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

Base Information

Chemical Name:(2R,3R,4R,5S,6S)-N-benzyloxycarbonyl-2-benzyloxymethyl-3,4-dibenzyloxy-5,6-dihydroxy-azepane
CAS No.:724705-50-4
Molecular Formula:C₃₆H₃₉NO₇
Molecular Weight:597.708
Hs Code.:

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

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Chemical Property of (2R,3R,4R,5S,6S)-N-benzyloxycarbonyl-2-benzyloxymethyl-3,4-dibenzyloxy-5,6-dihydroxy-azepane

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Technology Process of (2R,3R,4R,5S,6S)-N-benzyloxycarbonyl-2-benzyloxymethyl-3,4-dibenzyloxy-5,6-dihydroxy-azepane

There total 5 articles about (2R,3R,4R,5S,6S)-N-benzyloxycarbonyl-2-benzyloxymethyl-3,4-dibenzyloxy-5,6-dihydroxy-azepane 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: 68.0%

: 724705-48-0
(2R,3R,4R)-benzyl 3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]-2,3,4,7-tetrahydro-1H-azepine-1-carboxylate

: 724705-49-1
(2R,3R,4R,5R,6R)-N-benzyloxycarbonyl-2-benzyloxymethyl-3,4-dibenzyloxy-5,6-dihydroxy-azepane

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

Guidance literature:: With osmium(VIII) oxide; N-methyl-2-indolinone; In acetone; tert-butyl alcohol; at 30 ℃; for 24h;
DOI:10.1039/b402542c

Reference yield:

: 366815-69-2
(3S,4R)-1,3,4-Tris-benzyloxy-hept-6-en-2-one

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

Guidance literature:: Multi-step reaction with 4 steps

1: 35 percent / NaBH(OAc)3; AcOH / CH₂Cl₂ / 36 h / 40 °C

2: 91 percent / aq. KHCO₃ / ethyl acetate / 6 h / 20 °C

3: 91 percent / Grubbs' catalyst / CH₂Cl₂ / 76 h / 45 °C

4: 68 percent / aq. OsO₄; NMO / acetone; 2-methyl-propan-2-ol / 24 h / 30 °C

With osmium(VIII) oxide; N-methyl-2-indolinone; sodium tris(acetoxy)borohydride; potassium hydrogencarbonate; acetic acid; Grubbs catalyst first generation; In dichloromethane; ethyl acetate; acetone; tert-butyl alcohol;
DOI:10.1039/b402542c

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

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

Guidance literature:: Multi-step reaction with 3 steps

1: 91 percent / aq. KHCO₃ / ethyl acetate / 6 h / 20 °C

2: 91 percent / Grubbs' catalyst / CH₂Cl₂ / 76 h / 45 °C

3: 68 percent / aq. OsO₄; NMO / acetone; 2-methyl-propan-2-ol / 24 h / 30 °C

With osmium(VIII) oxide; N-methyl-2-indolinone; potassium hydrogencarbonate; Grubbs catalyst first generation; In dichloromethane; ethyl acetate; acetone; tert-butyl alcohol;
DOI:10.1039/b402542c