methyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(β-D-glucopyranosyl)-4-O-(α-L-rhamnopyranosyl)-β-D-glucopyranoside

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Chemical Name:methyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(β-D-glucopyranosyl)-4-O-(α-L-rhamnopyranosyl)-β-D-glucopyranoside
CAS No.:913174-10-4
Molecular Formula:C₂₈H₄₃NO₁₅
Molecular Weight:633.647
Hs Code.:

Synonyms:methyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(β-D-glucopyranosyl)-4-O-(α-L-rhamnopyranosyl)-β-D-glucopyranoside

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Chemical Property of methyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(β-D-glucopyranosyl)-4-O-(α-L-rhamnopyranosyl)-β-D-glucopyranoside

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Technology Process of methyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(β-D-glucopyranosyl)-4-O-(α-L-rhamnopyranosyl)-β-D-glucopyranoside

There total 6 articles about methyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(β-D-glucopyranosyl)-4-O-(α-L-rhamnopyranosyl)-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: 84.0%

: 913174-08-0
methyl 2-(N-acetylacetamido)-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-6-O-benzyl-2-deoxy-β-D-glucopyranoside

: 913174-10-4
methyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(β-D-glucopyranosyl)-4-O-(α-L-rhamnopyranosyl)-β-D-glucopyranoside

Guidance literature:: With sodium; In methanol; at 20 ℃; for 0.5h;
DOI:10.1016/j.carres.2006.07.006

Reference yield:

: 913174-04-6
methyl 2-acetamido-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

: 913174-10-4
methyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(β-D-glucopyranosyl)-4-O-(α-L-rhamnopyranosyl)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 89 percent / N,N-diisopropylethylamine; 4 A MS / CH₂Cl₂ / 20 °C

2: 62 percent / NaBH₃CN; HCl; 4 A MS / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C

3: 82 percent / 4 A MS; TESOTf / CH₂Cl₂ / 2 h / -78 - 20 °C

4: 84 percent / Na / methanol / 0.5 h / 20 °C

With hydrogenchloride; triethylsilyl trifluoromethyl sulfonate; sodium; sodium cyanoborohydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 4: Zemplen de-acetylation;
DOI:10.1016/j.carres.2006.07.006

Reference yield:

: 913174-06-8
methyl 2-(N-acetylacetamido)-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-6-O-benzyl-2-deoxy-β-D-glucopyranoside

: 913174-10-4
methyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(β-D-glucopyranosyl)-4-O-(α-L-rhamnopyranosyl)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 82 percent / 4 A MS; TESOTf / CH₂Cl₂ / 2 h / -78 - 20 °C

2: 84 percent / Na / methanol / 0.5 h / 20 °C

With triethylsilyl trifluoromethyl sulfonate; sodium; In methanol; dichloromethane; 2: Zemplen de-acetylation;
DOI:10.1016/j.carres.2006.07.006