5-[O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)oxymethyl]-5-{N-[(4-methylthiobenzyl)carboximido]}-2,2-dimethyl-1,3-dioxane

Base Information

• Chemical Name: 5-[O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)oxymethyl]-5-{N-[(4-methylthiobenzyl)carboximido]}-2,2-dimethyl-1,3-dioxane
• CAS No.: 1400872-58-3
• Molecular Formula: C₃₀H₄₁NO₁₃S
• Molecular Weight: 655.72
• Mol file: 1400872-58-3.mol

Synonyms:

Chemical Property of 5-[O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)oxymethyl]-5-{N-[(4-methylthiobenzyl)carboximido]}-2,2-dimethyl-1,3-dioxane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-[O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)oxymethyl]-5-{N-[(4-methylthiobenzyl)carboximido]}-2,2-dimethyl-1,3-dioxane

There total 3 articles about 5-[O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)oxymethyl]-5-{N-[(4-methylthiobenzyl)carboximido]}-2,2-dimethyl-1,3-dioxane 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: 76.0%

2-(4-(methylthio)phenyl)acetic acid (16188-55-9) + 5-[O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)oxymethyl]-5-amino-2,2-dimethyl-1,3-dioxane (1400872-56-1) → 5-[O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)oxymethyl]-5-{N-[(4-methylthiobenzyl)carboximido]}-2,2-dimethyl-1,3-dioxane (1400872-58-3)

Guidance literature:

With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 24h; Inert atmosphere;

DOI:10.1080/07328303.2011.654017

Reference yield:

5-[O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)oxymethyl]-5-(N-benzyloxycarbonyl)-2,2-dimethyl-1,3-dioxane (1400872-55-0) → 5-[O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)oxymethyl]-5-{N-[(4-methylthiobenzyl)carboximido]}-2,2-dimethyl-1,3-dioxane (1400872-58-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 10% Pd/C; hydrogen / ethanol / 5 h / 3102.97 Torr

2: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 24 h / Inert atmosphere

With 10% Pd/C; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In ethanol; N,N-dimethyl-formamide;

DOI:10.1080/07328303.2011.654017

Reference yield:

(5-benzyloxycarbonylamino-2,2-dimethyl[1,3]dioxan-5-yl)methanol (420107-80-8) → 5-[O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)oxymethyl]-5-{N-[(4-methylthiobenzyl)carboximido]}-2,2-dimethyl-1,3-dioxane (1400872-58-3)

Guidance literature:

Multi-step reaction with 3 steps

1: mercury(II) cyanide / acetonitrile / 20 °C / Inert atmosphere

2: 10% Pd/C; hydrogen / ethanol / 5 h / 3102.97 Torr

3: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 24 h / Inert atmosphere

With 10% Pd/C; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; mercury(II) cyanide; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In ethanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1080/07328303.2011.654017

upstream raw materials:

2-(4-(methylthio)phenyl)acetic acid

5-[O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)oxymethyl]-5-amino-2,2-dimethyl-1,3-dioxane

(5-benzyloxycarbonylamino-2,2-dimethyl[1,3]dioxan-5-yl)methanol

5-[O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)oxymethyl]-5-(N-benzyloxycarbonyl)-2,2-dimethyl-1,3-dioxane