methyl (E)-5-benzyloxy-2-[(tert-butoxycarbonyl)amino]pent-3-enoate

Base Information

• Chemical Name: methyl (E)-5-benzyloxy-2-[(tert-butoxycarbonyl)amino]pent-3-enoate
• CAS No.: 1307905-20-9
• Molecular Formula: C₁₈H₂₅NO₅
• Molecular Weight: 335.4
• Mol file: 1307905-20-9.mol

Synonyms:

Chemical Property of methyl (E)-5-benzyloxy-2-[(tert-butoxycarbonyl)amino]pent-3-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (E)-5-benzyloxy-2-[(tert-butoxycarbonyl)amino]pent-3-enoate

There total 10 articles about methyl (E)-5-benzyloxy-2-[(tert-butoxycarbonyl)amino]pent-3-enoate 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:

5-benzyloxypent-2-yne-1,4-diol (1307905-31-2) → methyl (E)-5-benzyloxy-2-[(tert-butoxycarbonyl)amino]pent-3-enoate (1307905-20-9)

Guidance literature:

Multi-step reaction with 7 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 2.5 h / 0 °C / Inert atmosphere; Molecular sieve

3: iron(III) chloride / dichloromethane / 0.08 h / 20 °C / Inert atmosphere; Molecular sieve

4: hydrogenchloride / ethanol; water / 20 °C / Inert atmosphere; Reflux

5: sodium hydrogencarbonate / water; ethyl acetate / 20 °C / Inert atmosphere

6: Jones reagent / acetone / Inert atmosphere; Cooling with ice

7: tetrahydrofuran; diethyl ether / Inert atmosphere; Cooling with ice

With hydrogenchloride; iron(III) chloride; lithium aluminium tetrahydride; Jones reagent; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; acetone;

DOI:10.1002/ejoc.201100060

Reference yield:

benzyloxyacetoaldehyde (60656-87-3) → methyl (E)-5-benzyloxy-2-[(tert-butoxycarbonyl)amino]pent-3-enoate (1307905-20-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 2.5 h / 0 °C / Inert atmosphere; Molecular sieve

4.1: iron(III) chloride / dichloromethane / 0.08 h / 20 °C / Inert atmosphere; Molecular sieve

5.1: hydrogenchloride / ethanol; water / 20 °C / Inert atmosphere; Reflux

6.1: sodium hydrogencarbonate / water; ethyl acetate / 20 °C / Inert atmosphere

7.1: Jones reagent / acetone / Inert atmosphere; Cooling with ice

8.1: tetrahydrofuran; diethyl ether / Inert atmosphere; Cooling with ice

With hydrogenchloride; iron(III) chloride; lithium aluminium tetrahydride; Jones reagent; n-butyllithium; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; ethyl acetate; acetone;

DOI:10.1002/ejoc.201100060

Reference yield:

2,2,2-trichloroacetimidic acid (Z)-1-benzyloxymethyl-4-(2,2,2-trichloroacetimidoyloxy)but-2-enyl ester (1307904-91-1) → methyl (E)-5-benzyloxy-2-[(tert-butoxycarbonyl)amino]pent-3-enoate (1307905-20-9)

Guidance literature:

Multi-step reaction with 5 steps

1: boron trifluoride diethyl etherate / dichloromethane / 0.02 h / 20 °C / Inert atmosphere; Molecular sieve

2: hydrogenchloride / ethanol; water / 20 °C / Inert atmosphere; Reflux

3: sodium hydrogencarbonate / water; ethyl acetate / 20 °C / Inert atmosphere

4: Jones reagent / acetone / Inert atmosphere; Cooling with ice

5: tetrahydrofuran; diethyl ether / Inert atmosphere; Cooling with ice

With hydrogenchloride; Jones reagent; boron trifluoride diethyl etherate; sodium hydrogencarbonate; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; acetone;

DOI:10.1002/ejoc.201100060

upstream raw materials:

Diazoethan

(E)-4-(3-benzyloxyprop-1-en-1-yl)-2-(trichloromethyl)-4,5-dihydro-1,3-oxazole

(E)-5-benzyloxy-2-[(tert-butoxycarbonyl)amino]pent-3-en-1-ol

5-benzyloxypent-2-yne-1,4-diol