N-[2-(tert-butyl-dimethyl-silanyloxy)-4,4-dimethyl-hexahydro-1,3,5-trioxa-cyclopropa[f]inden-6-yl]-N-(4-methoxy-benzo[1,3]dioxol-5-ylmethyl)-4-nitro-benzenesulfonamide

Base Information

• Chemical Name: N-[2-(tert-butyl-dimethyl-silanyloxy)-4,4-dimethyl-hexahydro-1,3,5-trioxa-cyclopropa[f]inden-6-yl]-N-(4-methoxy-benzo[1,3]dioxol-5-ylmethyl)-4-nitro-benzenesulfonamide
• CAS No.: 474526-66-4
• Molecular Formula: C₃₀H₄₀N₂O₁₁SSi
• Molecular Weight: 664.806
• Mol file: 474526-66-4.mol

Synonyms:N-[2-(tert-butyl-dimethyl-silanyloxy)-4,4-dimethyl-hexahydro-1,3,5-trioxa-cyclopropa[f]inden-6-yl]-N-(4-methoxy-benzo[1,3]dioxol-5-ylmethyl)-4-nitro-benzenesulfonamide

Chemical Property of N-[2-(tert-butyl-dimethyl-silanyloxy)-4,4-dimethyl-hexahydro-1,3,5-trioxa-cyclopropa[f]inden-6-yl]-N-(4-methoxy-benzo[1,3]dioxol-5-ylmethyl)-4-nitro-benzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[2-(tert-butyl-dimethyl-silanyloxy)-4,4-dimethyl-hexahydro-1,3,5-trioxa-cyclopropa[f]inden-6-yl]-N-(4-methoxy-benzo[1,3]dioxol-5-ylmethyl)-4-nitro-benzenesulfonamide

There total 5 articles about N-[2-(tert-butyl-dimethyl-silanyloxy)-4,4-dimethyl-hexahydro-1,3,5-trioxa-cyclopropa[f]inden-6-yl]-N-(4-methoxy-benzo[1,3]dioxol-5-ylmethyl)-4-nitro-benzenesulfonamide 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: 91.0%

5-Bromomethyl-4-methoxy-benzo[1,3]dioxole (474526-68-6) + (1S,2S,3S,6R)-3-((t-butyldimethylsilyl)oxy)-1,2-O-isopropylidene-6-(N-(p-nitrobenzenesulfonyl)amino)cyclohexene-1,2-diol (474526-55-1) → N-[2-(tert-butyl-dimethyl-silanyloxy)-4,4-dimethyl-hexahydro-1,3,5-trioxa-cyclopropa[f]inden-6-yl]-N-(4-methoxy-benzo[1,3]dioxol-5-ylmethyl)-4-nitro-benzenesulfonamide (474526-66-4)

Guidance literature:

(1S,2S,3S,6R)-3-((t-butyldimethylsilyl)oxy)-1,2-O-isopropylidene-6-(N-(p-nitrobenzenesulfonyl)amino)cyclohexene-1,2-diol; With N-Bromosuccinimide; In water; acetone; at 20 ℃; for 10h;

5-Bromomethyl-4-methoxy-benzo[1,3]dioxole; With potassium carbonate; In acetonitrile; at 60 ℃; Further stages.;

DOI:10.1021/jo020155k

Reference yield:

2-methoxy-3,4-methylenedioxybenzyl alcohol (108261-13-8) → N-[2-(tert-butyl-dimethyl-silanyloxy)-4,4-dimethyl-hexahydro-1,3,5-trioxa-cyclopropa[f]inden-6-yl]-N-(4-methoxy-benzo[1,3]dioxol-5-ylmethyl)-4-nitro-benzenesulfonamide (474526-66-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 96 percent / HBr / CH₂Cl₂; H₂O / 25 °C

2.1: NBS / H₂O; acetone / 10 h / 20 °C

2.2: 91 percent / K₂CO₃ / acetonitrile / 60 °C

With N-Bromosuccinimide; hydrogen bromide; In dichloromethane; water; acetone;

DOI:10.1021/jo020155k

Reference yield:

cis-2,2-dimethyl-3a,7a-dihydrobenzo[1,3]dioxole (80409-75-2,343865-40-7) → N-[2-(tert-butyl-dimethyl-silanyloxy)-4,4-dimethyl-hexahydro-1,3,5-trioxa-cyclopropa[f]inden-6-yl]-N-(4-methoxy-benzo[1,3]dioxol-5-ylmethyl)-4-nitro-benzenesulfonamide (474526-66-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: chiral chloronitroso synthon / CH₂Cl₂ / 12 h / 0 °C

1.2: 85 percent / Al-Hg / acetonitrile; H₂O / 1.5 h / 20 °C

2.1: Et₃N / acetonitrile / 8 h / 25 °C

3.1: 3.78 g / DBU / acetonitrile / 9 h / 25 °C

4.1: NBS / H₂O; acetone / 10 h / 20 °C

4.2: 91 percent / K₂CO₃ / acetonitrile / 60 °C

With N-Bromosuccinimide; chiral chloronitroso synthon; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In dichloromethane; water; acetone; acetonitrile;

DOI:10.1021/jo020155k

upstream raw materials:

5-Bromomethyl-4-methoxy-benzo[1,3]dioxole

(1S,2S,3S,6R)-3-((t-butyldimethylsilyl)oxy)-1,2-O-isopropylidene-6-(N-(p-nitrobenzenesulfonyl)amino)cyclohexene-1,2-diol

2-methoxy-3,4-methylenedioxybenzyl alcohol

cis-2,2-dimethyl-3a,7a-dihydrobenzo[1,3]dioxole