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

Base Information

• Chemical Name: 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
• CAS No.: 172842-47-6
• Molecular Formula: C₄₁H₅₇NO₁₃Si
• Molecular Weight: 799.988
• Mol file: 172842-47-6.mol

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 8 articles about 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 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) → 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 (172842-47-6)

Guidance literature:

Multi-step reaction with 8 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

8: pyridine, N,N-dimethyl-4-aminopyridine / 16 h

With pyridine; 1H-imidazole; dmap; 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) → 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 (172842-47-6)

Guidance literature:

Multi-step reaction with 7 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

7: pyridine, N,N-dimethyl-4-aminopyridine / 16 h

With pyridine; 1H-imidazole; dmap; 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) → 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 (172842-47-6)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: pyridine, N,N-dimethyl-4-aminopyridine / 16 h

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

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

upstream raw materials:

acetic anhydride

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

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