benzyl (5R,7S)-7-(benzyloxy)-1-hydroxydecan-5-ylcarbamate

Base Information

Chemical Name:benzyl (5R,7S)-7-(benzyloxy)-1-hydroxydecan-5-ylcarbamate
CAS No.:1446447-16-0
Molecular Formula:C₂₅H₃₅NO₄
Molecular Weight:413.557
Hs Code.:

Synonyms:benzyl (5R,7S)-7-(benzyloxy)-1-hydroxydecan-5-ylcarbamate

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Chemical Property of benzyl (5R,7S)-7-(benzyloxy)-1-hydroxydecan-5-ylcarbamate

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Technology Process of benzyl (5R,7S)-7-(benzyloxy)-1-hydroxydecan-5-ylcarbamate

There total 15 articles about benzyl (5R,7S)-7-(benzyloxy)-1-hydroxydecan-5-ylcarbamate 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: 76.0%

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

: 1446447-16-0
benzyl (5R,7S)-7-(benzyloxy)-1-hydroxydecan-5-ylcarbamate

Guidance literature:: With diisobutylaluminium hydride; In hexane; dichloromethane; at 0 ℃; for 2.25h; Inert atmosphere;
DOI:10.1016/j.tetasy.2013.05.004

Reference yield:

: 85520-72-5
(4S)-hept-1-en-4-ol

: 1446447-16-0
benzyl (5R,7S)-7-(benzyloxy)-1-hydroxydecan-5-ylcarbamate

Guidance literature:: Multi-step reaction with 15 steps

1.1: sodium hydride / mineral oil; tetrahydrofuran / 0 °C / Inert atmosphere

1.2: 4 h / 0 - 20 °C / Inert atmosphere

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

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

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

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

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

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

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

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

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

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

12.1: 2-iodoxybenzoic acid / dichloromethane; 1,2-dichloro-ethane / 8 h / 0 - 20 °C / Inert atmosphere

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

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

15.1: diisobutylaluminium hydride / dichloromethane; hexane / 2.25 h / 0 °C / Inert atmosphere

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; sodium hydride; 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; mineral oil; 3.1: |Wittig Olefination / 5.1: |Sharpless Asymmetric Epoxidation / 13.1: |Wittig Olefination;
DOI:10.1016/j.tetasy.2013.05.004

Reference yield:

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

: 1446447-16-0
benzyl (5R,7S)-7-(benzyloxy)-1-hydroxydecan-5-ylcarbamate

Guidance literature:: Multi-step reaction with 12 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

12: diisobutylaluminium hydride / dichloromethane; hexane / 2.25 h / 0 °C / Inert atmosphere

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