8-methoxycarbonyloctyl O-(6-O-benzoyl-3,4-isopropylidene-β-D-galactopyranosyl)-(1->4)-2-azido-6-O-benzoyl-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: 8-methoxycarbonyloctyl O-(6-O-benzoyl-3,4-isopropylidene-β-D-galactopyranosyl)-(1->4)-2-azido-6-O-benzoyl-2-deoxy-β-D-glucopyranoside
• CAS No.: 858640-97-8
• Molecular Formula: C₃₉H₅₁N₃O₁₄
• Molecular Weight: 785.846
• Mol file: 858640-97-8.mol

Synonyms:8-methoxycarbonyloctyl O-(6-O-benzoyl-3,4-isopropylidene-β-D-galactopyranosyl)-(1->4)-2-azido-6-O-benzoyl-2-deoxy-β-D-glucopyranoside

Chemical Property of 8-methoxycarbonyloctyl O-(6-O-benzoyl-3,4-isopropylidene-β-D-galactopyranosyl)-(1->4)-2-azido-6-O-benzoyl-2-deoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8-methoxycarbonyloctyl O-(6-O-benzoyl-3,4-isopropylidene-β-D-galactopyranosyl)-(1->4)-2-azido-6-O-benzoyl-2-deoxy-β-D-glucopyranoside

There total 4 articles about 8-methoxycarbonyloctyl O-(6-O-benzoyl-3,4-isopropylidene-β-D-galactopyranosyl)-(1->4)-2-azido-6-O-benzoyl-2-deoxy-β-D-glucopyranoside 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:

9-[(2R,3R,4R,5S,6R)-3-Azido-4-hydroxy-6-hydroxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester (148225-89-2) → 8-methoxycarbonyloctyl O-(6-O-benzoyl-3,4-isopropylidene-β-D-galactopyranosyl)-(1->4)-2-azido-6-O-benzoyl-2-deoxy-β-D-glucopyranoside (858640-97-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 146 mg / FeCl₃ / 0.5 h / Heating

2: 71 percent / Rt₃N / dimethylformamide / 1 h / -40 °C

With iron(III) chloride; In N,N-dimethyl-formamide;

DOI:10.1002/chem.200400831

Reference yield:

8-methoxycarbonyloctyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-acetyl-2-azido-2-deoxy-β-D-glucopyranoside (148225-85-8) → 8-methoxycarbonyloctyl O-(6-O-benzoyl-3,4-isopropylidene-β-D-galactopyranosyl)-(1->4)-2-azido-6-O-benzoyl-2-deoxy-β-D-glucopyranoside (858640-97-8)

Guidance literature:

Multi-step reaction with 3 steps

1: MeONa / methanol / 20 °C

2: 146 mg / FeCl₃ / 0.5 h / Heating

3: 71 percent / Rt₃N / dimethylformamide / 1 h / -40 °C

With sodium methylate; iron(III) chloride; In methanol; N,N-dimethyl-formamide;

DOI:10.1002/chem.200400831

Reference yield:

methyl 9-hydroxynonanoate (34957-73-8) → 8-methoxycarbonyloctyl O-(6-O-benzoyl-3,4-isopropylidene-β-D-galactopyranosyl)-(1->4)-2-azido-6-O-benzoyl-2-deoxy-β-D-glucopyranoside (858640-97-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 33 percent / BF₃*OEt₂; 4 Angstroem molecular sieves / CH₂Cl₂; hexane / 0.5 h / -40 °C

2: MeONa / methanol / 20 °C

3: 146 mg / FeCl₃ / 0.5 h / Heating

4: 71 percent / Rt₃N / dimethylformamide / 1 h / -40 °C

With 4 A molecular sieve; boron trifluoride diethyl etherate; sodium methylate; iron(III) chloride; In methanol; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/chem.200400831

upstream raw materials:

9-[(2R,3R,4R,5S,6R)-3-Azido-4-hydroxy-6-hydroxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester

8-methoxycarbonyloctyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-acetyl-2-azido-2-deoxy-β-D-glucopyranoside

methyl 9-hydroxynonanoate

(2S,3R,4S,5S,6R)-2-(((2R,3S,4R,5R,6R)-4-acetoxy-2-(acetoxymethyl)-5-azido-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3-yl)oxy)-6-(acetoxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Downstream raw materials:

C₅₁H₆₇N₃O₂₀S