N-[(2R,4aR,6S,7R,8R,8aS)-6-((2S,3S,4R,5R,6S)-3,5-Bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

Base Information

• Chemical Name: N-[(2R,4aR,6S,7R,8R,8aS)-6-((2S,3S,4R,5R,6S)-3,5-Bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide
• CAS No.: 184048-02-0
• Molecular Formula: C₃₆H₄₃NO₁₀
• Molecular Weight: 649.738
• Mol file: 184048-02-0.mol

Synonyms:N-[(2R,4aR,6S,7R,8R,8aS)-6-((2S,3S,4R,5R,6S)-3,5-Bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

Chemical Property of N-[(2R,4aR,6S,7R,8R,8aS)-6-((2S,3S,4R,5R,6S)-3,5-Bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(2R,4aR,6S,7R,8R,8aS)-6-((2S,3S,4R,5R,6S)-3,5-Bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

There total 6 articles about N-[(2R,4aR,6S,7R,8R,8aS)-6-((2S,3S,4R,5R,6S)-3,5-Bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-8-hydroxy-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: 86.0%

benzaldehyde dimethyl acetal (1125-88-8) + Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-((2S,3S,4R,5R,6S)-3,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-tetrahydro-pyran-4-yl ester → N-[(2R,4aR,6S,7R,8R,8aS)-6-((2S,3S,4R,5R,6S)-3,5-Bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide (184048-02-0)

Guidance literature:

With camphor-10-sulfonic acid; In N,N-dimethyl-formamide; for 5h; Ambient temperature;

DOI:10.1080/07328309608005702

Reference yield:

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranosyl bromide (70831-94-6) → N-[(2R,4aR,6S,7R,8R,8aS)-6-((2S,3S,4R,5R,6S)-3,5-Bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide (184048-02-0)

Guidance literature:

Multi-step reaction with 4 steps

1: AgOTf, MS 4A, 2,4,6-trimethylpyridine / 1.) CH₂Cl₂, r.t., 0.5 h, 2.) -40 deg C, 2 h; r.t., 8 h

2: N₂H₄*H₂O / ethanol / 6 h / Heating

3: pyridine / 8 h / Ambient temperature

4: 86 percent / camphorsulfonic acid / dimethylformamide / 5 h / Ambient temperature

With pyridine; 2,4,6-trimethyl-pyridine; camphor-10-sulfonic acid; silver trifluoromethanesulfonate; hydrazine hydrate; In ethanol; N,N-dimethyl-formamide;

DOI:10.1080/07328309608005702

Reference yield:

Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-amino-6-((2S,3S,4R,5R,6S)-3,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-tetrahydro-pyran-4-yl ester → N-[(2R,4aR,6S,7R,8R,8aS)-6-((2S,3S,4R,5R,6S)-3,5-Bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide (184048-02-0)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 8 h / Ambient temperature

2: 86 percent / camphorsulfonic acid / dimethylformamide / 5 h / Ambient temperature

With pyridine; camphor-10-sulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1080/07328309608005702

upstream raw materials:

benzaldehyde dimethyl acetal

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranosyl bromide

Methyl 2,4-di-O-benzyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-β-L-fucopyranoside

Methyl 2,4-di-O-benzyl-β-L-fucopyranoside