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

Base Information

• Chemical Name: dimethyl (R^*)-2-<(R^*)-α-(hydroxymethyl)-2,3,5-trimethoxy-4-methyl-6-phthalimidobenzyl>-1,1-cyclopropanedicarboxylate
• CAS No.: 79421-15-1
• Molecular Formula: C₂₇H₂₉NO₁₀
• Molecular Weight: 527.528

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

Chemical Property of dimethyl (R^*)-2-<(R^*)-α-(hydroxymethyl)-2,3,5-trimethoxy-4-methyl-6-phthalimidobenzyl>-1,1-cyclopropanedicarboxylate

Chemical Property:

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Technology Process of dimethyl (R^*)-2-<(R^*)-α-(hydroxymethyl)-2,3,5-trimethoxy-4-methyl-6-phthalimidobenzyl>-1,1-cyclopropanedicarboxylate

There total 13 articles about dimethyl (R^*)-2-<(R^*)-α-(hydroxymethyl)-2,3,5-trimethoxy-4-methyl-6-phthalimidobenzyl>-1,1-cyclopropanedicarboxylate 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: 87.0%

methanol (67-56-1) + (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 (79465-33-1) → dimethyl (R*)-2-<(R*)-α-(hydroxymethyl)-2,3,5-trimethoxy-4-methyl-6-phthalimidobenzyl>-1,1-cyclopropanedicarboxylate (79421-15-1)

Guidance literature:

With camphor-10-sulfonic acid; for 4h; Heating;

DOI:10.1021/jo00339a001

Reference yield:

phthalic anhydride (85-44-9) → dimethyl (R*)-2-<(R*)-α-(hydroxymethyl)-2,3,5-trimethoxy-4-methyl-6-phthalimidobenzyl>-1,1-cyclopropanedicarboxylate (79421-15-1)

Guidance literature:

Multi-step reaction with 5 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

5: 87 percent / camphorsulfonic acid / 4 h / Heating

With pyridine; 4-toluenesulfonyl azide; camphor-10-sulfonic acid; triethylamine; copper acetylacetonate; In diethyl ether; chlorobenzene; toluene; acetonitrile;

DOI:10.1021/jo00339a001

Reference yield:

3-(2,3,5-trimethoxy-4-methyl-6-phthalimidophenyl)but-1-en-4-ol (65481-02-9) → dimethyl (R*)-2-<(R*)-α-(hydroxymethyl)-2,3,5-trimethoxy-4-methyl-6-phthalimidobenzyl>-1,1-cyclopropanedicarboxylate (79421-15-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / pyridine / diethyl ether / 5 h / 0 °C

2: 80 percent / tosyl azide, Et₃N / acetonitrile / 20 h / Ambient temperature

3: 35 percent / Cu(acac)2 / chlorobenzene / 1 h / 125 °C

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

With pyridine; 4-toluenesulfonyl azide; camphor-10-sulfonic acid; triethylamine; copper acetylacetonate; In diethyl ether; chlorobenzene; acetonitrile;

DOI:10.1021/jo00339a001

upstream raw materials:

methanol

(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

phthalic anhydride

3-(2,3,5-trimethoxy-4-methyl-6-phthalimidophenyl)but-1-en-4-ol

Downstream raw materials:

(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

dimethyl (R^*)-2-<(R^*)-α-<(tert-butyldimethylsiloxy)methyl>-2,3,5-trimethoxy-4-methyl-6-phthalimidobenzyl>-1,1-cyclopropanedicarboxylate

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