(3aR,5S,6R,7S,7aS)-5-azido-7-hydroxy-3-(4-methoxybenzyl)-6-(methoxymethoxy)hexahydrobenzo[d]oxazol-2(3H)-one

Base Information

Chemical Name:(3aR,5S,6R,7S,7aS)-5-azido-7-hydroxy-3-(4-methoxybenzyl)-6-(methoxymethoxy)hexahydrobenzo[d]oxazol-2(3H)-one
CAS No.:1554421-31-6
Molecular Formula:C₁₇H₂₂N₄O₆
Molecular Weight:378.385
Hs Code.:

Synonyms:(3aR,5S,6R,7S,7aS)-5-azido-7-hydroxy-3-(4-methoxybenzyl)-6-(methoxymethoxy)hexahydrobenzo[d]oxazol-2(3H)-one

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Chemical Property of (3aR,5S,6R,7S,7aS)-5-azido-7-hydroxy-3-(4-methoxybenzyl)-6-(methoxymethoxy)hexahydrobenzo[d]oxazol-2(3H)-one

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Technology Process of (3aR,5S,6R,7S,7aS)-5-azido-7-hydroxy-3-(4-methoxybenzyl)-6-(methoxymethoxy)hexahydrobenzo[d]oxazol-2(3H)-one

There total 6 articles about (3aR,5S,6R,7S,7aS)-5-azido-7-hydroxy-3-(4-methoxybenzyl)-6-(methoxymethoxy)hexahydrobenzo[d]oxazol-2(3H)-one 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: 100.0%

: 1554421-25-8
benzyl ((1R,2S,3R,4R,5S)-5-azido-2,3-dihydroxy-4-(methoxymethoxy)cyclohexyl)(4-methoxybenzyl)carbamate

: 1554421-31-6
(3aR,5S,6R,7S,7aS)-5-azido-7-hydroxy-3-(4-methoxybenzyl)-6-(methoxymethoxy)hexahydrobenzo[d]oxazol-2(3H)-one

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h; Inert atmosphere;
DOI:10.1016/j.bmcl.2013.12.125

Reference yield:

: 82509-76-0
dibenzyl (3aS,4R,5S,7R,7aS)-4-hydroxyhexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-5,7-diyldicarbamate

: 1554421-31-6
(3aR,5S,6R,7S,7aS)-5-azido-7-hydroxy-3-(4-methoxybenzyl)-6-(methoxymethoxy)hexahydrobenzo[d]oxazol-2(3H)-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: lithium hydroxide / 1,4-dioxane; water / 4 h / 70 °C

2.1: copper(ll) sulfate pentahydrate; triflic azide; potassium carbonate / methanol; dichloromethane; water / 18 h / 23 °C

3.1: tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

3.2: 16 h / 27 °C / Inert atmosphere

4.1: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide / 11 h / 0 - 23 °C / Inert atmosphere

5.1: acetic acid / water / 3 h / 23 °C

6.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

With copper(ll) sulfate pentahydrate; triflic azide; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; lithium hydroxide; In 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/j.bmcl.2013.12.125

Reference yield:

: 1554421-22-5
benzyl ((3aS,4R,5S,7R,7aS)-5-azido-4-hydroxyhexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexan]-7-yl)carbamate

: 1554421-31-6
(3aR,5S,6R,7S,7aS)-5-azido-7-hydroxy-3-(4-methoxybenzyl)-6-(methoxymethoxy)hexahydrobenzo[d]oxazol-2(3H)-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

1.2: 16 h / 27 °C / Inert atmosphere

2.1: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide / 11 h / 0 - 23 °C / Inert atmosphere

3.1: acetic acid / water / 3 h / 23 °C

4.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

With tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; In dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/j.bmcl.2013.12.125