(2S,3R,4E)-2-azido-3-(benzoyloxy)-1-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)oxy]-4-octadecene

Base Information

• Chemical Name: (2S,3R,4E)-2-azido-3-(benzoyloxy)-1-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)oxy]-4-octadecene
• CAS No.: 118711-43-6
• Molecular Formula: C₃₉H₅₇N₃O₁₂
• Molecular Weight: 759.894

Synonyms:(2S,3R,4E)-2-azido-3-(benzoyloxy)-1-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)oxy]-4-octadecene

Chemical Property of (2S,3R,4E)-2-azido-3-(benzoyloxy)-1-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)oxy]-4-octadecene

Chemical Property:

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Technology Process of (2S,3R,4E)-2-azido-3-(benzoyloxy)-1-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)oxy]-4-octadecene

There total 2 articles about (2S,3R,4E)-2-azido-3-(benzoyloxy)-1-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)oxy]-4-octadecene 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%

(2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol (103348-50-1) + 2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate (86520-63-0) → (2S,3R,4E)-2-azido-3-(benzoyloxy)-1-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)oxy]-4-octadecene (118711-43-6)

Guidance literature:

With 4 A molecular sieve; tin(IV) chloride; In hexane; dichloromethane; for 1h;

DOI:10.1021/jm9606960

Reference yield: 9.5%

(2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol (103348-50-1) + 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) → (2S,3R,4E)-2-azido-3-(benzoyloxy)-1-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)oxy]-4-octadecene (118711-43-6) + (2S,3R,4E)-2-azido-3-(benzoyloxy)-1-[(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)oxy]-4-octadecene

Guidance literature:

With mercury(II) cyanide; In nitromethane; at 80 - 85 ℃; for 0.333333h;

DOI:10.1021/jm9606960

Reference yield: 89.0%

(2S,3R,4E)-2-azido-3-(benzoyloxy)-1-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)oxy]-4-octadecene (118711-43-6) → (2S,3R,4E)-2-azido-3-(benzoyloxy)-1-(β-D-galactopyranosyloxy)-4-octadecene (172340-47-5)

Guidance literature:

With sodium methylate; In methanol; dichloromethane; at -70 - -50 ℃; for 3h;

DOI:10.1021/jm9606960

upstream raw materials:

(2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol

2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

Downstream raw materials:

(2S,3R,4E)-2-azido-3-(benzoyloxy)-1-(β-D-galactopyranosyloxy)-4-octadecene

Benzoic acid (E)-(R)-1-[(S)-1-amino-2-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-ethyl]-hexadec-2-enyl ester

(2S,3R,4E)-2-azido-1-[(4,6-O-benzylidene-β-D-galactopyranosyl)oxy]-4-octadecene

(2S,3R,4E)-2-azido-3-(benzoyloxy)-1-[(3,4-O-isopropylidene-β-D-galactopyranosyl)oxy]-4-octadecene

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