(1R,5S,6R)-5-[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3,5,6-trimethoxy-4-methyl-phenyl]-2-oxo-3-oxa-bicyclo[4.1.0]heptane-1-carboxylic acid methyl ester

Base Information

Chemical Name:(1R,5S,6R)-5-[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3,5,6-trimethoxy-4-methyl-phenyl]-2-oxo-3-oxa-bicyclo[4.1.0]heptane-1-carboxylic acid methyl ester
CAS No.:79465-33-1
Molecular Formula:C₂₆H₂₅NO₉
Molecular Weight:495.486
Hs Code.:

Synonyms:(1R,5S,6R)-5-[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3,5,6-trimethoxy-4-methyl-phenyl]-2-oxo-3-oxa-bicyclo[4.1.0]heptane-1-carboxylic acid methyl ester

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Chemical Property of (1R,5S,6R)-5-[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3,5,6-trimethoxy-4-methyl-phenyl]-2-oxo-3-oxa-bicyclo[4.1.0]heptane-1-carboxylic acid methyl ester

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Technology Process of (1R,5S,6R)-5-[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3,5,6-trimethoxy-4-methyl-phenyl]-2-oxo-3-oxa-bicyclo[4.1.0]heptane-1-carboxylic acid methyl ester

There total 1 articles about (1R,5S,6R)-5-[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3,5,6-trimethoxy-4-methyl-phenyl]-2-oxo-3-oxa-bicyclo[4.1.0]heptane-1-carboxylic acid methyl ester 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:

: 85-44-9
phthalic anhydride

: 79465-33-1
(1R,5S,6R)-5-[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3,5,6-trimethoxy-4-methyl-phenyl]-2-oxo-3-oxa-bicyclo[4.1.0]heptane-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: Et₃N / toluene / 2 h / Heating

2: 86 percent / pyridine / diethyl ether / 5 h / 0 °C

3: 80 percent / tosyl azide, Et₃N / acetonitrile / 20 h / Ambient temperature

4: 35 percent / Cu(acac)2 / chlorobenzene / 1 h / 125 °C

With pyridine; 4-toluenesulfonyl azide; triethylamine; copper acetylacetonate; In diethyl ether; chlorobenzene; toluene; acetonitrile;
DOI:10.1021/jo00339a001

Reference yield: 87.0%

: 67-56-1
methanol

: 79465-33-1
(1R,5S,6R)-5-[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3,5,6-trimethoxy-4-methyl-phenyl]-2-oxo-3-oxa-bicyclo[4.1.0]heptane-1-carboxylic acid methyl ester

: 79421-15-1
dimethyl (R^*)-2-<(R^*)-α-(hydroxymethyl)-2,3,5-trimethoxy-4-methyl-6-phthalimidobenzyl>-1,1-cyclopropanedicarboxylate

Guidance literature:: With camphor-10-sulfonic acid; for 4h; Heating;
DOI:10.1021/jo00339a001

Reference yield:

: 79465-33-1
(1R,5S,6R)-5-[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3,5,6-trimethoxy-4-methyl-phenyl]-2-oxo-3-oxa-bicyclo[4.1.0]heptane-1-carboxylic acid methyl ester

: 79421-20-8
(9R^*,9aS^*)-9-<(tert-butyldimethylsiloxy)methyl>-2,3,9,9a-tetrahydro-5,7,8-trimethoxy-6-methyl-2-(phenylselenyl)-1H-pyrrolo<1,2-a>indole

Guidance literature:: Multi-step reaction with 8 steps

1: 87 percent / camphorsulfonic acid / 4 h / Heating

2: 87 percent / 4-pyrrolidinopyridine, Et₃N / CH₂Cl₂ / 12 h / Ambient temperature

3: MeNHNH₂ / CHCl₃ / 60 h / Heating

4: methanol / 20 h / Heating

5: 58 percent / camphorsulfonic acid / toluene / 1 h / Heating

6: 1) NaH / 1) THF, pentane, 20 min, 2) THF, 10 min

7: 72 percent / 10percent aq. KOH / tetrahydrofuran / 3 h / Ambient temperature

8: 83 percent / BH₃ / tetrahydrofuran / 1 h / Heating

With potassium hydroxide; camphor-10-sulfonic acid; borane; sodium hydride; 4-pyrrolidin-1-ylpyridine; triethylamine; methylhydrazine; In tetrahydrofuran; methanol; dichloromethane; chloroform; toluene;
DOI:10.1021/jo00339a001