(4R,5S,6S)-6-(benzyloxy)-5-(tert-butoxycarbonylamino)octa-1,7-dien-4-yl acetate

Base Information

Chemical Name:(4R,5S,6S)-6-(benzyloxy)-5-(tert-butoxycarbonylamino)octa-1,7-dien-4-yl acetate
CAS No.:1277172-64-1
Molecular Formula:C₂₂H₃₁NO₅
Molecular Weight:389.492
Hs Code.:

Synonyms:(4R,5S,6S)-6-(benzyloxy)-5-(tert-butoxycarbonylamino)octa-1,7-dien-4-yl acetate

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Chemical Property of (4R,5S,6S)-6-(benzyloxy)-5-(tert-butoxycarbonylamino)octa-1,7-dien-4-yl acetate

Chemical Property:

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Technology Process of (4R,5S,6S)-6-(benzyloxy)-5-(tert-butoxycarbonylamino)octa-1,7-dien-4-yl acetate

There total 10 articles about (4R,5S,6S)-6-(benzyloxy)-5-(tert-butoxycarbonylamino)octa-1,7-dien-4-yl acetate 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:

: 1277172-59-4
(2R,3S)-3-(benzyloxy)-1-(trityloxy)pent-4-en-2-yl methanesulfonate

: 1277172-64-1
(4R,5S,6S)-6-(benzyloxy)-5-(tert-butoxycarbonylamino)octa-1,7-dien-4-yl acetate

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium azide / N,N-dimethyl-formamide / 6 h / 120 °C

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / 0 - 20 °C

3.1: sodium hydrogencarbonate / ethyl acetate / 4 h / 0 °C

4.1: perchloric acid / methanol / 4 h / 20 °C

5.1: pyridine; chromium(VI) oxide; acetic anhydride / dichloromethane / 0.33 h / 0 °C

6.1: iodine; magnesium / tetrahydrofuran / 0.25 h / 0 - 20 °C

6.2: 2 h / -78 °C

6.3: 0 - 20 °C

With pyridine; chromium(VI) oxide; lithium aluminium tetrahydride; sodium azide; perchloric acid; iodine; acetic anhydride; sodium hydrogencarbonate; magnesium; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 6.1: Grignard reaction / 6.2: Grignard reaction;
DOI:10.1002/ejoc.201001171

Reference yield:

: 1042338-99-7
(1S,2S)-(2-benzyloxy-1-hydroxymethyl-but-3-enyl)-carbamic acid tert-butyl ester

: 1277172-64-1
(4R,5S,6S)-6-(benzyloxy)-5-(tert-butoxycarbonylamino)octa-1,7-dien-4-yl acetate

Guidance literature:: Multi-step reaction with 2 steps

1.1: pyridine; chromium(VI) oxide; acetic anhydride / dichloromethane / 0.33 h / 0 °C

2.1: iodine; magnesium / tetrahydrofuran / 0.25 h / 0 - 20 °C

2.2: 2 h / -78 °C

2.3: 0 - 20 °C

With pyridine; chromium(VI) oxide; iodine; acetic anhydride; magnesium; In tetrahydrofuran; dichloromethane; 2.1: Grignard reaction / 2.2: Grignard reaction;
DOI:10.1002/ejoc.201001171

Reference yield:

: C₃₁H₃₁NO₂

: 1277172-64-1
(4R,5S,6S)-6-(benzyloxy)-5-(tert-butoxycarbonylamino)octa-1,7-dien-4-yl acetate

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hydrogencarbonate / ethyl acetate / 4 h / 0 °C

2.1: perchloric acid / methanol / 4 h / 20 °C

3.1: pyridine; chromium(VI) oxide; acetic anhydride / dichloromethane / 0.33 h / 0 °C

4.1: iodine; magnesium / tetrahydrofuran / 0.25 h / 0 - 20 °C

4.2: 2 h / -78 °C

4.3: 0 - 20 °C

With pyridine; chromium(VI) oxide; perchloric acid; iodine; acetic anhydride; sodium hydrogencarbonate; magnesium; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; 4.1: Grignard reaction / 4.2: Grignard reaction;
DOI:10.1002/ejoc.201001171