N-((4aR,6S,7R,8R,8aS)-8-Hydroxy-6-octyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide

Base Information

• Chemical Name: N-((4aR,6S,7R,8R,8aS)-8-Hydroxy-6-octyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide
• CAS No.: 215302-00-4
• Molecular Formula: C₂₃H₃₅NO₆
• Molecular Weight: 421.534

Synonyms:N-((4aR,6S,7R,8R,8aS)-8-Hydroxy-6-octyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide

Chemical Property of N-((4aR,6S,7R,8R,8aS)-8-Hydroxy-6-octyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of N-((4aR,6S,7R,8R,8aS)-8-Hydroxy-6-octyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide

There total 3 articles about N-((4aR,6S,7R,8R,8aS)-8-Hydroxy-6-octyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide 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: 73.0%

benzaldehyde dimethyl acetal (1125-88-8) + octyl 2-N-acetyl-2-amino-2-deoxy-α-D-glucopyranoside (147126-57-6,383417-49-0) → N-((4aR,6S,7R,8R,8aS)-8-Hydroxy-6-octyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide (215302-00-4)

Guidance literature:

With toluene-4-sulfonic acid; In acetonitrile; for 3h; Ambient temperature;

DOI:10.1021/jm980365i

Reference yield:

octanol (111-87-5) → N-((4aR,6S,7R,8R,8aS)-8-Hydroxy-6-octyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide (215302-00-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 35 percent / BF₃*Et₂O / acetonitrile / 18 h / Heating

2: 73 percent / p-toluenesulfonic acid / acetonitrile / 3 h / Ambient temperature

With boron trifluoride diethyl etherate; toluene-4-sulfonic acid; In acetonitrile;

DOI:10.1021/jm980365i

Reference yield:

N-Acetyl-D-glucosamine (7512-17-6,72-87-7,1136-42-1,1136-44-3,6082-29-7,6730-06-9,7772-94-3,10036-64-3,14131-60-3,14131-64-7,14131-68-1,14215-68-0,62057-49-2,62057-50-5,62057-51-6,62057-52-7,62057-53-8,62057-54-9,62057-55-0,62057-56-1,62075-50-7,62137-54-6,134451-97-1,134522-12-6,148347-16-4) → N-((4aR,6S,7R,8R,8aS)-8-Hydroxy-6-octyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide (215302-00-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 35 percent / BF₃*Et₂O / acetonitrile / 18 h / Heating

2: 73 percent / p-toluenesulfonic acid / acetonitrile / 3 h / Ambient temperature

With boron trifluoride diethyl etherate; toluene-4-sulfonic acid; In acetonitrile;

DOI:10.1021/jm980365i

upstream raw materials:

benzaldehyde dimethyl acetal

octyl 2-N-acetyl-2-amino-2-deoxy-α-D-glucopyranoside

octanol

N-Acetyl-D-glucosamine

Downstream raw materials:

N-[(2S,3R,4R,5S,6R)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxymethyl)-2-octyloxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide

N-[(2S,3R,4R,5S,6R)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxymethyl)-5-hydroxy-2-octyloxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide

N-[(2S,3R,4R,5S,6R)-5-Hydroxy-6-hydroxymethyl-2-octyloxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide

octyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)-O-[(2,3,4,6-tetra-O-benzoyl)-β-D-galactopyranosyl-(1->6)]-2-acetamido-2-deoxy-α-D-glucopyranoside

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