methyl 2,3,6-tri-O-benzyl-4-O-(4,6-O-benzylidene-2,3-di-O-methyl-α-L-idopyranosyl)-α-D-glucopyranoside

Base Information

Chemical Name:methyl 2,3,6-tri-O-benzyl-4-O-(4,6-O-benzylidene-2,3-di-O-methyl-α-L-idopyranosyl)-α-D-glucopyranoside
CAS No.:1186009-53-9
Molecular Formula:C₄₃H₅₀O₁₁
Molecular Weight:742.863
Hs Code.:

Synonyms:methyl 2,3,6-tri-O-benzyl-4-O-(4,6-O-benzylidene-2,3-di-O-methyl-α-L-idopyranosyl)-α-D-glucopyranoside

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Chemical Property of methyl 2,3,6-tri-O-benzyl-4-O-(4,6-O-benzylidene-2,3-di-O-methyl-α-L-idopyranosyl)-α-D-glucopyranoside

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Technology Process of methyl 2,3,6-tri-O-benzyl-4-O-(4,6-O-benzylidene-2,3-di-O-methyl-α-L-idopyranosyl)-α-D-glucopyranoside

There total 9 articles about methyl 2,3,6-tri-O-benzyl-4-O-(4,6-O-benzylidene-2,3-di-O-methyl-α-L-idopyranosyl)-α-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: 97.0%

: 1186009-51-7
C₄₂H₄₈O₁₁

: 77-78-1
dimethyl sulfate

: 1186009-53-9
methyl 2,3,6-tri-O-benzyl-4-O-(4,6-O-benzylidene-2,3-di-O-methyl-α-L-idopyranosyl)-α-D-glucopyranoside

Guidance literature:: With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃;
DOI:10.1016/j.bmcl.2009.03.155

Reference yield: 90.0%

: 1186009-49-3
methyl 2,3,6-tri-O-benzyl-4-O-(2-O-benzoyl-4,6-O-benzylidene-3-O-methyl-α-L-idopyranosyl)-α-D-glucopyranoside

: 74-88-4
methyl iodide

: 1186009-53-9
methyl 2,3,6-tri-O-benzyl-4-O-(4,6-O-benzylidene-2,3-di-O-methyl-α-L-idopyranosyl)-α-D-glucopyranoside

Guidance literature:: methyl 2,3,6-tri-O-benzyl-4-O-(2-O-benzoyl-4,6-O-benzylidene-3-O-methyl-α-L-idopyranosyl)-α-D-glucopyranoside; With sodium methylate; In methanol; water; at 20 ℃; for 1h;

With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 0.25h; Inert atmosphere;

methyl iodide; In N-Methylformamide; N,N-dimethyl-formamide; at 0 ℃; for 3h; Inert atmosphere;
DOI:10.1021/jacs.9b03266

Reference yield:

: 4-methylphenyl 4-O-(4,6-O-benzylidine-2,3-di-O-methyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside

: 1186009-53-9
methyl 2,3,6-tri-O-benzyl-4-O-(4,6-O-benzylidene-2,3-di-O-methyl-α-L-idopyranosyl)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1.1: 1H-imidazole / dichloromethane / 3 h / 20 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 0 °C

3.1: acetic acid / water / 3 h / 70 °C

4.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 2 h / 0 - 20 °C

5.1: (R)-10-camphorsulfonic acid / acetonitrile / 12 h / 20 °C

6.1: pyridine / 12 h / 0 - 20 °C

7.1: trimethylsilyl trifluoromethanesulfonate; N-iodo-succinimide / dichloromethane / 0.58 h / -20 - 0 °C / Molecular sieve; Inert atmosphere

8.1: sodium methylate / water; methanol / 1 h / 20 °C

8.2: 0.25 h / 0 °C / Inert atmosphere

8.3: 3 h / 0 °C / Inert atmosphere

With pyridine; 1H-imidazole; N-iodo-succinimide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trimethylsilyl trifluoromethanesulfonate; [bis(acetoxy)iodo]benzene; (R)-10-camphorsulfonic acid; sodium methylate; sodium hydride; acetic acid; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; mineral oil;
DOI:10.1021/jacs.9b03266