methyl 2,3,6-tri-O-benzyl-4-O-methyl-13C₆-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-13C₆-β-D-glucopyranoside

Base Information

• Chemical Name: methyl 2,3,6-tri-O-benzyl-4-O-methyl-13C₆-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-13C₆-β-D-glucopyranoside
• CAS No.: 869719-06-2
• Molecular Formula: C₅₆H₆₂O₁₁
• Molecular Weight: 922.97

Synonyms:methyl 2,3,6-tri-O-benzyl-4-O-methyl-13C₆-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-13C₆-β-D-glucopyranoside

Chemical Property of methyl 2,3,6-tri-O-benzyl-4-O-methyl-13C₆-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-13C₆-β-D-glucopyranoside

Chemical Property:

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Technology Process of methyl 2,3,6-tri-O-benzyl-4-O-methyl-13C₆-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-13C₆-β-D-glucopyranoside

There total 8 articles about methyl 2,3,6-tri-O-benzyl-4-O-methyl-13C₆-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-13C₆-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: 64.0%

methyl 2,3,6-tri-O-benzyl-13C6-β-D-glucopyranoside (869719-01-7) + 2,3,6-tri-O-benzyl-4-O-methyl-13C6-D-glucopyranosyl trichloroacetimidate (904299-04-3) → methyl 2,3,6-tri-O-benzyl-4-O-methyl-13C6-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-13C6-β-D-glucopyranoside (869719-06-2)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -72 ℃; for 1h;

DOI:10.1016/j.carres.2005.08.003

Reference yield:

methyl 13C6-β-D-glucopyranoside → methyl 2,3,6-tri-O-benzyl-4-O-methyl-13C6-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-13C6-β-D-glucopyranoside (869719-06-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 63 percent / p-TsOH*H₂O / dioxane / 3 h / 30 °C / 30 Torr

2: 44 percent / NaH dispersion in mineral oil; tetra-n-butylammonium iodide / tetrahydrofuran / Heating

3: 87 percent / triethylsilane; trifluoroacetic acid / CH₂Cl₂ / 6 h / 20 °C

4: 64 percent / BF₃*Et₂O / CH₂Cl₂ / 1 h / -72 °C

With triethylsilane; boron trifluoride diethyl etherate; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane;

DOI:10.1016/j.carres.2005.08.003

Reference yield:

methyl 4,6-O-benzylidene-13C6-β-D-glucopyranoside (869718-94-5) → methyl 2,3,6-tri-O-benzyl-4-O-methyl-13C6-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-13C6-β-D-glucopyranoside (869719-06-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 44 percent / NaH dispersion in mineral oil; tetra-n-butylammonium iodide / tetrahydrofuran / Heating

2: 87 percent / triethylsilane; trifluoroacetic acid / CH₂Cl₂ / 6 h / 20 °C

3: 64 percent / BF₃*Et₂O / CH₂Cl₂ / 1 h / -72 °C

With triethylsilane; boron trifluoride diethyl etherate; tetra-(n-butyl)ammonium iodide; sodium hydride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.carres.2005.08.003

upstream raw materials:

methyl 2,3,6-tri-O-benzyl-13C₆-β-D-glucopyranoside

2,3,6-tri-O-benzyl-4-O-methyl-13C₆-D-glucopyranosyl trichloroacetimidate

methyl 4,6-O-benzylidene-13C₆-β-D-glucopyranoside

methyl 2,3,6-tri-O-benzyl-4-O-methyl-13C₆-β-D-glucopyranoside

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