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

Base Information

• Chemical Name: (3aS,7aR)-benzyl 2,2-dimethyl-3a,7a-dihydrobenzo[d][1,3]dioxole-3a-carboxylate
• CAS No.: 1301703-27-4
• Molecular Formula: C₁₇H₁₈O₄
• Molecular Weight: 286.328
• Mol file: 1301703-27-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (3aS,7aR)-benzyl 2,2-dimethyl-3a,7a-dihydrobenzo[d][1,3]dioxole-3a-carboxylate 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:

benzyl bromide (100-39-0) + (-)-(3aS,7aR)-2,2-dimethyl-3a,7a-dihydrobenzo[d][1,3]dioxole-3a-carboxylic acid (172877-74-6) → (3aS,7aR)-benzyl 2,2-dimethyl-3a,7a-dihydrobenzo[d][1,3]dioxole-3a-carboxylate (1301703-27-4)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1039/c1cc10643k

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)-benzyl 2,2-dimethyl-3a,7a-dihydrobenzo[d][1,3]dioxole-3a-carboxylate (1301703-27-4) → (3aS,4R,7S,7aR)-benzyl 4-(benzyloxycarbonylamino)-7-hydroxy-2,2-dimethyl-3a,4,7,7a-tetrahydrobenzo[d][1,3]dioxole-3a-carboxylate (1301703-33-2)

Guidance literature:

Multi-step reaction with 2 steps

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

2: molybdenum hexacarbonyl / water; acetonitrile / 72 h / Reflux; Inert atmosphere

With tetrabutylammonium periodite; molybdenum hexacarbonyl; In dichloromethane; water; acetonitrile;

DOI:10.1039/c1cc10643k

upstream raw materials:

benzyl bromide

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

Downstream raw materials:

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

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

(3aS,4R,7S,7aR)-benzyl 4-(benzyloxycarbonylamino)-7-hydroxy-2,2-dimethyl-3a,4,7,7a-tetrahydrobenzo[d][1,3]dioxole-3a-carboxylate

(3aS,4R,7S,7aR)-benzyl 7-(benzyloxycarbonylamino)-2,2-dimethyl-4-(4-nitrobenzoyloxy)-3a,4,7,7a-tetrahydrobenzo[d][1,3]dioxole-3a-carboxylate