(1R,2S,4S,5S)-6-(2,4-dimethoxybenzyl)-4-hydroxy-2-<(1R)-1,2-isopropyridenedioxyethyl>-3-oxa-6-azabicyclo<3.2.0>heptan-7-one

Base Information

Chemical Name:(1R,2S,4S,5S)-6-(2,4-dimethoxybenzyl)-4-hydroxy-2-<(1R)-1,2-isopropyridenedioxyethyl>-3-oxa-6-azabicyclo<3.2.0>heptan-7-one
CAS No.:114827-87-1
Molecular Formula:C₁₉H₂₅NO₇
Molecular Weight:379.41
Hs Code.:

Synonyms:(1R,2S,4S,5S)-6-(2,4-dimethoxybenzyl)-4-hydroxy-2-<(1R)-1,2-isopropyridenedioxyethyl>-3-oxa-6-azabicyclo<3.2.0>heptan-7-one

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Chemical Property of (1R,2S,4S,5S)-6-(2,4-dimethoxybenzyl)-4-hydroxy-2-<(1R)-1,2-isopropyridenedioxyethyl>-3-oxa-6-azabicyclo<3.2.0>heptan-7-one

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Technology Process of (1R,2S,4S,5S)-6-(2,4-dimethoxybenzyl)-4-hydroxy-2-<(1R)-1,2-isopropyridenedioxyethyl>-3-oxa-6-azabicyclo<3.2.0>heptan-7-one

There total 12 articles about (1R,2S,4S,5S)-6-(2,4-dimethoxybenzyl)-4-hydroxy-2-<(1R)-1,2-isopropyridenedioxyethyl>-3-oxa-6-azabicyclo<3.2.0>heptan-7-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: 79.0%

: 114827-85-9,114884-32-1,118100-18-8
(1R,2S,4RS,5R)-6-(2,4-dimethoxybenzyl)-4-hydroxy-2-<(1R)-1,2-isopropylidenedioxyethyl>-3-oxa-7-oxo-6-azabicyclo<3.2.0>heptane-5-carboxylate

: 114827-87-1
(1R,2S,4S,5S)-6-(2,4-dimethoxybenzyl)-4-hydroxy-2-<(1R)-1,2-isopropyridenedioxyethyl>-3-oxa-6-azabicyclo<3.2.0>heptan-7-one

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In pyridine; water; for 0.75h; Heating;
DOI:10.1246/cl.1987.1403

Reference yield:

: 15186-48-8
2,3-isopropylidene-glyceraldehyde

: 114827-87-1
(1R,2S,4S,5S)-6-(2,4-dimethoxybenzyl)-4-hydroxy-2-<(1R)-1,2-isopropyridenedioxyethyl>-3-oxa-6-azabicyclo<3.2.0>heptan-7-one

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) 55percent NaH (in mineral oil), 2.) acetic acid / 1.) DMSO, 1.5 h, room temperature, 2.) DMSO, 20 h, room temperature

2: 45 percent / DCC / CH₂Cl₂ / 0.5 h / Ambient temperature

3: 52 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / benzene / Heating

4: 98 percent / silicagel powder, NaBH₄ / methanol / 0.25 h

5: 79 percent / H₂O, 1,8-diazabicyclo<5.4.0>undec-7-ene / pyridine / 0.75 h / Heating

With sodium tetrahydroborate; water; silica gel; sodium hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; In pyridine; methanol; dichloromethane; benzene;
DOI:10.1246/bcsj.62.3950

Reference yield:

: 114827-84-8
ethyl (1R,2S,5R)-6-(2,4-dimethoxybenzyl)-4,7-dioxo-2-<(1R)-1,2-isopropylidenedioxyethyl>-3-oxa-6-azabicyclo-<3.2.0>heptane-5-carboxylate

: 114827-87-1
(1R,2S,4S,5S)-6-(2,4-dimethoxybenzyl)-4-hydroxy-2-<(1R)-1,2-isopropyridenedioxyethyl>-3-oxa-6-azabicyclo<3.2.0>heptan-7-one

Guidance literature:: Multi-step reaction with 2 steps

1: 98 percent / silicagel powder, NaBH₄ / methanol / 0.25 h

2: 79 percent / H₂O, 1,8-diazabicyclo<5.4.0>undec-7-ene / pyridine / 0.75 h / Heating

With sodium tetrahydroborate; water; silica gel; 1,8-diazabicyclo[5.4.0]undec-7-ene; In pyridine; methanol;
DOI:10.1246/bcsj.62.3950