benzyl ((1R,2R,3R,5R)-3-((S)-1-((tert-butyldimethylsilyl)oxy)ethyl)-3-(3,3-dimethylureido)-5-(hydroxymethyl)-4-oxo-6-oxabicyclo[3.1.0]hexan-2-yl)carbamate

Base Information

• Chemical Name: benzyl ((1R,2R,3R,5R)-3-((S)-1-((tert-butyldimethylsilyl)oxy)ethyl)-3-(3,3-dimethylureido)-5-(hydroxymethyl)-4-oxo-6-oxabicyclo[3.1.0]hexan-2-yl)carbamate
• CAS No.: 1449329-20-7
• Molecular Formula: C₂₅H₃₉N₃O₇Si
• Molecular Weight: 521.686
• Mol file: 1449329-20-7.mol

Synonyms:benzyl ((1R,2R,3R,5R)-3-((S)-1-((tert-butyldimethylsilyl)oxy)ethyl)-3-(3,3-dimethylureido)-5-(hydroxymethyl)-4-oxo-6-oxabicyclo[3.1.0]hexan-2-yl)carbamate

Chemical Property of benzyl ((1R,2R,3R,5R)-3-((S)-1-((tert-butyldimethylsilyl)oxy)ethyl)-3-(3,3-dimethylureido)-5-(hydroxymethyl)-4-oxo-6-oxabicyclo[3.1.0]hexan-2-yl)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl ((1R,2R,3R,5R)-3-((S)-1-((tert-butyldimethylsilyl)oxy)ethyl)-3-(3,3-dimethylureido)-5-(hydroxymethyl)-4-oxo-6-oxabicyclo[3.1.0]hexan-2-yl)carbamate

There total 18 articles about benzyl ((1R,2R,3R,5R)-3-((S)-1-((tert-butyldimethylsilyl)oxy)ethyl)-3-(3,3-dimethylureido)-5-(hydroxymethyl)-4-oxo-6-oxabicyclo[3.1.0]hexan-2-yl)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: 81.0%

benzyl ((1S,5R)-5-((S)-1-((tert-butyldimethylsilyl)oxy)ethyl)-5-(3,3-dimethylureido)-3-(hydroxymethyl)-4-oxocyclopent-2-en-1-yl)carbamate → benzyl ((1R,2R,3R,5R)-3-((S)-1-((tert-butyldimethylsilyl)oxy)ethyl)-3-(3,3-dimethylureido)-5-(hydroxymethyl)-4-oxo-6-oxabicyclo[3.1.0]hexan-2-yl)carbamate (1449329-20-7)

Guidance literature:

With dihydrogen peroxide; In methanol; dichloromethane; water; at 0 ℃; for 2h; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/ja409944u

Reference yield: 81.0%

C25H39N3O6Si → benzyl ((1R,2R,3R,5R)-3-((S)-1-((tert-butyldimethylsilyl)oxy)ethyl)-3-(3,3-dimethylureido)-5-(hydroxymethyl)-4-oxo-6-oxabicyclo[3.1.0]hexan-2-yl)carbamate (1449329-20-7)

Guidance literature:

With dihydrogen peroxide; sodium hydroxide; In methanol; dichloromethane; at 0 ℃;

DOI:10.1126/science.1234756

Reference yield:

3-(2,4-dioxopentan-3-yl)-1,1-dimethylurea (1449329-12-7) → benzyl ((1R,2R,3R,5R)-3-((S)-1-((tert-butyldimethylsilyl)oxy)ethyl)-3-(3,3-dimethylureido)-5-(hydroxymethyl)-4-oxo-6-oxabicyclo[3.1.0]hexan-2-yl)carbamate (1449329-20-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: (-)-cinchonidine / dichloromethane / -65 °C

2.1: lithium tri-(tert-butoxy)aluminum hydride / tetrahydrofuran / -40 °C

3.1: 2,6-dimethylpyridine / dichloromethane / -78 °C

4.1: lithium diisopropyl amide / tetrahydrofuran / -78 - -45 °C

5.1: ozone / dichloromethane / -78 °C

5.2: -78 - 20 °C

6.1: sodium methylate / tetrahydrofuran / 0 °C

7.1: dihydrogen peroxide; sodium hydroxide / dichloromethane; methanol / 0 °C

With 2,6-dimethylpyridine; dihydrogen peroxide; sodium methylate; (-)-cinchonidine; ozone; lithium tri-(tert-butoxy)aluminum hydride; sodium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; 1.1: |Mannich Aminomethylation;

DOI:10.1126/science.1234756

upstream raw materials:

3-(2,4-dioxopentan-3-yl)-1,1-dimethylurea

[(E)-3-Phenyl-prop-2-en-(E)-ylidene]-carbamic acid benzyl ester

C₂₅H₄₁N₃O₇Si

acetylacetone

Downstream raw materials:

benzyl ((1R,2R,3R,5R)-3-((S)-1-((tert-butyldimethylsilyl)oxy)ethyl)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-3-(3,3-dimethylureido)-4-oxo-6-oxabicyclo[3.1.0] hexan2-yl)carbamate

benzyl ((1R,2R,3R,4R,5R)-3-((S)-1-((tert-butyldimethylsilyl)oxy)ethyl)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-3-(3,3-dimethylureido)-4-hydroxy-4-methyl-6-oxabicyclo[3.1.0]hexan-2-yl)carbamate

benzyl ((1S,2R,3R,4S,5S)-5-((3-acetylphenyl)amino)-2-((S)-1-((tert-butyldimethylsilyl)oxy)ethyl)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-(3,3 dimethylureido)-3,4-dihydroxy-3-methylcyclopentyl)carbamate

benzyl ((1S,2R,3R,4S,5S)-5-((3-acetylphenyl)amino)-2-(3,3-dimethylureido)-3,4-dihydroxy-2-((S)-1-hydroxyethyl)-4-(hydroxymethyl)-3-methylcyclopentyl)carbamate