(3aR,4S,7R,7aS)-dibenzyl 2,2-dimethyl-3a,4,7,7a-tetrahydro-4,7-(epoxyimino)benzo[d][1,3]dioxole-7a,8-dicarboxylate

Base Information

• Chemical Name: (3aR,4S,7R,7aS)-dibenzyl 2,2-dimethyl-3a,4,7,7a-tetrahydro-4,7-(epoxyimino)benzo[d][1,3]dioxole-7a,8-dicarboxylate
• CAS No.: 1301703-32-1
• Molecular Formula: C₂₅H₂₅NO₇
• Molecular Weight: 451.476
• Mol file: 1301703-32-1.mol

Synonyms:(3aR,4S,7R,7aS)-dibenzyl 2,2-dimethyl-3a,4,7,7a-tetrahydro-4,7-(epoxyimino)benzo[d][1,3]dioxole-7a,8-dicarboxylate

Chemical Property of (3aR,4S,7R,7aS)-dibenzyl 2,2-dimethyl-3a,4,7,7a-tetrahydro-4,7-(epoxyimino)benzo[d][1,3]dioxole-7a,8-dicarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4S,7R,7aS)-dibenzyl 2,2-dimethyl-3a,4,7,7a-tetrahydro-4,7-(epoxyimino)benzo[d][1,3]dioxole-7a,8-dicarboxylate

There total 3 articles about (3aR,4S,7R,7aS)-dibenzyl 2,2-dimethyl-3a,4,7,7a-tetrahydro-4,7-(epoxyimino)benzo[d][1,3]dioxole-7a,8-dicarboxylate 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: 58.0%

Benzyl N-hydroxycarbamate (3426-71-9) + (3aS,7aR)-benzyl 2,2-dimethyl-3a,7a-dihydrobenzo[d][1,3]dioxole-3a-carboxylate (1301703-27-4) → (3aR,4R,7S,7aR)-dibenzyl 2,2-dimethyl-3a,4,7,7a-tetrahydro-4,7-(epoxyimino)-benzo[d][1,3]dioxole-3a,8-dicarboxylate (1301703-31-0) + (3aR,4S,7R,7aS)-dibenzyl 2,2-dimethyl-3a,4,7,7a-tetrahydro-4,7-(epoxyimino)benzo[d][1,3]dioxole-7a,8-dicarboxylate (1301703-32-1)

Guidance literature:

With tetrabutylammonium periodite; In dichloromethane; at -78 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1039/c1cc10643k

Reference yield:

(-)-(3aS,7aR)-2,2-dimethyl-3a,7a-dihydrobenzo[d][1,3]dioxole-3a-carboxylic acid (172877-74-6) → (3aR,4S,7R,7aS)-dibenzyl 2,2-dimethyl-3a,4,7,7a-tetrahydro-4,7-(epoxyimino)benzo[d][1,3]dioxole-7a,8-dicarboxylate (1301703-32-1)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere

2: tetrabutylammonium periodite / dichloromethane / 2 h / -78 - 20 °C / Inert atmosphere

With tetrabutylammonium periodite; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/c1cc10643k

Reference yield:

(1S,2R)-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylic acid (32359-20-9) → (3aR,4S,7R,7aS)-dibenzyl 2,2-dimethyl-3a,4,7,7a-tetrahydro-4,7-(epoxyimino)benzo[d][1,3]dioxole-7a,8-dicarboxylate (1301703-32-1)

Guidance literature:

Multi-step reaction with 3 steps

1: toluene-4-sulfonic acid / acetone

2: triethylamine / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere

3: tetrabutylammonium periodite / dichloromethane / 2 h / -78 - 20 °C / Inert atmosphere

With tetrabutylammonium periodite; toluene-4-sulfonic acid; triethylamine; In dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1039/c1cc10643k

upstream raw materials:

Benzyl N-hydroxycarbamate

(3aS,7aR)-benzyl 2,2-dimethyl-3a,7a-dihydrobenzo[d][1,3]dioxole-3a-carboxylate

(1S,2R)-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylic acid

(-)-(3aS,7aR)-2,2-dimethyl-3a,7a-dihydrobenzo[d][1,3]dioxole-3a-carboxylic acid

Downstream raw materials:

(3aR,4S,5S,6S,7R,7aS)-dibenzyl 5,6-dihydroxy-2,2-dimethylhexahydro-4,7-(epoxyimino)benzo[d][1,3]dioxole-7a,8-dicarboxylate

(1R,2S,3R,4S,5S,6S)-2-carboxy-2,3,4,5,6-pentahydroxycyclohexylammonium chloride