benzyl N-[2-[(5aR,6R,9aS)-6-(tert-butyldimethylsilyloxy)-6,7-dihydro-1-(2,2-dimethoxyethyl)-4-methoxy-9a(5aH)-dibenzofuranyl]ethyl]carbamate

Base Information

• Chemical Name: benzyl N-[2-[(5aR,6R,9aS)-6-(tert-butyldimethylsilyloxy)-6,7-dihydro-1-(2,2-dimethoxyethyl)-4-methoxy-9a(5aH)-dibenzofuranyl]ethyl]carbamate
• CAS No.: 1201905-44-3
• Molecular Formula: C₃₃H₄₇NO₇Si
• Molecular Weight: 597.824
• Mol file: 1201905-44-3.mol

Synonyms:benzyl N-[2-[(5aR,6R,9aS)-6-(tert-butyldimethylsilyloxy)-6,7-dihydro-1-(2,2-dimethoxyethyl)-4-methoxy-9a(5aH)-dibenzofuranyl]ethyl]carbamate

Chemical Property of benzyl N-[2-[(5aR,6R,9aS)-6-(tert-butyldimethylsilyloxy)-6,7-dihydro-1-(2,2-dimethoxyethyl)-4-methoxy-9a(5aH)-dibenzofuranyl]ethyl]carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl N-[2-[(5aR,6R,9aS)-6-(tert-butyldimethylsilyloxy)-6,7-dihydro-1-(2,2-dimethoxyethyl)-4-methoxy-9a(5aH)-dibenzofuranyl]ethyl]carbamate

There total 11 articles about benzyl N-[2-[(5aR,6R,9aS)-6-(tert-butyldimethylsilyloxy)-6,7-dihydro-1-(2,2-dimethoxyethyl)-4-methoxy-9a(5aH)-dibenzofuranyl]ethyl]carbamate 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: 96.0%

benzyl 2-((5R,6R)-5-(tert-butyldimethylsilyloxy)-6-(3-(2,2-dimethoxyethyl)-2-iodo-6-methoxyphenoxy)cyclohex-1-enyl)ethylcarbamate (1257051-27-6) → benzyl N-[2-[(5aR,6R,9aS)-6-(tert-butyldimethylsilyloxy)-6,7-dihydro-1-(2,2-dimethoxyethyl)-4-methoxy-9a(5aH)-dibenzofuranyl]ethyl]carbamate (1201905-44-3)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; triethylamine; tris-(o-tolyl)phosphine; In acetonitrile; at 85 ℃; for 1h;

DOI:10.1002/asia.201000458

Reference yield:

2-iodo-4-methoxy-3-(methoxymethoxy)-1-(2-methoxyvinyl)benzene → benzyl N-[2-[(5aR,6R,9aS)-6-(tert-butyldimethylsilyloxy)-6,7-dihydro-1-(2,2-dimethoxyethyl)-4-methoxy-9a(5aH)-dibenzofuranyl]ethyl]carbamate (1201905-44-3)

Guidance literature:

Multi-step reaction with 3 steps

1: acetyl chloride / methanol / 1 h / 40 °C

2: tributylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 0.5 h / 20 °C

3: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; triethylamine; tris-(o-tolyl)phosphine / acetonitrile / 1 h / 85 °C

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tributylphosphine; triethylamine; acetyl chloride; tris-(o-tolyl)phosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; toluene; acetonitrile; 2: Mitsunobu reaction / 3: Heck reaction;

DOI:10.1002/asia.201000458

Reference yield:

2-iodo-6-methoxy-3-(2,2-dimethoxyethyl)phenol (916225-97-3) → benzyl N-[2-[(5aR,6R,9aS)-6-(tert-butyldimethylsilyloxy)-6,7-dihydro-1-(2,2-dimethoxyethyl)-4-methoxy-9a(5aH)-dibenzofuranyl]ethyl]carbamate (1201905-44-3)

Guidance literature:

Multi-step reaction with 2 steps

1: tributylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 0.5 h / 20 °C

2: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; triethylamine; tris-(o-tolyl)phosphine / acetonitrile / 1 h / 85 °C

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tributylphosphine; triethylamine; tris-(o-tolyl)phosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; acetonitrile; 1: Mitsunobu reaction / 2: Heck reaction;

DOI:10.1002/asia.201000458

upstream raw materials:

2-iodo-6-methoxy-3-(2,2-dimethoxyethyl)phenol

cyclohexenone

(1R,6R)-6-(tert-butyldimethylsilyloxy)-2-iodocyclohex-2-enol

benzyl 2-((5R,6S)-5-(tert-butyldimethylsilyloxy)-6-hydroxycyclohex-1-enyl)ethylcarbamate

Downstream raw materials:

N-[2-[(5aR,6R,9aS)-6,7-dihydro-6-hydroxy-1-(2,2-dimethoxyethyl)-4-methoxy-9a(5aH)-dibenzofuranyl]ethyl]-N-methyl-2,4-dinitrobenzenesulfonamide

N-[2-[(5aR,9aS)-6,7-dihydro-1-(2,2-dimethoxyethyl)-4-methoxy-6-oxo-9a(5aH)-dibenzofuranyl]ethyl]-N-methyl-2,4-dinitrobenzenesulfonamide

C₂₄H₂₃N₃O₁₀S

C₂₄H₂₁N₃O₉S