{(2R,3R,4S,5S,6R)-2-[(4aR,6S,7R,8R,8aR)-7-Acetylamino-6-methoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy}-acetic acid methyl ester

Base Information

• Chemical Name: {(2R,3R,4S,5S,6R)-2-[(4aR,6S,7R,8R,8aR)-7-Acetylamino-6-methoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy}-acetic acid methyl ester
• CAS No.: 316139-76-1
• Molecular Formula: C₂₆H₃₇NO₁₄
• Molecular Weight: 587.578

Synonyms:{(2R,3R,4S,5S,6R)-2-[(4aR,6S,7R,8R,8aR)-7-Acetylamino-6-methoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy}-acetic acid methyl ester

Chemical Property of {(2R,3R,4S,5S,6R)-2-[(4aR,6S,7R,8R,8aR)-7-Acetylamino-6-methoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy}-acetic acid methyl ester

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Technology Process of {(2R,3R,4S,5S,6R)-2-[(4aR,6S,7R,8R,8aR)-7-Acetylamino-6-methoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy}-acetic acid methyl ester

There total 5 articles about {(2R,3R,4S,5S,6R)-2-[(4aR,6S,7R,8R,8aR)-7-Acetylamino-6-methoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy}-acetic acid methyl ester 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: 57.0%

bromoacetic acid methyl ester (96-32-2) + N-[(4aR,6S,7R,8R,8aR)-6-Methoxy-2-(4-methoxy-phenyl)-8-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide (316139-75-0) → {(2R,3R,4S,5S,6R)-2-[(4aR,6S,7R,8R,8aR)-7-Acetylamino-6-methoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy}-acetic acid methyl ester (316139-76-1)

Guidance literature:

N-[(4aR,6S,7R,8R,8aR)-6-Methoxy-2-(4-methoxy-phenyl)-8-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide; With di(n-butyl)tin oxide; In methanol; for 3h; Heating;

bromoacetic acid methyl ester; With tetra-(n-butyl)ammonium iodide; at 60 - 65 ℃; for 48h;

DOI:10.1016/S0960-894X(00)00497-2

Reference yield:

p-Anisaldehyde dimethyl acetal (2186-92-7) → {(2R,3R,4S,5S,6R)-2-[(4aR,6S,7R,8R,8aR)-7-Acetylamino-6-methoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy}-acetic acid methyl ester (316139-76-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 75 percent / PTS / acetonitrile / 12 h / 20 °C

2.1: 65 percent / Hg(CN)2 / benzene; nitromethane / 12 h / 40 - 45 °C

3.1: 94 percent / 1 M aq. NaOMe / methanol; CH₂Cl₂ / 2 h / 20 °C / pH 10.0

4.1: n-Bu₂SnO / methanol / 3 h / Heating

4.2: 57 percent / n-Bu₄NI / 48 h / 60 - 65 °C

With sodium methylate; mercury(II) cyanide; pyridinium p-toluenesulfonate; di(n-butyl)tin oxide; In methanol; nitromethane; dichloromethane; acetonitrile; benzene; 1.1: acetalization / 2.1: glycosylation / 3.1: Deacetylation / 4.1: Metallation;

DOI:10.1016/S0960-894X(00)00497-2

Reference yield:

methyl α-D-N-acetylgalactosamine (6082-22-0) → {(2R,3R,4S,5S,6R)-2-[(4aR,6S,7R,8R,8aR)-7-Acetylamino-6-methoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy}-acetic acid methyl ester (316139-76-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 75 percent / PTS / acetonitrile / 12 h / 20 °C

2.1: 65 percent / Hg(CN)2 / benzene; nitromethane / 12 h / 40 - 45 °C

3.1: 94 percent / 1 M aq. NaOMe / methanol; CH₂Cl₂ / 2 h / 20 °C / pH 10.0

4.1: n-Bu₂SnO / methanol / 3 h / Heating

4.2: 57 percent / n-Bu₄NI / 48 h / 60 - 65 °C

With sodium methylate; mercury(II) cyanide; pyridinium p-toluenesulfonate; di(n-butyl)tin oxide; In methanol; nitromethane; dichloromethane; acetonitrile; benzene; 1.1: acetalization / 2.1: glycosylation / 3.1: Deacetylation / 4.1: Metallation;

DOI:10.1016/S0960-894X(00)00497-2

upstream raw materials:

bromoacetic acid methyl ester

N-[(4aR,6S,7R,8R,8aR)-6-Methoxy-2-(4-methoxy-phenyl)-8-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

p-Anisaldehyde dimethyl acetal

methyl α-D-N-acetylgalactosamine

Downstream raw materials:

Chloro-acetic acid (2R,3R,4S,5S,6R)-2-[(4aR,6S,7R,8R,8aR)-7-acetylamino-6-methoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-5-(2-chloro-acetoxy)-6-(2-chloro-acetoxymethyl)-4-methoxycarbonylmethoxy-tetrahydro-pyran-3-yl ester

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