(5R,7S)-ethyl 7-(benzyloxy)-5-(benzyloxycarbonylamino)decanoate

Base Information

Chemical Name:(5R,7S)-ethyl 7-(benzyloxy)-5-(benzyloxycarbonylamino)decanoate
CAS No.:1446447-15-9
Molecular Formula:C₂₇H₃₇NO₅
Molecular Weight:455.594
Hs Code.:

Synonyms:(5R,7S)-ethyl 7-(benzyloxy)-5-(benzyloxycarbonylamino)decanoate

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Chemical Property of (5R,7S)-ethyl 7-(benzyloxy)-5-(benzyloxycarbonylamino)decanoate

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Technology Process of (5R,7S)-ethyl 7-(benzyloxy)-5-(benzyloxycarbonylamino)decanoate

There total 14 articles about (5R,7S)-ethyl 7-(benzyloxy)-5-(benzyloxycarbonylamino)decanoate 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: 92.0%

: 1446447-14-8
(5R,7S,E)-ethyl 7-(benzyloxy)-5-(benzyloxycarbonylamino)dec-2-enoate

: 1446447-15-9
(5R,7S)-ethyl 7-(benzyloxy)-5-(benzyloxycarbonylamino)decanoate

Guidance literature:: With sodium tetrahydroborate; nickel(II) chloride hexahydrate; hydrogen; In methanol; at 0 - 20 ℃; for 1h;
DOI:10.1016/j.tetasy.2013.05.004

Reference yield:

: 1388220-70-9
(S)-((hept-1-en-4-yloxy)methyl)benzene

: 1446447-15-9
(5R,7S)-ethyl 7-(benzyloxy)-5-(benzyloxycarbonylamino)decanoate

Guidance literature:: Multi-step reaction with 13 steps

1: water; osmium(VIII) oxide; 2,6-dimethylpyridine; sodium periodate / 1,4-dioxane; toluene / 4.5 h / 0 - 20 °C / Inert atmosphere

2: dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere

3: diisobutylaluminium hydride / dichloromethane; hexane / 2 h / 0 °C / Inert atmosphere

4: titanium(IV) isopropylate; D-(-)-diisopropyl tartrate; p-cumenyl hydroperoxide / dichloromethane / 12 h / -20 °C / Inert atmosphere; Molecular sieve

5: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 5 h / 0 °C / Inert atmosphere

6: triethylamine / dichloromethane / 6 h / 0 - 20 °C / Inert atmosphere

7: triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

8: sodium azide / N,N-dimethyl-formamide / 55 °C / Inert atmosphere

9: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

10: water; ethyl acetate / 5 h / 0 - 20 °C / Inert atmosphere

11: 2-iodoxybenzoic acid / dichloromethane; 1,2-dichloro-ethane / 8 h / 0 - 20 °C / Inert atmosphere

12: dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere

13: nickel(II) chloride hexahydrate; hydrogen; sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; sodium azide; nickel(II) chloride hexahydrate; p-cumenyl hydroperoxide; 2-iodoxybenzoic acid; water; hydrogen; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; 2: |Wittig Olefination / 4: |Sharpless Asymmetric Epoxidation / 12: |Wittig Olefination;
DOI:10.1016/j.tetasy.2013.05.004

Reference yield:

: 1446447-07-9
(S,E)-ethyl 5-(benzyloxy)oct-2-enoate

: 1446447-15-9
(5R,7S)-ethyl 7-(benzyloxy)-5-(benzyloxycarbonylamino)decanoate

Guidance literature:: Multi-step reaction with 11 steps

1: diisobutylaluminium hydride / dichloromethane; hexane / 2 h / 0 °C / Inert atmosphere

2: titanium(IV) isopropylate; D-(-)-diisopropyl tartrate; p-cumenyl hydroperoxide / dichloromethane / 12 h / -20 °C / Inert atmosphere; Molecular sieve

3: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 5 h / 0 °C / Inert atmosphere

4: triethylamine / dichloromethane / 6 h / 0 - 20 °C / Inert atmosphere

5: triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

6: sodium azide / N,N-dimethyl-formamide / 55 °C / Inert atmosphere

7: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

8: water; ethyl acetate / 5 h / 0 - 20 °C / Inert atmosphere

9: 2-iodoxybenzoic acid / dichloromethane; 1,2-dichloro-ethane / 8 h / 0 - 20 °C / Inert atmosphere

10: dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere

11: nickel(II) chloride hexahydrate; hydrogen; sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C

With titanium(IV) isopropylate; sodium tetrahydroborate; lithium aluminium tetrahydride; sodium azide; nickel(II) chloride hexahydrate; p-cumenyl hydroperoxide; 2-iodoxybenzoic acid; hydrogen; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; 2: |Sharpless Asymmetric Epoxidation / 10: |Wittig Olefination;
DOI:10.1016/j.tetasy.2013.05.004