(2S,3R)-(E)-N^α-(tert-Butoxycarbonyl)-N-methoxy-N-methyl-2-amino-6-(benzyloxy)-3-hydroxy-4-hexenamide

Base Information

• Chemical Name: (2S,3R)-(E)-N^α-(tert-Butoxycarbonyl)-N-methoxy-N-methyl-2-amino-6-(benzyloxy)-3-hydroxy-4-hexenamide
• CAS No.: 163625-40-9
• Molecular Formula: C₂₀H₃₀N₂O₆
• Molecular Weight: 394.468

Synonyms:(2S,3R)-(E)-N^α-(tert-Butoxycarbonyl)-N-methoxy-N-methyl-2-amino-6-(benzyloxy)-3-hydroxy-4-hexenamide

Chemical Property of (2S,3R)-(E)-N^α-(tert-Butoxycarbonyl)-N-methoxy-N-methyl-2-amino-6-(benzyloxy)-3-hydroxy-4-hexenamide

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Technology Process of (2S,3R)-(E)-N^α-(tert-Butoxycarbonyl)-N-methoxy-N-methyl-2-amino-6-(benzyloxy)-3-hydroxy-4-hexenamide

There total 2 articles about (2S,3R)-(E)-N^α-(tert-Butoxycarbonyl)-N-methoxy-N-methyl-2-amino-6-(benzyloxy)-3-hydroxy-4-hexenamide 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:

trans-5-<(E)-3-(Benzyloxy)-1-propenyl>-2-oxazoline-4-(N-methoxy-N-methylcarboxamide) → (2S,3R)-(E)-Nα-(tert-Butoxycarbonyl)-N-methoxy-N-methyl-2-amino-6-(benzyloxy)-3-hydroxy-4-hexenamide (163625-40-9)

Guidance literature:

Multi-step reaction with 2 steps

1: conc. HCl / methanol / 3 h / 50 °C

2: Et₃N / CH₂Cl₂ / 1.) 0 deg C, 30 min, 2.) r.t., overnight

With hydrogenchloride; triethylamine; In methanol; dichloromethane;

DOI:10.1021/jo00111a034

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + (E)-(2S,3R)-2-Amino-6-benzyloxy-3-hydroxy-hex-4-enoic acid methoxy-methyl-amide (1026840-32-3) → (2S,3R)-(E)-Nα-(tert-Butoxycarbonyl)-N-methoxy-N-methyl-2-amino-6-(benzyloxy)-3-hydroxy-4-hexenamide (163625-40-9)

Guidance literature:

With triethylamine; In dichloromethane; Yield given; 1.) 0 deg C, 30 min, 2.) r.t., overnight;

DOI:10.1021/jo00111a034

Reference yield: 79.0%

2,2-dimethoxy-propane (77-76-9) + (2S,3R)-(E)-Nα-(tert-Butoxycarbonyl)-N-methoxy-N-methyl-2-amino-6-(benzyloxy)-3-hydroxy-4-hexenamide (163625-40-9) → (4S,5R)-5-<(E)-3-(Benzyloxy)-1-propenyl>-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-(N-methoxy-N-methylcarbamoyl)oxazolidine (163625-45-4)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; Heating;

DOI:10.1021/jo00111a034

upstream raw materials:

di-tert-butyl dicarbonate

(E)-(2S,3R)-2-Amino-6-benzyloxy-3-hydroxy-hex-4-enoic acid methoxy-methyl-amide

Downstream raw materials:

(4S,5R)-5-<(E)-3-(Benzyloxy)-1-propenyl>-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-(N-methoxy-N-methylcarbamoyl)oxazolidine

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