(2R,3R,4R,5S,6S)-N-[(tert-butyloxy)carbonyl]-3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]-5,6-dihydroxyazepane

Base Information

Chemical Name:(2R,3R,4R,5S,6S)-N-[(tert-butyloxy)carbonyl]-3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]-5,6-dihydroxyazepane
CAS No.:943135-47-5
Molecular Formula:C₃₅H₃₉NO₅
Molecular Weight:553.698
Hs Code.:

Synonyms:(2R,3R,4R,5S,6S)-N-[(tert-butyloxy)carbonyl]-3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]-5,6-dihydroxyazepane

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Chemical Property of (2R,3R,4R,5S,6S)-N-[(tert-butyloxy)carbonyl]-3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]-5,6-dihydroxyazepane

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Technology Process of (2R,3R,4R,5S,6S)-N-[(tert-butyloxy)carbonyl]-3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]-5,6-dihydroxyazepane

There total 9 articles about (2R,3R,4R,5S,6S)-N-[(tert-butyloxy)carbonyl]-3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]-5,6-dihydroxyazepane 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: 87.0%

: (2R,3R,4S,5S,6S)-N-[(tert-butyloxy)carbonyl]-3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]-(5,6-b)-isopropylideneazepane

: 100-39-0
benzyl bromide

: 943135-47-5
(2R,3R,4R,5S,6S)-N-[(tert-butyloxy)carbonyl]-3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]-5,6-dihydroxyazepane

Guidance literature:: (2R,3R,4S,5S,6S)-N-[(tert-butyloxy)carbonyl]-3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]-(5,6-b)-isopropylideneazepane; With triethylsilane; trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2h;

benzyl bromide; With potassium carbonate; In water; ethyl acetate; at 90 ℃; for 18h;
DOI:10.1021/ol502926f

Reference yield:

: 724705-50-4
(2R,3R,4R,5S,6S)-N-benzyloxycarbonyl-2-benzyloxymethyl-3,4-dibenzyloxy-5,6-dihydroxy-azepane

: 943135-47-5
(2R,3R,4R,5S,6S)-N-[(tert-butyloxy)carbonyl]-3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]-5,6-dihydroxyazepane

Guidance literature:: Multi-step reaction with 2 steps

1: triethylamine; H₂ / Lindlar's catalyst / ethanol / 4 h

2: 183 mg / potassium carbonate / ethanol; H₂O / 2 h / Heating

With hydrogen; potassium carbonate; triethylamine; Lindlar's catalyst; In ethanol; water;
DOI:10.1055/s-2007-973884

Reference yield:

: 724705-45-7
(3R,4R,5R)-5-allylamino-3,4,6-tribenzyloxy-hex-1-ene

: 943135-47-5
(2R,3R,4R,5S,6S)-N-[(tert-butyloxy)carbonyl]-3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]-5,6-dihydroxyazepane

Guidance literature:: Multi-step reaction with 5 steps

1.1: aminosulfonic acid / dichloromethane / 2 h

1.2: 2 h

2.1: Grubbs catalyst first generation / 1,2-dichloro-ethane / 16 h / 90 °C / Inert atmosphere

2.2: 16 h / 90 °C

3.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / acetone; water; tert-butyl alcohol / 12 h / 20 °C

4.1: dichloromethane / 12 h / 20 °C

5.1: trifluoroacetic acid; triethylsilane / dichloromethane / 2 h / 20 °C

5.2: 18 h / 90 °C

With Grubbs catalyst first generation; triethylsilane; osmium(VIII) oxide; aminosulfonic acid; 4-methylmorpholine N-oxide; trifluoroacetic acid; In dichloromethane; water; 1,2-dichloro-ethane; acetone; tert-butyl alcohol;
DOI:10.1021/ol502926f