyranoside (19464-78-9) + methyl beta-D-galactopyranoside (1824-94-8)

Guidance literature:

With Neisseria sicca SB cellulose acetate esterase; In phosphate buffer; at 20 ℃; for 1.5h; pH=7.0; Further Variations:; time; Product distribution;

DOI:10.1271/bbb.69.1292

Reference yield: 55.0%

benzyl bromide (100-39-0) + methyl 2,4,6-tri-O-acetyl-β-D-galactopyranoside (19464-78-9) → methyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-galactopyranoside (81348-24-5)

Guidance literature:

With silver carbonate; In toluene; at 60 ℃; for 18h; Darkness;

DOI:10.1016/j.carres.2009.12.012

Reference yield:

methyl 2,4,6-tri-O-acetyl-β-D-galactopyranoside (19464-78-9) → ammonium O-(1-O-methyl-β-D-galactopyranos-3-yl) ((4-acetamidophenyl)methyl)phosphonate

Guidance literature:

Multi-step reaction with 5 steps

1: tetrazole / CH₂Cl₂ / 20 °C

2: 84 percent / aq. HCl / dioxane; CH₂Cl₂

3: 23 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 24 h / 20 °C

4: hydrogen / Pd/C / methanol / 2 h

5: aq. ammonia / dioxane / 20 °C

With 1H-tetrazole; hydrogenchloride; ammonium hydroxide; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal; In 1,4-dioxane; methanol; dichloromethane;

DOI:10.1080/07328300701351532

upstream raw materials:

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

Downstream raw materials:

O-benzyl O-(1-O-methyl-2,4,6-tri-O-acetyl-β-D-galactopyranos-3-yl)phosphonic acid

dibenzyl O-(1-O-methyl-2,4,6-tri-O-acetyl-β-D-galactopyranos-3-yl)phosphate

O-benzyl O-(1-O-methyl-2,4,6-tri-O-acetyl-β-D-galactopyranos-3-yl) ((4-acetamidophenyl)(hydroxy)methyl)phosphonate

O-benzyl O-(1-O-methyl-2,4,6-tri-O-acetyl-β-D-galactopyranos-3-yl) (phenylmethyl)phosphonate