benzyl {(R)-6-tert-butoxycarbonylamino-2-[(3aS,7aS)-2-oxooctahydrobenzo[d]oxazole-3-carbonyl]-hexyl}carbamate

Base Information

Chemical Name:benzyl {(R)-6-tert-butoxycarbonylamino-2-[(3aS,7aS)-2-oxooctahydrobenzo[d]oxazole-3-carbonyl]-hexyl}carbamate
CAS No.:1605314-26-8
Molecular Formula:C₂₇H₃₉N₃O₇
Molecular Weight:517.623
Hs Code.:

Synonyms:benzyl {(R)-6-tert-butoxycarbonylamino-2-[(3aS,7aS)-2-oxooctahydrobenzo[d]oxazole-3-carbonyl]-hexyl}carbamate

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Chemical Property of benzyl {(R)-6-tert-butoxycarbonylamino-2-[(3aS,7aS)-2-oxooctahydrobenzo[d]oxazole-3-carbonyl]-hexyl}carbamate

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Technology Process of benzyl {(R)-6-tert-butoxycarbonylamino-2-[(3aS,7aS)-2-oxooctahydrobenzo[d]oxazole-3-carbonyl]-hexyl}carbamate

There total 5 articles about benzyl {(R)-6-tert-butoxycarbonylamino-2-[(3aS,7aS)-2-oxooctahydrobenzo[d]oxazole-3-carbonyl]-hexyl}carbamate 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: 66.0%

: 1605314-24-6
(R)-7-(tert-butoxycarbonylamino)-3-[(3aS,7aS)-2-oxooctahydro-benzo[d]oxazole-3-carbonyl]heptanoic acid

: 100-51-6,185532-71-2
benzyl alcohol

: 1605314-26-8
benzyl {(R)-6-tert-butoxycarbonylamino-2-[(3aS,7aS)-2-oxooctahydrobenzo[d]oxazole-3-carbonyl]-hexyl}carbamate

Guidance literature:: With diphenyl phosphoryl azide; triethylamine; at 20 ℃; for 3h; Reflux;
DOI:10.1002/ejoc.201301834

Reference yield:

: 6404-29-1
6-(tert-butoxycarbonylamino)hexanoic acid

: 1605314-26-8
benzyl {(R)-6-tert-butoxycarbonylamino-2-[(3aS,7aS)-2-oxooctahydrobenzo[d]oxazole-3-carbonyl]-hexyl}carbamate

Guidance literature:: Multi-step reaction with 5 steps

1.1: triethylamine / tetrahydrofuran / 0.25 h / -15 °C

1.2: 2 h / -15 °C

2.1: lithium chloride / tetrahydrofuran / 18 h / 20 °C

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.25 h / -78 °C

3.2: 5 h / -78 °C

4.1: hydrogen; palladium 10% on activated carbon / ethyl acetate / 24 h / 760.05 Torr

5.1: triethylamine; diphenyl phosphoryl azide / 3 h / 20 °C / Reflux

With diphenyl phosphoryl azide; palladium 10% on activated carbon; hydrogen; triethylamine; lithium chloride; lithium hexamethyldisilazane; In tetrahydrofuran; ethyl acetate; 5.1: |Curtius Rearrangement;
DOI:10.1002/ejoc.201301834

Reference yield:

: C₁₆H₂₉NO₅

: 1605314-26-8
benzyl {(R)-6-tert-butoxycarbonylamino-2-[(3aS,7aS)-2-oxooctahydrobenzo[d]oxazole-3-carbonyl]-hexyl}carbamate

Guidance literature:: Multi-step reaction with 4 steps

1.1: lithium chloride / tetrahydrofuran / 18 h / 20 °C

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.25 h / -78 °C

2.2: 5 h / -78 °C

3.1: hydrogen; palladium 10% on activated carbon / ethyl acetate / 24 h / 760.05 Torr

4.1: triethylamine; diphenyl phosphoryl azide / 3 h / 20 °C / Reflux

With diphenyl phosphoryl azide; palladium 10% on activated carbon; hydrogen; triethylamine; lithium chloride; lithium hexamethyldisilazane; In tetrahydrofuran; ethyl acetate; 4.1: |Curtius Rearrangement;
DOI:10.1002/ejoc.201301834