(R)-benzyl 7-(tert-butoxycarbonylamino)-3-[(3aS,7aS)-2-oxooctahydro-benzo[d]oxazole-3-carbonyl]heptanoate

Base Information

Chemical Name:(R)-benzyl 7-(tert-butoxycarbonylamino)-3-[(3aS,7aS)-2-oxooctahydro-benzo[d]oxazole-3-carbonyl]heptanoate
CAS No.:1605314-22-4
Molecular Formula:C₂₇H₃₈N₂O₇
Molecular Weight:502.608
Hs Code.:

Synonyms:(R)-benzyl 7-(tert-butoxycarbonylamino)-3-[(3aS,7aS)-2-oxooctahydro-benzo[d]oxazole-3-carbonyl]heptanoate

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Chemical Property of (R)-benzyl 7-(tert-butoxycarbonylamino)-3-[(3aS,7aS)-2-oxooctahydro-benzo[d]oxazole-3-carbonyl]heptanoate

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Technology Process of (R)-benzyl 7-(tert-butoxycarbonylamino)-3-[(3aS,7aS)-2-oxooctahydro-benzo[d]oxazole-3-carbonyl]heptanoate

There total 3 articles about (R)-benzyl 7-(tert-butoxycarbonylamino)-3-[(3aS,7aS)-2-oxooctahydro-benzo[d]oxazole-3-carbonyl]heptanoate 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: 53.0%

: 1605314-20-2
tert-butyl 6-oxo-6-[(3aS,7aS)-2-oxohexahydrobenzo[d]oxazol-3(2H)-yl]hexylcarbamate

: 5437-45-6
Benzyl bromoacetate

: 1605314-22-4
(R)-benzyl 7-(tert-butoxycarbonylamino)-3-[(3aS,7aS)-2-oxooctahydro-benzo[d]oxazole-3-carbonyl]heptanoate

Guidance literature:: tert-butyl 6-oxo-6-[(3aS,7aS)-2-oxohexahydrobenzo[d]oxazol-3(2H)-yl]hexylcarbamate; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1.25h;

Benzyl bromoacetate; In tetrahydrofuran; at -78 ℃; for 5h; diastereoselective reaction;
DOI:10.1002/ejoc.201301834

Reference yield:

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

: 1605314-22-4
(R)-benzyl 7-(tert-butoxycarbonylamino)-3-[(3aS,7aS)-2-oxooctahydro-benzo[d]oxazole-3-carbonyl]heptanoate

Guidance literature:: Multi-step reaction with 3 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

With triethylamine; lithium chloride; lithium hexamethyldisilazane; In tetrahydrofuran;
DOI:10.1002/ejoc.201301834

Reference yield:

: C₁₆H₂₉NO₅

: 1605314-22-4
(R)-benzyl 7-(tert-butoxycarbonylamino)-3-[(3aS,7aS)-2-oxooctahydro-benzo[d]oxazole-3-carbonyl]heptanoate

Guidance literature:: Multi-step reaction with 2 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

With lithium chloride; lithium hexamethyldisilazane; In tetrahydrofuran;
DOI:10.1002/ejoc.201301834