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

Base Information

Chemical Name:(1R,2S,4S,5S)-4-allyloxy-6-(2,4-dimethoxybenzyl)-2-<(1R)-1,2-O-isopropylideneethyl>-3-oxa-6-azabicyclo<3.2.0>heptan-7-one
CAS No.:151557-90-3
Molecular Formula:C₂₂H₂₉NO₇
Molecular Weight:419.475
Hs Code.:

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

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

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

There total 1 articles about (1R,2S,4S,5S)-4-allyloxy-6-(2,4-dimethoxybenzyl)-2-<(1R)-1,2-O-isopropylideneethyl>-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: 70.8%

: 556-56-9
allyl iodid

: 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

: 151557-90-3
(1R,2S,4S,5S)-4-allyloxy-6-(2,4-dimethoxybenzyl)-2-<(1R)-1,2-O-isopropylideneethyl>-3-oxa-6-azabicyclo<3.2.0>heptan-7-one

Guidance literature:: With silver(l) oxide; In N,N-dimethyl-formamide; Ambient temperature;
DOI:10.1246/bcsj.66.1709

Reference yield:

: 151557-90-3
(1R,2S,4S,5S)-4-allyloxy-6-(2,4-dimethoxybenzyl)-2-<(1R)-1,2-O-isopropylideneethyl>-3-oxa-6-azabicyclo<3.2.0>heptan-7-one

: 2-<(3R)-3-(benzyloxy)tetradecanoylamino>-3-C-<<(3R)-3-(benzyloxy)tetradecanoyloxy>methyl>-2,3-dideoxy-4,6-O-isopropylidene-D-mannopyranose

Guidance literature:: Multi-step reaction with 8 steps

1: LiAlH₄ / tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) RT, 30 min

2: 79.8 percent / dicyclohexylcarbodiimide (DCC), DMAP / CH₂Cl₂ / 10 h / Ambient temperature

3: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / CH₂Cl₂; H₂O / 2 h / Ambient temperature

4: Girard-T / ethanol / 3 h / Ambient temperature

5: DMAP, dicyclohexylcarbodiimide (DCC) / CH₂Cl₂ / 0.75 h / Ambient temperature

6: 1.) 8H₁₀)(PMePH₂)2>PF₆, H₂, 2.) H₂O, pyridine, I₂ / 1.) THF, RT, 2 h, 2.) THF, RT, 15 min

7: 90percent aq. AcOH / 4.5 h / 60 °C

8: TsOH-H₂O / dimethylformamide / Ambient temperature

With pyridine; dmap; lithium aluminium tetrahydride; PF6; water; hydrogen; iodine; Trimethylammoniumessigsaeurebetain-methylester-chlorid; toluene-4-sulfonic acid; acetic acid; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1246/bcsj.66.1709

Reference yield:

: 151557-90-3
(1R,2S,4S,5S)-4-allyloxy-6-(2,4-dimethoxybenzyl)-2-<(1R)-1,2-O-isopropylideneethyl>-3-oxa-6-azabicyclo<3.2.0>heptan-7-one

: 150799-06-7
allyl 2-<(3R)-3-(benzyloxy)tetradecanoylamino>-3-C-<<(3R)-3-(benzyloxy)tetradecanoyloxy>methyl>-2,3-dideoxy-4,6-O-isopropylidene-D-mannopyranoside

Guidance literature:: Multi-step reaction with 9 steps

1: LiAlH₄ / tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) RT, 30 min

2: 79.8 percent / dicyclohexylcarbodiimide (DCC), DMAP / CH₂Cl₂ / 10 h / Ambient temperature

3: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / CH₂Cl₂; H₂O / 2 h / Ambient temperature

4: Girard-T / ethanol / 3 h / Ambient temperature

5: DMAP, dicyclohexylcarbodiimide (DCC) / CH₂Cl₂ / 0.75 h / Ambient temperature

6: 1.) 8H₁₀)(PMePH₂)2>PF₆, H₂, 2.) H₂O, pyridine, I₂ / 1.) THF, RT, 2 h, 2.) THF, RT, 15 min

7: 90percent aq. AcOH / 4.5 h / 60 °C

8: TsOH-H₂O / dimethylformamide / Ambient temperature

9: 90 percent / Ag₂O / dimethylformamide / 5 h / Ambient temperature

With pyridine; dmap; lithium aluminium tetrahydride; PF6; water; hydrogen; iodine; Trimethylammoniumessigsaeurebetain-methylester-chlorid; toluene-4-sulfonic acid; acetic acid; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; silver(l) oxide; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1246/bcsj.66.1709