1,3,4,6-tetra-O-acetyl-2-deoxy-2-N-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl]amino-D-glucopyranose

Base Information

• Chemical Name: 1,3,4,6-tetra-O-acetyl-2-deoxy-2-N-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl]amino-D-glucopyranose
• CAS No.: 412036-89-6
• Molecular Formula: C₂₄H₃₃NO₁₁
• Molecular Weight: 511.526

Synonyms:1,3,4,6-tetra-O-acetyl-2-deoxy-2-N-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl]amino-D-glucopyranose

Chemical Property of 1,3,4,6-tetra-O-acetyl-2-deoxy-2-N-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl]amino-D-glucopyranose

Chemical Property:

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Technology Process of 1,3,4,6-tetra-O-acetyl-2-deoxy-2-N-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl]amino-D-glucopyranose

There total 2 articles about 1,3,4,6-tetra-O-acetyl-2-deoxy-2-N-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl]amino-D-glucopyranose 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:

2-acetyldimedone (1755-15-3) → 1,3,4,6-tetra-O-acetyl-2-deoxy-2-N-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl]amino-D-glucopyranose (412036-89-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / sodium methoxide / methanol / 5 h / Heating

2: 86 percent / pyridine / 20 °C

With pyridine; sodium methylate; In methanol;

DOI:10.1080/07328300500388685

Reference yield:

(+)-D-glucosamine hydrochloride (1078691-95-8) → 1,3,4,6-tetra-O-acetyl-2-deoxy-2-N-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl]amino-D-glucopyranose (412036-89-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / sodium methoxide / methanol / 5 h / Heating

2: 86 percent / pyridine / 20 °C

With pyridine; sodium methylate; In methanol;

DOI:10.1080/07328300500388685

Reference yield: 91.0%

1,3,4,6-tetra-O-acetyl-2-deoxy-2-N-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl]amino-D-glucopyranose (412036-89-6) → 3,4,6-tri-O-acetyl-2-deoxy-2-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-ethylamino]-α-D-glucopyranosyl bromide (212394-16-6)

Guidance literature:

With hydrogen bromide; acetic acid; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1080/07328300500388685

upstream raw materials:

2-acetyldimedone

(+)-D-glucosamine hydrochloride

Downstream raw materials:

3,4,6-tri-O-acetyl-2-deoxy-2-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-ethylamino]-α-D-glucopyranosyl bromide

methyl 4,6-O-benzylidene-2-deoxy-2-N-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl]amino-1-thio-β-D-glucopyranoside

methyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl]amino-1-thio-β-D-glucopyranoside

2-Deoxy-2-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethylamino]-1-thio-3,4,6-tri-O-acetyl-β-D-glucopyranose

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