Acetic acid (E)-3-[(4S,5S)-4-(benzyloxycarbonyl-methyl-amino)-1,3,4,5-tetrahydro-benzo[cd]indol-5-yl]-2-methyl-allyl ester

Base Information

• Chemical Name: Acetic acid (E)-3-[(4S,5S)-4-(benzyloxycarbonyl-methyl-amino)-1,3,4,5-tetrahydro-benzo[cd]indol-5-yl]-2-methyl-allyl ester
• CAS No.: 77784-57-7
• Molecular Formula: C₂₆H₂₈N₂O₄
• Molecular Weight: 432.519
• Mol file: 77784-57-7.mol

Synonyms:

Chemical Property of Acetic acid (E)-3-[(4S,5S)-4-(benzyloxycarbonyl-methyl-amino)-1,3,4,5-tetrahydro-benzo[cd]indol-5-yl]-2-methyl-allyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (E)-3-[(4S,5S)-4-(benzyloxycarbonyl-methyl-amino)-1,3,4,5-tetrahydro-benzo[cd]indol-5-yl]-2-methyl-allyl ester

There total 4 articles about Acetic acid (E)-3-[(4S,5S)-4-(benzyloxycarbonyl-methyl-amino)-1,3,4,5-tetrahydro-benzo[cd]indol-5-yl]-2-methyl-allyl 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: 22.0%

Acetic acid 3-[(4S,5S)-4-(benzyloxycarbonyl-methyl-amino)-1,3,4,5-tetrahydro-benzo[cd]indol-5-yl]-2-hydroxy-2-methyl-propyl ester (77784-55-5) → Acetic acid (E)-3-[(4S,5S)-4-(benzyloxycarbonyl-methyl-amino)-1,3,4,5-tetrahydro-benzo[cd]indol-5-yl]-2-methyl-allyl ester (77784-57-7) + Acetic acid 2-[(4S,5S)-4-(benzyloxycarbonyl-methyl-amino)-1,3,4,5-tetrahydro-benzo[cd]indol-5-ylmethyl]-allyl ester (77784-56-6)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; Heating;

Reference yield:

Methyl-[(4S,5S)-5-(2-methyl-allyl)-1,3,4,5-tetrahydro-benzo[cd]indol-4-yl]-carbamic acid benzyl ester (77784-53-3) → Acetic acid (E)-3-[(4S,5S)-4-(benzyloxycarbonyl-methyl-amino)-1,3,4,5-tetrahydro-benzo[cd]indol-5-yl]-2-methyl-allyl ester (77784-57-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / OsO₄ / diethyl ether; pyridine / 0 - 20 °C

2: 100 percent / pyridine

3: 25 percent / p-TsOH / benzene / Heating

With osmium(VIII) oxide; toluene-4-sulfonic acid; In pyridine; diethyl ether; benzene;

Reference yield:

[(4S,5S)-5-(2,3-Dihydroxy-2-methyl-propyl)-1,3,4,5-tetrahydro-benzo[cd]indol-4-yl]-methyl-carbamic acid benzyl ester (77784-54-4) → Acetic acid (E)-3-[(4S,5S)-4-(benzyloxycarbonyl-methyl-amino)-1,3,4,5-tetrahydro-benzo[cd]indol-5-yl]-2-methyl-allyl ester (77784-57-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / pyridine

2: 25 percent / p-TsOH / benzene / Heating

With toluene-4-sulfonic acid; In pyridine; benzene;

upstream raw materials:

acetic anhydride

(+/-)-chanoclavine I

benzyl chloroformate

Acetic acid 3-[(4S,5S)-4-(benzyloxycarbonyl-methyl-amino)-1,3,4,5-tetrahydro-benzo[cd]indol-5-yl]-2-hydroxy-2-methyl-propyl ester

Downstream raw materials:

(+/-)-chanoclavine I

Acetic acid 2-[(4S,5S)-4-(benzyloxycarbonyl-methyl-amino)-1,3,4,5-tetrahydro-benzo[cd]indol-5-ylmethyl]-allyl ester