methyl-3,5.6-tri-O-benzyl-2-O-(methoxycarbonylmethyl)-β-D-glucofuranoside

Base Information

• Chemical Name: methyl-3,5.6-tri-O-benzyl-2-O-(methoxycarbonylmethyl)-β-D-glucofuranoside
• CAS No.: 89733-69-7
• Molecular Formula: C₃₁H₃₆O₈
• Molecular Weight: 536.622

Synonyms:methyl-3,5.6-tri-O-benzyl-2-O-(methoxycarbonylmethyl)-β-D-glucofuranoside

Chemical Property of methyl-3,5.6-tri-O-benzyl-2-O-(methoxycarbonylmethyl)-β-D-glucofuranoside

Chemical Property:

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Technology Process of methyl-3,5.6-tri-O-benzyl-2-O-(methoxycarbonylmethyl)-β-D-glucofuranoside

There total 4 articles about methyl-3,5.6-tri-O-benzyl-2-O-(methoxycarbonylmethyl)-β-D-glucofuranoside 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: 75.0%

bromoacetic acid methyl ester (96-32-2) + methyl 3,5,6,-tri-O-benzyl-β-D-glucofuranoside (20822-89-3) → methyl-3,5.6-tri-O-benzyl-2-O-(methoxycarbonylmethyl)-β-D-glucofuranoside (89733-69-7)

Guidance literature:

With 1H-imidazole; tetrabutylammomium bromide; sodium hydride; In diethyl ether; for 4h;

DOI:10.1016/0008-6215(84)85162-9

Reference yield:

benzyl bromide (100-39-0) → methyl-3,5.6-tri-O-benzyl-2-O-(methoxycarbonylmethyl)-β-D-glucofuranoside (89733-69-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / NaH, tetrabutylammonium iodide / dimethylformamide / 24 h / 0 °C

2: H(+) ion exchange resin / 120 h / Heating

3: 75 percent / NaH, imidazole, tetrabutylammonium bromide / diethyl ether / 4 h

With 1H-imidazole; H(+) ion exchange resin; tetrabutylammomium bromide; tetra-(n-butyl)ammonium iodide; sodium hydride; In diethyl ether; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(84)85162-9

Reference yield:

1,2-O-isopropylidene-α-D-glucofuranose (18549-40-1) → methyl-3,5.6-tri-O-benzyl-2-O-(methoxycarbonylmethyl)-β-D-glucofuranoside (89733-69-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / NaH, tetrabutylammonium iodide / dimethylformamide / 24 h / 0 °C

2: H(+) ion exchange resin / 120 h / Heating

3: 75 percent / NaH, imidazole, tetrabutylammonium bromide / diethyl ether / 4 h

With 1H-imidazole; H(+) ion exchange resin; tetrabutylammomium bromide; tetra-(n-butyl)ammonium iodide; sodium hydride; In diethyl ether; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(84)85162-9

upstream raw materials:

bromoacetic acid methyl ester

methyl 3,5,6,-tri-O-benzyl-β-D-glucofuranoside

benzyl bromide

1,2-O-isopropylidene-3,5,6-tri-O-benzyl-α-D-glucofuranoside

Downstream raw materials:

methyl 3,5,6-tri-O-benzyl-2-O-(2-hydroxyethyl)-β-D-glucofuranoside

3,5,6-tri-O-benzyl-1-O-methyl-1,2-O-(1,2-ethanediyl)-4-O-(trichlorocarbamyl)-D-glucose

3,5.6-tri-O-benzyl-1,2-O-(1,2-ethanediyl)-α-D-glucofuranose

3,5,6-tri-O-benzyl-1-O-methyl-1,2-O-(1,2-ethanediyl)-D-glucose

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