(E)-N-(((1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)carbamoyl)-3-methoxy-2-methylacrylamide

Base Information

• Chemical Name: (E)-N-(((1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)carbamoyl)-3-methoxy-2-methylacrylamide
• CAS No.: 1345024-31-8
• Molecular Formula: C₂₈H₃₆N₂O₅Si
• Molecular Weight: 508.69
• Mol file: 1345024-31-8.mol

Synonyms:

Chemical Property of (E)-N-(((1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)carbamoyl)-3-methoxy-2-methylacrylamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-N-(((1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)carbamoyl)-3-methoxy-2-methylacrylamide

There total 12 articles about (E)-N-(((1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)carbamoyl)-3-methoxy-2-methylacrylamide 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: 41.0%

C23H27NO3Si + (E)-3-methoxy-2-methylacrylamide → (E)-N-(((1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)carbamoyl)-3-methoxy-2-methylacrylamide (1345024-31-8)

Guidance literature:

(E)-3-methoxy-2-methylacrylamide; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

C₂₃H₂₇NO₃Si; In tetrahydrofuran; hexane; toluene; at -78 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/jo201716c

Reference yield:

tert-Butyl-[(R)-1-(2,3-dihydro-furan-3-yl)methoxy]-diphenyl-silane (287933-72-6) → (E)-N-(((1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)carbamoyl)-3-methoxy-2-methylacrylamide (1345024-31-8)

Guidance literature:

Multi-step reaction with 11 steps

1.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / acetone; tert-butyl alcohol / Inert atmosphere

2.1: pyridine / dichloromethane / Inert atmosphere

3.1: boron trifluoride diethyl etherate / acetonitrile / 0.5 h / 0 - 20 °C / Inert atmosphere

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 96 h / Inert atmosphere

5.1: sodium hydride / mineral oil / 0 - 20 °C / Inert atmosphere

5.2: 20 °C / Inert atmosphere

6.1: diisobutylaluminium hydride / toluene / 0.5 h / -78 - 20 °C / Inert atmosphere

6.2: 20 °C / Inert atmosphere

7.1: diethylzinc / dichloromethane; toluene / 1 h / 0 - 20 °C / Inert atmosphere

8.1: sodium periodate; ruthenium trichloride; sodium hydrogencarbonate / chloroform; water; acetonitrile / 20 °C / Inert atmosphere

8.2: 20 °C / Inert atmosphere

9.1: diphenyl phosphoryl azide; triethylamine / toluene / 2 h / 0 - 20 °C / Inert atmosphere

10.1: toluene / 2 h / 80 °C / Inert atmosphere

11.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

11.2: 0.5 h / -78 °C / Inert atmosphere

With pyridine; ruthenium trichloride; sodium periodate; osmium(VIII) oxide; n-butyllithium; diphenyl phosphoryl azide; boron trifluoride diethyl etherate; diethylzinc; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; hexane; dichloromethane; chloroform; water; acetone; toluene; acetonitrile; mineral oil; tert-butyl alcohol; 7.1: Simmons-Smith reaction / 10.1: Curtius rearrangement;

DOI:10.1021/jo201716c

Reference yield:

(2S,3R,4R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-cyanotetrahydrofuran-3-yl acetate (1345023-89-3) → (E)-N-(((1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)carbamoyl)-3-methoxy-2-methylacrylamide (1345024-31-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: methanol; sodium hydride / mineral oil / 0.25 h / 0 °C / Inert atmosphere

1.2: 0 °C / Inert atmosphere

2.1: triethylamine / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 20 °C / Inert atmosphere

4.1: sodium hydride / mineral oil / 0 - 20 °C / Inert atmosphere

4.2: 20 °C / Inert atmosphere

5.1: diisobutylaluminium hydride / toluene / 0.5 h / -78 - 20 °C / Inert atmosphere

5.2: 20 °C / Inert atmosphere

6.1: diethylzinc / dichloromethane; toluene / 1 h / 0 - 20 °C / Inert atmosphere

7.1: sodium periodate; ruthenium trichloride; sodium hydrogencarbonate / chloroform; water; acetonitrile / 20 °C / Inert atmosphere

7.2: 20 °C / Inert atmosphere

8.1: diphenyl phosphoryl azide; triethylamine / toluene / 2 h / 0 - 20 °C / Inert atmosphere

9.1: toluene / 2 h / 80 °C / Inert atmosphere

10.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

10.2: 0.5 h / -78 °C / Inert atmosphere

With methanol; ruthenium trichloride; sodium periodate; n-butyllithium; diphenyl phosphoryl azide; diethylzinc; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; hexane; dichloromethane; chloroform; water; toluene; acetonitrile; mineral oil; 6.1: Simmons-Smith reaction / 9.1: Curtius rearrangement;

DOI:10.1021/jo201716c

upstream raw materials:

(2S,3R,4R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-cyanotetrahydrofuran-3-yl acetate

(2S,3R,4R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-3-hydroxytetrahydrofuran-2-carbonitrile

(R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-4,5-dihydrofuran-2-carbonitrile

((1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)methanol

Downstream raw materials:

C₂₇H₃₂N₂O₄Si