7-(1,3-dioxan-2-yl)-heptyl 6-O-acetyl-2,3-di-O-benzyl-α-D-galactopyranoside

Base Information

• Chemical Name: 7-(1,3-dioxan-2-yl)-heptyl 6-O-acetyl-2,3-di-O-benzyl-α-D-galactopyranoside
• CAS No.: 783367-45-3
• Molecular Formula: C₃₃H₄₆O₉
• Molecular Weight: 586.723
• Mol file: 783367-45-3.mol

Synonyms:7-(1,3-dioxan-2-yl)-heptyl 6-O-acetyl-2,3-di-O-benzyl-α-D-galactopyranoside

Chemical Property of 7-(1,3-dioxan-2-yl)-heptyl 6-O-acetyl-2,3-di-O-benzyl-α-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-(1,3-dioxan-2-yl)-heptyl 6-O-acetyl-2,3-di-O-benzyl-α-D-galactopyranoside

There total 2 articles about 7-(1,3-dioxan-2-yl)-heptyl 6-O-acetyl-2,3-di-O-benzyl-α-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:

pent-4-enyl 6-O-acetyl-2,3-di-O-benzyl-β-D-galactopyranoside (613664-61-2) + 7-(1,3-dioxan-2-yl)-heptan-1-ol (783367-43-1) → 7-(1,3-dioxan-2-yl)-heptyl 6-O-acetyl-2,3-di-O-benzyl-α-D-galactopyranoside (783367-45-3)

Guidance literature:

pent-4-enyl 6-O-acetyl-2,3-di-O-benzyl-β-D-galactopyranoside; With bromine; In dichloromethane; at 0 ℃;

7-(1,3-dioxan-2-yl)-heptan-1-ol; With 4 A molecular sieve; tetraethylammonium bromide; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/j.carres.2004.06.012

Reference yield:

2-(7-(tert-butyldiphenylsilyloxy)-heptyl)-1,3-dioxane (783367-42-0) → 7-(1,3-dioxan-2-yl)-heptyl 6-O-acetyl-2,3-di-O-benzyl-α-D-galactopyranoside (783367-45-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 99 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

2.1: Br₂ / CH₂Cl₂ / 0 °C

2.2: 4 Angstroem molecular sieves; Et₄NBr / CH₂Cl₂ / 0 - 20 °C

With tetrabutyl ammonium fluoride; bromine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.carres.2004.06.012

Reference yield: 16.0%

Pent-4-enyl 6-O-acetyl-2,3-di-O-benzyl-4-O-chloroacetyl-β-D-galactopyranoside (344550-96-5) + 7-(1,3-dioxan-2-yl)-heptyl 6-O-acetyl-2,3-di-O-benzyl-α-D-galactopyranoside (783367-45-3) → Chloro-acetic acid (2R,3S,4S,5R,6R)-2-acetoxymethyl-6-[(2R,3S,4S,5R,6S)-2-acetoxymethyl-4,5-bis-benzyloxy-6-(7-[1,3]dioxan-2-yl-heptyloxy)-tetrahydro-pyran-3-yloxy]-4,5-bis-benzyloxy-tetrahydro-pyran-3-yl ester (783367-47-5)

Guidance literature:

With N-iodo-succinimide; triethylsilyl trifluoromethyl sulfonate; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1016/j.carres.2004.06.012

upstream raw materials:

pent-4-enyl 6-O-acetyl-2,3-di-O-benzyl-β-D-galactopyranoside

7-(1,3-dioxan-2-yl)-heptan-1-ol

2-(7-(tert-butyldiphenylsilyloxy)-heptyl)-1,3-dioxane

Downstream raw materials:

Chloro-acetic acid (2R,3S,4S,5R,6R)-2-acetoxymethyl-6-[(2R,3S,4S,5R,6S)-2-acetoxymethyl-4,5-bis-benzyloxy-6-(7-[1,3]dioxan-2-yl-heptyloxy)-tetrahydro-pyran-3-yloxy]-4,5-bis-benzyloxy-tetrahydro-pyran-3-yl ester

Acetic acid (2R,3S,4S,5R,6S)-3-((2R,3R,4S,5S,6R)-6-acetoxymethyl-3,4-bis-benzyloxy-5-hydroxy-tetrahydro-pyran-2-yloxy)-4,5-bis-benzyloxy-6-(7-[1,3]dioxan-2-yl-heptyloxy)-tetrahydro-pyran-2-ylmethyl ester