ethyl 6-deoxy-6-diazo-1,2-O-isopropylidene-3-O-(4'-methoxybenzyl)-α-D-xylo-hept-5-ulofuranuronate

Base Information

• Chemical Name: ethyl 6-deoxy-6-diazo-1,2-O-isopropylidene-3-O-(4'-methoxybenzyl)-α-D-xylo-hept-5-ulofuranuronate
• CAS No.: 262852-30-2
• Molecular Formula: C₂₀H₂₄N₂O₈
• Molecular Weight: 420.419

Synonyms:ethyl 6-deoxy-6-diazo-1,2-O-isopropylidene-3-O-(4'-methoxybenzyl)-α-D-xylo-hept-5-ulofuranuronate

Chemical Property of ethyl 6-deoxy-6-diazo-1,2-O-isopropylidene-3-O-(4'-methoxybenzyl)-α-D-xylo-hept-5-ulofuranuronate

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Technology Process of ethyl 6-deoxy-6-diazo-1,2-O-isopropylidene-3-O-(4'-methoxybenzyl)-α-D-xylo-hept-5-ulofuranuronate

There total 2 articles about ethyl 6-deoxy-6-diazo-1,2-O-isopropylidene-3-O-(4'-methoxybenzyl)-α-D-xylo-hept-5-ulofuranuronate 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: 86.0%

ethyl 6-deoxy-1,2-O-isopropylidene-3-O-(4'-methoxybenzyl)-α-D-xylo-hept-5-ulofuranuronate (262852-28-8) → ethyl 6-deoxy-6-diazo-1,2-O-isopropylidene-3-O-(4'-methoxybenzyl)-α-D-xylo-hept-5-ulofuranuronate (262852-30-2)

Guidance literature:

With triethylamine; Methanesulfonyl azide; In acetonitrile; at 20 ℃; for 3h;

DOI:10.1039/a908453c

Reference yield:

(3aR,5S,6S,6aR)-6-(4-methoxybenzyloxy)-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxole-5-carbaldehyde (82529-87-1) → ethyl 6-deoxy-6-diazo-1,2-O-isopropylidene-3-O-(4'-methoxybenzyl)-α-D-xylo-hept-5-ulofuranuronate (262852-30-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / BF₃*OEt₂ / CH₂Cl₂ / 3 h / -50 °C

2: 86 percent / NEt₃; methanesulfonyl azide / acetonitrile / 3 h / 20 °C

With boron trifluoride diethyl etherate; triethylamine; Methanesulfonyl azide; In dichloromethane; acetonitrile; 1: Decomposition / 2: Substitution;

DOI:10.1039/a908453c

Reference yield: 80.0%

ethyl 6-deoxy-6-diazo-1,2-O-isopropylidene-3-O-(4'-methoxybenzyl)-α-D-xylo-hept-5-ulofuranuronate (262852-30-2) → Ethyl 3,6-anhydro-1,2-O-isopropylidene-5-O-(4-methoxybenzyl)-α-D-xylo-hept-5-enofuranuronate

Guidance literature:

dirhodium tetraacetate; In benzene; for 0.416667h; Heating;

DOI:10.1039/a908453c

upstream raw materials:

ethyl 6-deoxy-1,2-O-isopropylidene-3-O-(4'-methoxybenzyl)-α-D-xylo-hept-5-ulofuranuronate

(3aR,5S,6S,6aR)-6-(4-methoxybenzyloxy)-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxole-5-carbaldehyde

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