[2-benzyloxymethyl-5-(tert-butoxycarbonylaminomethyl)cyclopentyl]carbamic acid benzyl ester

Base Information

Chemical Name:[2-benzyloxymethyl-5-(tert-butoxycarbonylaminomethyl)cyclopentyl]carbamic acid benzyl ester
CAS No.:476371-51-4
Molecular Formula:C₂₇H₃₆N₂O₅
Molecular Weight:468.593
Hs Code.:

Synonyms:[2-benzyloxymethyl-5-(tert-butoxycarbonylaminomethyl)cyclopentyl]carbamic acid benzyl ester

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Chemical Property of [2-benzyloxymethyl-5-(tert-butoxycarbonylaminomethyl)cyclopentyl]carbamic acid benzyl ester

Chemical Property:

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Technology Process of [2-benzyloxymethyl-5-(tert-butoxycarbonylaminomethyl)cyclopentyl]carbamic acid benzyl ester

There total 11 articles about [2-benzyloxymethyl-5-(tert-butoxycarbonylaminomethyl)cyclopentyl]carbamic acid benzyl 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:

: 24424-99-5
di-tert-butyl dicarbonate

: ((1R,2R,5R)-2-Aminomethyl-5-benzyloxymethyl-cyclopentyl)-carbamic acid benzyl ester

: 476371-51-4
[2-benzyloxymethyl-5-(tert-butoxycarbonylaminomethyl)cyclopentyl]carbamic acid benzyl ester

Guidance literature:: With triethylamine; In methanol; at 20 ℃; for 24h;
DOI:10.1021/ja0258778

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 476371-51-4
[2-benzyloxymethyl-5-(tert-butoxycarbonylaminomethyl)cyclopentyl]carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: tetrahydrofuran; dimethylformamide / 0.25 h / -40 °C

1.2: (+)-IPC₂BH / tetrahydrofuran / 48 h / -10 °C

1.3: 73 percent / aq. H₂O₂; NaOH / 12 h / 20 °C

2.1: 83 percent / pyridine / 12 h / 20 °C

3.1: 77 percent / LAH / diethyl ether / 20 h / Heating

4.1: 85 percent / tert-butyl hydroperoxide; TiCl₄ / CH₂Cl₂; various solvent(s) / 0.25 h / -78 °C

5.1: NaN₃; aq. NH₄Cl / methanol / 15 h / Heating

5.2: methane sulfonyl chloride; pyridine / 2 h / 20 °C

5.3: 84 percent / LAH / tetrahydrofuran / 5 h / 20 °C

6.1: 93 percent / Et₃N / CH₂Cl₂ / 2 h / 20 °C

7.1: 90 percent / NH₄Cl; 18-crown-6 / dimethylsulfoxide / 6 h / 80 °C

8.1: BH₃*THF / tetrahydrofuran / 5 h / 20 °C

9.1: 4.55 g / Et₃N / methanol / 24 h / 20 °C

With pyridine; tert.-butylhydroperoxide; lithium aluminium tetrahydride; sodium azide; borane-THF; 18-crown-6 ether; titanium tetrachloride; ammonium chloride; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/ja0258778

Reference yield:

: 110567-21-0
(1S,2R)-2-(benzyloxymethyl)-1-hydroxy-3-cyclopentene

: 476371-51-4
[2-benzyloxymethyl-5-(tert-butoxycarbonylaminomethyl)cyclopentyl]carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 83 percent / pyridine / 12 h / 20 °C

2.1: 77 percent / LAH / diethyl ether / 20 h / Heating

3.1: 85 percent / tert-butyl hydroperoxide; TiCl₄ / CH₂Cl₂; various solvent(s) / 0.25 h / -78 °C

4.1: NaN₃; aq. NH₄Cl / methanol / 15 h / Heating

4.2: methane sulfonyl chloride; pyridine / 2 h / 20 °C

4.3: 84 percent / LAH / tetrahydrofuran / 5 h / 20 °C

5.1: 93 percent / Et₃N / CH₂Cl₂ / 2 h / 20 °C

6.1: 90 percent / NH₄Cl; 18-crown-6 / dimethylsulfoxide / 6 h / 80 °C

7.1: BH₃*THF / tetrahydrofuran / 5 h / 20 °C

8.1: 4.55 g / Et₃N / methanol / 24 h / 20 °C

With pyridine; tert.-butylhydroperoxide; lithium aluminium tetrahydride; sodium azide; borane-THF; 18-crown-6 ether; titanium tetrachloride; ammonium chloride; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide;
DOI:10.1021/ja0258778