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

Base Information

• Chemical Name: dimethyl (R^*)-2-<(R^*)-α-<(tert-butyldimethylsiloxy)methyl>-2,3,5-trimethoxy-4-methyl-6-phthalimidobenzyl>-1,1-cyclopropanedicarboxylate
• CAS No.: 79421-16-2
• Molecular Formula: C₃₃H₄₃NO₁₀Si
• Molecular Weight: 641.791

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

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

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

There total 14 articles about dimethyl (R^*)-2-<(R^*)-α-<(tert-butyldimethylsiloxy)methyl>-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%

tert-butyldimethylsilyl chloride (18162-48-6) + dimethyl (R*)-2-<(R*)-α-(hydroxymethyl)-2,3,5-trimethoxy-4-methyl-6-phthalimidobenzyl>-1,1-cyclopropanedicarboxylate (79421-15-1) → dimethyl (R*)-2-<(R*)-α-<(tert-butyldimethylsiloxy)methyl>-2,3,5-trimethoxy-4-methyl-6-phthalimidobenzyl>-1,1-cyclopropanedicarboxylate (79421-16-2)

Guidance literature:

With 4-pyrrolidin-1-ylpyridine; triethylamine; In dichloromethane; for 12h; Ambient temperature;

DOI:10.1021/jo00339a001

Reference yield:

phthalic anhydride (85-44-9) → dimethyl (R*)-2-<(R*)-α-<(tert-butyldimethylsiloxy)methyl>-2,3,5-trimethoxy-4-methyl-6-phthalimidobenzyl>-1,1-cyclopropanedicarboxylate (79421-16-2)

Guidance literature:

Multi-step reaction with 6 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

6: 87 percent / 4-pyrrolidinopyridine, Et₃N / CH₂Cl₂ / 12 h / Ambient temperature

With pyridine; 4-toluenesulfonyl azide; camphor-10-sulfonic acid; 4-pyrrolidin-1-ylpyridine; triethylamine; copper acetylacetonate; In diethyl ether; dichloromethane; chlorobenzene; toluene; acetonitrile;

DOI:10.1021/jo00339a001

Reference yield:

methyl <3-(2,3,5-trimethoxy-4-methyl-6-phthalimidophenyl)but-1-en-4-yl>malonate (65481-03-0) → dimethyl (R*)-2-<(R*)-α-<(tert-butyldimethylsiloxy)methyl>-2,3,5-trimethoxy-4-methyl-6-phthalimidobenzyl>-1,1-cyclopropanedicarboxylate (79421-16-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / tosyl azide, Et₃N / acetonitrile / 20 h / Ambient temperature

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

3: 87 percent / camphorsulfonic acid / 4 h / Heating

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

With 4-toluenesulfonyl azide; camphor-10-sulfonic acid; 4-pyrrolidin-1-ylpyridine; triethylamine; copper acetylacetonate; In dichloromethane; chlorobenzene; acetonitrile;

DOI:10.1021/jo00339a001

upstream raw materials:

tert-butyldimethylsilyl chloride

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

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

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