methyl (methyl 5-acetamido-8,9-di-O-acetyl-4-O-benzoyl-3,5,7-trideoxy-2-thio-D-galacto-2-nonulopyranosid)onate

Base Information

• Chemical Name: methyl (methyl 5-acetamido-8,9-di-O-acetyl-4-O-benzoyl-3,5,7-trideoxy-2-thio-D-galacto-2-nonulopyranosid)onate
• CAS No.: 147906-99-8
• Molecular Formula: C₂₄H₃₁NO₁₀S
• Molecular Weight: 525.577

Synonyms:methyl (methyl 5-acetamido-8,9-di-O-acetyl-4-O-benzoyl-3,5,7-trideoxy-2-thio-D-galacto-2-nonulopyranosid)onate

Chemical Property of methyl (methyl 5-acetamido-8,9-di-O-acetyl-4-O-benzoyl-3,5,7-trideoxy-2-thio-D-galacto-2-nonulopyranosid)onate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of methyl (methyl 5-acetamido-8,9-di-O-acetyl-4-O-benzoyl-3,5,7-trideoxy-2-thio-D-galacto-2-nonulopyranosid)onate

There total 9 articles about methyl (methyl 5-acetamido-8,9-di-O-acetyl-4-O-benzoyl-3,5,7-trideoxy-2-thio-D-galacto-2-nonulopyranosid)onate 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: 72.0%

Trimethyl(methylthio)silane (3908-55-2) + methyl 5-acetamido-2,8,9-tri-O-acetyl-4-O-benzoyl-3,5,7-trideoxy-D-galacto-2-nonulopyranosylonate (147906-98-7) → methyl (methyl 5-acetamido-8,9-di-O-acetyl-4-O-benzoyl-3,5,7-trideoxy-2-thio-D-galacto-2-nonulopyranosid)onate (147906-99-8)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; for 5.5h; Ambient temperature;

DOI:10.1016/0008-6215(92)84037-S

Reference yield:

benzoyl chloride (98-88-4) → methyl (methyl 5-acetamido-8,9-di-O-acetyl-4-O-benzoyl-3,5,7-trideoxy-2-thio-D-galacto-2-nonulopyranosid)onate (147906-99-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 6.1 g / pyridine / CH₂Cl₂ / 0.25 h / 0 °C

2: 48.5 percent / pyridine / 1 h / 60 °C

3: 92.5 percent / tributyltin hydride, α,α'-azobis-isobutyronitrile / toluene / 1 h / 100 °C

4: 84 percent / 80percent aq. acetic acid / Ambient temperature

5: 98 percent / pyridine / Ambient temperature

6: BF₃*OEt₂ / CH₂Cl₂ / 9 h / 0 °C

7: pyridine / Ambient temperature

8: 72 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 5.5 h / Ambient temperature

With pyridine; trimethylsilyl trifluoromethanesulfonate; azobisisobutyronitrile; boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; acetic acid; In dichloromethane; toluene;

DOI:10.1016/0008-6215(92)84037-S

Reference yield:

methyl <2-(trimethylsilyl)ethyl 5-acetamido-3,5-dideoxy-8,9-O-isopropylidene-D-glycero-α-D-galacto-2-nonulopyranosid>onate (122777-23-5) → methyl (methyl 5-acetamido-8,9-di-O-acetyl-4-O-benzoyl-3,5,7-trideoxy-2-thio-D-galacto-2-nonulopyranosid)onate (147906-99-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 6.1 g / pyridine / CH₂Cl₂ / 0.25 h / 0 °C

2: 48.5 percent / pyridine / 1 h / 60 °C

3: 92.5 percent / tributyltin hydride, α,α'-azobis-isobutyronitrile / toluene / 1 h / 100 °C

4: 84 percent / 80percent aq. acetic acid / Ambient temperature

5: 98 percent / pyridine / Ambient temperature

6: BF₃*OEt₂ / CH₂Cl₂ / 9 h / 0 °C

7: pyridine / Ambient temperature

8: 72 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 5.5 h / Ambient temperature

With pyridine; trimethylsilyl trifluoromethanesulfonate; azobisisobutyronitrile; boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; acetic acid; In dichloromethane; toluene;

DOI:10.1016/0008-6215(92)84037-S

upstream raw materials:

Trimethyl(methylthio)silane

methyl 5-acetamido-2,8,9-tri-O-acetyl-4-O-benzoyl-3,5,7-trideoxy-D-galacto-2-nonulopyranosylonate

benzoyl chloride

methyl <2-(trimethylsilyl)ethyl 5-acetamido-3,5-dideoxy-8,9-O-isopropylidene-D-glycero-α-D-galacto-2-nonulopyranosid>onate

Downstream raw materials:

2-(trimethylsilyl)ethyl O-(methyl 5-acetamido-8,9-di-O-acetyl-4-O-benzoyl-3,5,7-trideoxy-α-D-galacto-2-nonulopyranosylonate)-(2->3)-O-(6-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,6-di-O-benzoyl-β-D-glucopyranoside

O-(methyl 5-acetamido-8,9-di-O-acetyl-4-O-benzoyl-3,5,7-trideoxy-α-D-galacto-2-nonulopyranosylonate)-(2->3)-O-(2,4-di-O-acetyl-6-O-benzoyl-β-D-galactopyranosyl)-(1->4)-3-O-acetyl-2,6-di-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate

2-(trimethylsilyl)ethyl O-(methyl 5-acetamido-8,9-di-O-acetyl-4-O-benzoyl-3,5,7-trideoxy-α-D-galacto-2-nonulopyranosylonate)-(2->3)-O-(2,4-di-O-acetyl-6-O-benzoyl-β-D-galactopyranosyl)-(1->4)-3-O-acetyl-2,6-di-O-benzoyl-β-D-glucopyranoside

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