N-{(2S,3R,4R,5R,6R)-2-Allyloxy-4-[(3aS,4R,6R,7R,7aR)-4-(tert-butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-5-hydroxy-6-methoxymethyl-tetrahydro-pyran-3-yl}-acetamide

Base Information

• Chemical Name: N-{(2S,3R,4R,5R,6R)-2-Allyloxy-4-[(3aS,4R,6R,7R,7aR)-4-(tert-butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-5-hydroxy-6-methoxymethyl-tetrahydro-pyran-3-yl}-acetamide
• CAS No.: 172842-46-5
• Molecular Formula: C₃₇H₅₃NO₁₁Si
• Molecular Weight: 715.913

Synonyms:

Chemical Property of N-{(2S,3R,4R,5R,6R)-2-Allyloxy-4-[(3aS,4R,6R,7R,7aR)-4-(tert-butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-5-hydroxy-6-methoxymethyl-tetrahydro-pyran-3-yl}-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-{(2S,3R,4R,5R,6R)-2-Allyloxy-4-[(3aS,4R,6R,7R,7aR)-4-(tert-butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-5-hydroxy-6-methoxymethyl-tetrahydro-pyran-3-yl}-acetamide

There total 7 articles about N-{(2S,3R,4R,5R,6R)-2-Allyloxy-4-[(3aS,4R,6R,7R,7aR)-4-(tert-butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-5-hydroxy-6-methoxymethyl-tetrahydro-pyran-3-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:

N-((2S,3R,4R,5R,6R)-2-Allyloxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-acetamide (64650-83-5) → N-{(2S,3R,4R,5R,6R)-2-Allyloxy-4-[(3aS,4R,6R,7R,7aR)-4-(tert-butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-5-hydroxy-6-methoxymethyl-tetrahydro-pyran-3-yl}-acetamide (172842-46-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 77 percent / 4-toluenesulfonic acid monohydrate / dimethylformamide / 16 h / Ambient temperature

2: Hg(CN)2 / benzene; nitromethane / 16 h / 55 °C

3: 70percent aq. acetic acid / 1 h / 70 °C

4: 69 percent / 2,6-di-(tert-butyl)-4-methylpyridine / CH₂Cl₂ / 5 h / Ambient temperature

5: 69 percent / NaOMe / methanol / 16 h / Ambient temperature

6: 93 percent / imidazole / dimethylformamide / 2 h / 0 °C

7: 4-toluenesulfonic acid monohydrate / acetone / 1 h / Ambient temperature

With 1H-imidazole; 2,6-di-tert-butyl-4-methylpyridine; p-toluenesulfonic acid monohydrate; sodium methylate; mercury(II) cyanide; acetic acid; In methanol; nitromethane; dichloromethane; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1016/0008-6215(95)00162-M

Reference yield:

allyl 2-acetamido-2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-galactopyranoside (172926-90-8) → N-{(2S,3R,4R,5R,6R)-2-Allyloxy-4-[(3aS,4R,6R,7R,7aR)-4-(tert-butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-5-hydroxy-6-methoxymethyl-tetrahydro-pyran-3-yl}-acetamide (172842-46-5)

Guidance literature:

Multi-step reaction with 6 steps

1: Hg(CN)2 / benzene; nitromethane / 16 h / 55 °C

2: 70percent aq. acetic acid / 1 h / 70 °C

3: 69 percent / 2,6-di-(tert-butyl)-4-methylpyridine / CH₂Cl₂ / 5 h / Ambient temperature

4: 69 percent / NaOMe / methanol / 16 h / Ambient temperature

5: 93 percent / imidazole / dimethylformamide / 2 h / 0 °C

6: 4-toluenesulfonic acid monohydrate / acetone / 1 h / Ambient temperature

With 1H-imidazole; 2,6-di-tert-butyl-4-methylpyridine; p-toluenesulfonic acid monohydrate; sodium methylate; mercury(II) cyanide; acetic acid; In methanol; nitromethane; dichloromethane; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1016/0008-6215(95)00162-M

Reference yield:

allyl O-(β-D-galactopyranosyl)-(1<*>3)-2-acetamido-2-deoxy-6-O-methyl-α-D-galactopyranoside (172842-44-3) → N-{(2S,3R,4R,5R,6R)-2-Allyloxy-4-[(3aS,4R,6R,7R,7aR)-4-(tert-butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-5-hydroxy-6-methoxymethyl-tetrahydro-pyran-3-yl}-acetamide (172842-46-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / imidazole / dimethylformamide / 2 h / 0 °C

2: 4-toluenesulfonic acid monohydrate / acetone / 1 h / Ambient temperature

With 1H-imidazole; p-toluenesulfonic acid monohydrate; In N,N-dimethyl-formamide; acetone;

DOI:10.1016/0008-6215(95)00162-M

upstream raw materials:

2,2-dimethoxy-propane

allyl O-(6-O-tert-butyldiphenylsilyl-β-D-galactopyranosyl)-(1<*>3)-2-acetamido-2-deoxy-6-O-methyl-α-D-galactopyranoside

N-((2S,3R,4R,5R,6R)-2-Allyloxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-acetamide

allyl 2-acetamido-2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-galactopyranoside

Downstream raw materials:

allyl O-(2-O-acetyl-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1<*>3)-2-acetamido-4-O-acetyl-2-deoxy-6-O-methyl-α-D-galactopyranoside

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