8-methoxycarbonyloctyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(4-methoxybenzyl)-4-O-(methylthio)thiocarbonyl-β-D-glucopyranoside

Base Information

• Chemical Name: 8-methoxycarbonyloctyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(4-methoxybenzyl)-4-O-(methylthio)thiocarbonyl-β-D-glucopyranoside
• CAS No.: 180335-96-0
• Molecular Formula: C₃₅H₄₉NO₉S₂
• Molecular Weight: 691.907

Synonyms:8-methoxycarbonyloctyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(4-methoxybenzyl)-4-O-(methylthio)thiocarbonyl-β-D-glucopyranoside

Chemical Property of 8-methoxycarbonyloctyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(4-methoxybenzyl)-4-O-(methylthio)thiocarbonyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 8-methoxycarbonyloctyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(4-methoxybenzyl)-4-O-(methylthio)thiocarbonyl-β-D-glucopyranoside

There total 4 articles about 8-methoxycarbonyloctyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(4-methoxybenzyl)-4-O-(methylthio)thiocarbonyl-β-D-glucopyranoside 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: 88.0%

carbon disulfide (75-15-0,12122-00-8) + 8-methoxycarbonyloctyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(4-methoxybenzyl)-β-D-glucopyranoside (152480-29-0) + methyl iodide (74-88-4) → 8-methoxycarbonyloctyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(4-methoxybenzyl)-4-O-(methylthio)thiocarbonyl-β-D-glucopyranoside (180335-96-0)

Guidance literature:

8-methoxycarbonyloctyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(4-methoxybenzyl)-β-D-glucopyranoside; With 1H-imidazole; sodium hydride; In tetrahydrofuran; for 0.5h; Heating;

carbon disulfide; In tetrahydrofuran; for 0.5h; Heating;

methyl iodide; In tetrahydrofuran; for 0.5h; Heating;

DOI:10.1016/0008-6215(96)00047-X

Reference yield:

ω-methoxycarbonyloctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (71048-95-8) → 8-methoxycarbonyloctyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(4-methoxybenzyl)-4-O-(methylthio)thiocarbonyl-β-D-glucopyranoside (180335-96-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / dimethylformamide / 0.5 h / -50 - -40 °C

1.2: 68 percent / dimethylformamide / 1 h / -50 - 20 °C

2.1: 83 percent / HCl; sodium cyanoborohydride; 3 Angstroem molecular sieves / diethyl ether; tetrahydrofuran / 0.67 h / 0 °C

3.1: imidazole; sodium hydride / tetrahydrofuran / 0.5 h / Heating

3.2: tetrahydrofuran / 0.5 h / Heating

3.3: 88 percent / tetrahydrofuran / 0.5 h / Heating

With 1H-imidazole; hydrogenchloride; 3 A molecular sieve; sodium hydride; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: benzylation / 2.1: Ring cleavage / 3.1: Metallation / 3.2: Addition / 3.3: Methylation;

DOI:10.1016/0008-6215(96)00047-X

Reference yield:

p-methoxybenzyl chloride (824-94-2) → 8-methoxycarbonyloctyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(4-methoxybenzyl)-4-O-(methylthio)thiocarbonyl-β-D-glucopyranoside (180335-96-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / dimethylformamide / 0.5 h / -50 - -40 °C

1.2: 68 percent / dimethylformamide / 1 h / -50 - 20 °C

2.1: 83 percent / HCl; sodium cyanoborohydride; 3 Angstroem molecular sieves / diethyl ether; tetrahydrofuran / 0.67 h / 0 °C

3.1: imidazole; sodium hydride / tetrahydrofuran / 0.5 h / Heating

3.2: tetrahydrofuran / 0.5 h / Heating

3.3: 88 percent / tetrahydrofuran / 0.5 h / Heating

With 1H-imidazole; hydrogenchloride; 3 A molecular sieve; sodium hydride; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: benzylation / 2.1: Ring cleavage / 3.1: Metallation / 3.2: Addition / 3.3: Methylation;

DOI:10.1016/0008-6215(96)00047-X

upstream raw materials:

carbon disulfide

8-methoxycarbonyloctyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(4-methoxybenzyl)-β-D-glucopyranoside

methyl iodide

ω-methoxycarbonyloctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

Downstream raw materials:

8-methoxycarbonyloctyl 2-acetamido-6-O-benzyl-2,4-dideoxy-3-O-(4-methoxybenzyl)-β-D-xylopyranoside

8-methoxycarbonyloctyl 2-acetamido-6-O-benzyl-2,4-dideoxy-β-D-xylopyranoside

8-methoxycarbonyloctyl 3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-6-O-benzyl-2,4-dideoxy-β-D-xylo-hexopyranoside

8-methoxycarbonyloctyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-6-O-benzyl-2,4-dideoxy-β-D-xylo-hexopyranoside

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