ethyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

Base Information

• Chemical Name: ethyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside
• CAS No.: 192936-00-8
• Molecular Formula: C₂₄H₂₈O₆S
• Molecular Weight: 444.549

Synonyms:ethyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

Chemical Property of ethyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

Chemical Property:

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Technology Process of ethyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

There total 3 articles about ethyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 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: 98.5%

acetic anhydride (108-24-7) + ethyl 3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside (173935-67-6) → ethyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside (192936-00-8)

Guidance literature:

In pyridine; at 20 ℃; for 3h;

DOI:10.1016/S0008-6215(00)00011-2

Reference yield:

benzyl bromide (100-39-0) → ethyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside (192936-00-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Bu₂SnO / benzene / 6 h / Heating

1.2: 81 percent / Bu₄NBr / benzene / 65 °C

2.1: 98.5 percent / pyridine / 3 h / 20 °C

With di(n-butyl)tin oxide; In pyridine; benzene; 1.1: stannylation / 1.2: benzylation / 2.1: Acetylation;

DOI:10.1016/S0008-6215(00)00011-2

Reference yield:

S-ethyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside (142924-31-0) → ethyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside (192936-00-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Bu₂SnO / benzene / 6 h / Heating

1.2: 81 percent / Bu₄NBr / benzene / 65 °C

2.1: 98.5 percent / pyridine / 3 h / 20 °C

With di(n-butyl)tin oxide; In pyridine; benzene; 1.1: stannylation / 1.2: benzylation / 2.1: Acetylation;

DOI:10.1016/S0008-6215(00)00011-2

upstream raw materials:

acetic anhydride

ethyl 3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

benzyl bromide

S-ethyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside

Downstream raw materials:

2-(trimethylsilyl)ethyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->3)-4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

2-(4-methoxyphenoxy)ethyl (2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl)-(1->3)-2-azido-4,6-Obenzylidene-2-deoxy-β-D-galactopyranoside

2-trimethylsilylethyl (2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl)-(1→2)-3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranoside

2-(trimethylsilyl)ethyl 2-O-acetyl-3,6-di-O-benzyl-α-D-mannopyranosyl-(1->3)-4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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