(4aR,6R,7R,8R,8aR)-2-Phenyl-6-(2-tetradecyl-hexadecyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

Base Information

• Chemical Name: (4aR,6R,7R,8R,8aR)-2-Phenyl-6-(2-tetradecyl-hexadecyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol
• CAS No.: 196204-50-9
• Molecular Formula: C₄₃H₇₆O₆
• Molecular Weight: 689.073
• Mol file: 196204-50-9.mol

Synonyms:(4aR,6R,7R,8R,8aR)-2-Phenyl-6-(2-tetradecyl-hexadecyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

Chemical Property of (4aR,6R,7R,8R,8aR)-2-Phenyl-6-(2-tetradecyl-hexadecyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aR,6R,7R,8R,8aR)-2-Phenyl-6-(2-tetradecyl-hexadecyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

There total 1 articles about (4aR,6R,7R,8R,8aR)-2-Phenyl-6-(2-tetradecyl-hexadecyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 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: 78.0%

benzaldehyde dimethyl acetal (1125-88-8) + 2-(tetradecyl)hexadecyl β-D-galactopyranoside (171733-54-3) → (4aR,6R,7R,8R,8aR)-2-Phenyl-6-(2-tetradecyl-hexadecyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol (196204-50-9)

Guidance literature:

With (1S)-10-camphorsulfonic acid; In N,N-dimethyl-formamide; at 45 ℃; for 0.75h;

DOI:10.1271/bbb.61.1615

Reference yield: 93.0%

levulinic anhydride (40608-06-8) + (4aR,6R,7R,8R,8aR)-2-Phenyl-6-(2-tetradecyl-hexadecyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol (196204-50-9) → 4-Oxo-pentanoic acid (4aR,6R,7R,8R,8aS)-7-hydroxy-2-phenyl-6-(2-tetradecyl-hexadecyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (196204-51-0)

Guidance literature:

With dmap; In pyridine; at -50 ℃; for 1h;

DOI:10.1271/bbb.61.1615

Reference yield:

(4aR,6R,7R,8R,8aR)-2-Phenyl-6-(2-tetradecyl-hexadecyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol (196204-50-9) → 4-Oxo-pentanoic acid (4aR,6R,7R,8S,8aS)-2-phenyl-6-(2-tetradecyl-hexadecyloxy)-7-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (196204-52-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / DMAP / pyridine / 1 h / -50 °C

2: 89 percent / N-iodosiccinimide, MesOH, 4A MS / toluene / 1 h / -20 °C

With dmap; N-iodo-succinimide; methanesulfonic acid; In pyridine; toluene;

DOI:10.1271/bbb.61.1615

upstream raw materials:

benzaldehyde dimethyl acetal

2-(tetradecyl)hexadecyl β-D-galactopyranoside

Downstream raw materials:

4-Oxo-pentanoic acid (4aR,6R,7R,8R,8aS)-7-hydroxy-2-phenyl-6-(2-tetradecyl-hexadecyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

(4aR,6R,7R,8R,8aS)-8-(4-Methoxy-benzyloxy)-2-phenyl-6-(2-tetradecyl-hexadecyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

(4aR,6R,7R,8S,8aR)-7-((2S,3S,4R,5S,6S)-3,5-Bis-benzyloxy-4-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-phenyl-6-(2-tetradecyl-hexadecyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

(4aR,6R,7R,8S,8aR)-2-Phenyl-6-(2-tetradecyl-hexadecyloxy)-7-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol