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

Base Information

• Chemical Name: 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
• CAS No.: 1449329-22-9
• Molecular Formula: C₄₂H₆₁N₃O₇Si₂
• Molecular Weight: 776.133
• Mol file: 1449329-22-9.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 19 articles about 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 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: 75.0%

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 (1449329-21-8) + methylmagnesium bromide (75-16-1) → 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 (1449329-22-9)

Guidance literature:

In tetrahydrofuran; at 0 ℃;

DOI:10.1126/science.1234756

Reference yield:

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) → 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 (1449329-22-9)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine; dmap / dichloromethane / 0 - 20 °C

2: tetrahydrofuran / 0 °C

With dmap; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1126/science.1234756

Reference yield:

3-(2,4-dioxopentan-3-yl)-1,1-dimethylurea (1449329-12-7) → 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 (1449329-22-9)

Guidance literature:

Multi-step reaction with 9 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

8.1: triethylamine; dmap / dichloromethane / 0 - 20 °C

9.1: tetrahydrofuran / 0 °C

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

DOI:10.1126/science.1234756

upstream 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

methylmagnesium bromide

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

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

Downstream raw materials:

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

((1S,2R,3R,4S,5S)-5-((3-acetylphenyl)amino)-4-(((benzyloxy)carbonyl)amino)-3-(3,3-dimethylureido)-1,2-dihydroxy-3-((S)-1-hydroxyethyl)-2-methylcyclopentyl)methyl 2-hydroxy-6-methylbenzoate

pactamycin

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