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

Base Information

• Chemical Name: N-[(2R,4aR,6R,7R,8R,8aS)-6-Benzyloxy-8-hydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide
• CAS No.: 139893-41-7
• Molecular Formula: C₂₃H₂₇NO₇
• Molecular Weight: 429.47
• Mol file: 139893-41-7.mol

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

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

There total 4 articles about N-[(2R,4aR,6R,7R,8R,8aS)-6-Benzyloxy-8-hydroxy-2-(4-methoxy-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: 77.0%

p-Anisaldehyde dimethyl acetal (2186-92-7) + benzyl 2-acetamido-2-deoxy-β-D-glucopyranoside (3055-51-4,3554-93-6,10380-86-6,13343-62-9,13343-67-4,19374-70-0,33423-30-2,33501-36-9,41355-95-7,86834-14-2,111003-11-3,347411-88-5) → N-[(2R,4aR,6R,7R,8R,8aS)-6-Benzyloxy-8-hydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide (139893-41-7)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1002/(sici)1099-0690(199910)1999:10<2523::aid-ejoc2523>3.0.co;2-q

Reference yield:

2-deoxy-2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranose (10294-12-9,10353-11-4,70749-28-9,76612-22-1,116559-73-0,147129-68-8,34051-43-9) → N-[(2R,4aR,6R,7R,8R,8aS)-6-Benzyloxy-8-hydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide (139893-41-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 65 percent / NaH / CH₂Cl₂ / 10 h / 20 °C

2: 90 percent / MeONa / methanol

3: 77 percent / TsOH / dimethylformamide

With sodium methylate; sodium hydride; toluene-4-sulfonic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; 1: Benzylation / 2: Methanolyis / 3: Condensation;

DOI:10.1002/(sici)1099-0690(199910)1999:10<2523::aid-ejoc2523>3.0.co;2-q

Reference yield:

benzyl bromide (100-39-0) → N-[(2R,4aR,6R,7R,8R,8aS)-6-Benzyloxy-8-hydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide (139893-41-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 65 percent / NaH / CH₂Cl₂ / 10 h / 20 °C

2: 90 percent / MeONa / methanol

3: 77 percent / TsOH / dimethylformamide

With sodium methylate; sodium hydride; toluene-4-sulfonic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; 1: Benzylation / 2: Methanolyis / 3: Condensation;

DOI:10.1002/(sici)1099-0690(199910)1999:10<2523::aid-ejoc2523>3.0.co;2-q

upstream raw materials:

p-Anisaldehyde dimethyl acetal

benzyl 2-acetamido-2-deoxy-β-D-glucopyranoside

2-deoxy-2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranose

benzyl bromide

Downstream raw materials:

Acetic acid (2S,3R,4S,5R,6R)-2-[(2R,3R,4R,6R)-3-acetylamino-2-benzyloxy-6-(4-methoxy-benzyloxymethyl)-5-oxo-tetrahydro-pyran-4-yloxy]-4,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-yl ester

Acetic acid (2R,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6R)-3-acetylamino-2-benzyloxy-5-hydroxy-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-4-yloxy]-4,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-yl ester

Acetic acid (2R,3R,4S,5R,6R)-2-[(2R,3R,4R,5S,6R)-3-acetylamino-2-benzyloxy-5-hydroxy-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-4-yloxy]-4,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-yl ester

Acetic acid (2R,3R,4S,5R,6R)-2-((2R,3R,4R,5S,6R)-3-acetylamino-2-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-4,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-yl ester