((E)-(S)-2-Benzyloxy-7-hydroxy-hept-5-enyl)-carbamic acid tert-butyl ester

Base Information

Chemical Name:((E)-(S)-2-Benzyloxy-7-hydroxy-hept-5-enyl)-carbamic acid tert-butyl ester
CAS No.:188409-92-9
Molecular Formula:C₁₉H₂₉NO₄
Molecular Weight:335.444
Hs Code.:

Synonyms:((E)-(S)-2-Benzyloxy-7-hydroxy-hept-5-enyl)-carbamic acid tert-butyl ester

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Chemical Property of ((E)-(S)-2-Benzyloxy-7-hydroxy-hept-5-enyl)-carbamic acid tert-butyl ester

Chemical Property:

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Technology Process of ((E)-(S)-2-Benzyloxy-7-hydroxy-hept-5-enyl)-carbamic acid tert-butyl ester

There total 11 articles about ((E)-(S)-2-Benzyloxy-7-hydroxy-hept-5-enyl)-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: 95.0%

: 188410-06-2
(E)-(S)-6-Benzyloxy-7-tert-butoxycarbonylamino-hept-2-enoic acid methyl ester

: 188409-92-9
((E)-(S)-2-Benzyloxy-7-hydroxy-hept-5-enyl)-carbamic acid tert-butyl ester

Guidance literature:: With diisobutylaluminium hydride; In tetrahydrofuran; at -78 ℃;
DOI:10.1246/cl.1997.221

Reference yield:

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

: 188409-92-9
((E)-(S)-2-Benzyloxy-7-hydroxy-hept-5-enyl)-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 70 percent / Et₃N / CH₂Cl₂

2: 84 percent / (COCl₂)2, DMSO, Et₃N / CH₂Cl₂

3: 68 percent / CH₂Cl₂

4: 97 percent / H₂ / Pd-C / ethyl acetate

5: 79 percent / DIBAL / tetrahydrofuran / -78 °C

6: 98 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂

7: 91 percent / benzene / Heating

8: 95 percent / DIBAL / tetrahydrofuran / -78 °C

With oxalyl dichloride; (COCl₂)2; hydrogen; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; benzene;
DOI:10.1246/cl.1997.221

Reference yield:

: 100-39-0
benzyl bromide

: 188409-92-9
((E)-(S)-2-Benzyloxy-7-hydroxy-hept-5-enyl)-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 94 percent / NaH, Bu₄NI / tetrahydrofuran

2: 76 percent / LiAlH₄ / diethyl ether

3: 70 percent / Et₃N / CH₂Cl₂

4: 84 percent / (COCl₂)2, DMSO, Et₃N / CH₂Cl₂

5: 68 percent / CH₂Cl₂

6: 97 percent / H₂ / Pd-C / ethyl acetate

7: 79 percent / DIBAL / tetrahydrofuran / -78 °C

8: 98 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂

9: 91 percent / benzene / Heating

10: 95 percent / DIBAL / tetrahydrofuran / -78 °C

With lithium aluminium tetrahydride; oxalyl dichloride; (COCl₂)2; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; benzene;
DOI:10.1246/cl.1997.221