methyl (1R,2R,3S,4S,5R,6R)-3-(benzyloxy)-2,4,5-trihydroxy-6-nitrocyclohexanecarboxylate

Base Information

Chemical Name:methyl (1R,2R,3S,4S,5R,6R)-3-(benzyloxy)-2,4,5-trihydroxy-6-nitrocyclohexanecarboxylate
CAS No.:1380312-78-6
Molecular Formula:C₁₅H₁₉NO₈
Molecular Weight:341.318
Hs Code.:

Synonyms:methyl (1R,2R,3S,4S,5R,6R)-3-(benzyloxy)-2,4,5-trihydroxy-6-nitrocyclohexanecarboxylate

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Chemical Property of methyl (1R,2R,3S,4S,5R,6R)-3-(benzyloxy)-2,4,5-trihydroxy-6-nitrocyclohexanecarboxylate

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Technology Process of methyl (1R,2R,3S,4S,5R,6R)-3-(benzyloxy)-2,4,5-trihydroxy-6-nitrocyclohexanecarboxylate

There total 4 articles about methyl (1R,2R,3S,4S,5R,6R)-3-(benzyloxy)-2,4,5-trihydroxy-6-nitrocyclohexanecarboxylate 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: 73.0%

: C₁₅H₁₉NO₈

: 77-76-9
2,2-dimethoxy-propane

: 1380312-78-6
methyl (1R,2R,3S,4S,5R,6R)-3-(benzyloxy)-2,4,5-trihydroxy-6-nitrocyclohexanecarboxylate

: 1380312-69-5
methyl (1R,2R,3S,4S,5S,6R)-3-(benzyloxy)-2-hydroxy-4,5-(isopropylidenedioxy)-6-nitrocyclohexanecarboxylate

Guidance literature:: With toluene-4-sulfonic acid; copper(II) sulfate; In acetone; at 20 ℃; for 24h; Inert atmosphere;
DOI:10.1002/ejoc.201200103

Reference yield:

: C₁₅H₁₉NO₈

: 1380312-68-4
methyl (1R,2R,3S,4S,5S,6R)-3-(benzyloxy)-2,4,5-trihydroxy-6-nitrocyclohexanecarboxylate

: 1380312-78-6
methyl (1R,2R,3S,4S,5R,6R)-3-(benzyloxy)-2,4,5-trihydroxy-6-nitrocyclohexanecarboxylate

Guidance literature:: With sodium hydrogencarbonate; In methanol; water; at 20 ℃; for 12h; optical yield given as %de; Inert atmosphere;
DOI:10.1002/ejoc.201200103

Reference yield:

: 1380312-65-1
3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-6-nitro-5-C-[tris(phenylthio)methyl]-α-D-glucofuranose

: 1380312-68-4
methyl (1R,2R,3S,4S,5S,6R)-3-(benzyloxy)-2,4,5-trihydroxy-6-nitrocyclohexanecarboxylate

: 1380312-78-6
methyl (1R,2R,3S,4S,5R,6R)-3-(benzyloxy)-2,4,5-trihydroxy-6-nitrocyclohexanecarboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: boron trifluoride diethyl etherate; water; mercury(II) oxide / tetrahydrofuran / 20 °C / Inert atmosphere

2: trifluoroacetic acid / water / 5 h / 20 °C / Inert atmosphere

3: sodium hydrogencarbonate / methanol; water / 12 h / 20 °C / Inert atmosphere

With boron trifluoride diethyl etherate; water; sodium hydrogencarbonate; trifluoroacetic acid; mercury(II) oxide; In tetrahydrofuran; methanol; water; 3: Henry reaction;
DOI:10.1002/ejoc.201200103