(1R,3S,4S)-(4-benzyloxycarbonylamino-3-propenylcyclohexyl)carbamic acid tert-butyl ester

Base Information

• Chemical Name: (1R,3S,4S)-(4-benzyloxycarbonylamino-3-propenylcyclohexyl)carbamic acid tert-butyl ester
• CAS No.: 847956-53-0
• Molecular Formula: C₂₂H₃₂N₂O₄
• Molecular Weight: 388.507

Synonyms:(1R,3S,4S)-(4-benzyloxycarbonylamino-3-propenylcyclohexyl)carbamic acid tert-butyl ester

Chemical Property of (1R,3S,4S)-(4-benzyloxycarbonylamino-3-propenylcyclohexyl)carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3S,4S)-(4-benzyloxycarbonylamino-3-propenylcyclohexyl)carbamic acid tert-butyl ester

There total 2 articles about (1R,3S,4S)-(4-benzyloxycarbonylamino-3-propenylcyclohexyl)carbamic acid tert-butyl ester 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:

tert-butyl (1R,2S,5R,7R/S)-2-(benzyloxycarbonylamino)-7-hydroxy-6-aza-bicyclo[3.2.1]octane-6-carboxylate (847955-78-6) + ethyltriphenylphosphonium iodide (4736-60-1) → (1R,3S,4S)-(4-benzyloxycarbonylamino-3-propenylcyclohexyl)carbamic acid tert-butyl ester (847956-53-0)

Guidance literature:

ethyltriphenylphosphonium iodide; With potassium hexamethylsilazane; In toluene; at 0 ℃; for 0.25h;

tert-butyl (1R,2S,5R,7R/S)-2-(benzyloxycarbonylamino)-7-hydroxy-6-aza-bicyclo[3.2.1]octane-6-carboxylate; In tetrahydrofuran; toluene; at 0 ℃; for 0.416667h;

Reference yield:

(1R,2S,5R)-tert-butyl 2-(benzyloxycarbonylamino)-7-oxo-6-azabicyclo[3.2.1]octane-6-carboxylate (746670-91-7) → (1R,3S,4S)-(4-benzyloxycarbonylamino-3-propenylcyclohexyl)carbamic acid tert-butyl ester (847956-53-0)

Guidance literature:

Multi-step reaction with 2 steps

1: diisobutylaluminium hydride / dichloromethane; tetrahydrofuran / 1.75 h / 0 °C

2: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.42 h / 0 °C

With potassium hexamethylsilazane; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/ml500505q

Reference yield: 100.0%

(1R,3S,4S)-(4-benzyloxycarbonylamino-3-propenylcyclohexyl)carbamic acid tert-butyl ester (847956-53-0) → (1R,3R,4S)-(4-amino-3-propyl-cyclohexyl)carbamic acid tert-butyl ester (847956-54-1)

Guidance literature:

With hydrogen; 5% palladium-on-charcoal; In methanol; for 4h; under 760.051 Torr;

upstream raw materials:

tert-butyl (1R,2S,5R,7R/S)-2-(benzyloxycarbonylamino)-7-hydroxy-6-aza-bicyclo[3.2.1]octane-6-carboxylate

ethyltriphenylphosphonium iodide

(1R,2S,5R)-tert-butyl 2-(benzyloxycarbonylamino)-7-oxo-6-azabicyclo[3.2.1]octane-6-carboxylate

Downstream raw materials:

(1R,3R,4S)-(4-amino-3-propyl-cyclohexyl)carbamic acid tert-butyl ester

(1R,3R,4S)-[4-((2S)-2-benzyloxycarbonylamino-4-methylsulfanylbutyrylamino)-3-propylcyclohexyl]carbamic acid tert-butyl ester

C₂₈H₄₆N₃O₅S⁽¹⁺⁾*I^(1-)

{(3S)-1-[(1S,2R,4R)-4-tert-butoxycarbonylamino-2-propylcyclohexyl]-2-oxopyrrolidin-3-yl}carbamic acid benzyl ester

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