(2S,3S)-N-(benzyloxycarbonyl)-O-(6'-methylheptanoyl)-3-hydroxyleucine benzyl ester

Base Information

• Chemical Name: (2S,3S)-N-(benzyloxycarbonyl)-O-(6'-methylheptanoyl)-3-hydroxyleucine benzyl ester
• CAS No.: 1647153-61-4
• Molecular Formula: C₂₉H₃₉NO₆
• Molecular Weight: 497.632
• Mol file: 1647153-61-4.mol

Synonyms:(2S,3S)-N-(benzyloxycarbonyl)-O-(6'-methylheptanoyl)-3-hydroxyleucine benzyl ester

Chemical Property of (2S,3S)-N-(benzyloxycarbonyl)-O-(6'-methylheptanoyl)-3-hydroxyleucine benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-N-(benzyloxycarbonyl)-O-(6'-methylheptanoyl)-3-hydroxyleucine benzyl ester

There total 12 articles about (2S,3S)-N-(benzyloxycarbonyl)-O-(6'-methylheptanoyl)-3-hydroxyleucine benzyl ester 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: 94.0%

isooctanoic acid (929-10-2) + (2S,3S)-N-(benzyloxycarbonyl)-3-hydroxyleucine benzyl ester (84500-43-6) → (2S,3S)-N-(benzyloxycarbonyl)-O-(6'-methylheptanoyl)-3-hydroxyleucine benzyl ester (1647153-61-4)

Guidance literature:

With dmap; diisopropyl-carbodiimide; In tetrahydrofuran; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.3762/bjoc.10.113

Reference yield:

(2R,3S)-2-(benzyloxycarbonylamino)-1-O-(tert-butyldimethylsilyl)-4-methylpentane-1,3-diol (1647153-54-5) → (2S,3S)-N-(benzyloxycarbonyl)-O-(6'-methylheptanoyl)-3-hydroxyleucine benzyl ester (1647153-61-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 10-camphorsufonic acid; magnesium sulfate / 27 h / 50 °C / Inert atmosphere

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 19 h / 20 °C

3: ruthenium trichloride; sodium periodate / water; tetrachloromethane; acetonitrile / 5 h / 0 °C

4: caesium carbonate / N,N-dimethyl-formamide / 18 h / 20 °C

5: trifluoroacetic acid / chloroform / 24 h / 20 °C

6: dmap; diisopropyl-carbodiimide / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere

With dmap; ruthenium trichloride; sodium periodate; 10-camphorsufonic acid; tetrabutyl ammonium fluoride; magnesium sulfate; caesium carbonate; trifluoroacetic acid; diisopropyl-carbodiimide; In tetrahydrofuran; tetrachloromethane; chloroform; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.3762/bjoc.10.113

Reference yield:

benzyl (4S,5S)-N-(benzyloxycarbonyl)-5-isopropyl-2,2-dimethyloxazolidine-4-carboxylate (1647153-59-0) → (2S,3S)-N-(benzyloxycarbonyl)-O-(6'-methylheptanoyl)-3-hydroxyleucine benzyl ester (1647153-61-4)

Guidance literature:

Multi-step reaction with 2 steps

1: trifluoroacetic acid / chloroform / 24 h / 20 °C

2: dmap; diisopropyl-carbodiimide / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere

With dmap; trifluoroacetic acid; diisopropyl-carbodiimide; In tetrahydrofuran; chloroform;

DOI:10.3762/bjoc.10.113

upstream raw materials:

(2R,3S)-2-(benzyloxycarbonylamino)-1-O-(tert-butyldimethylsilyl)-4-methylpentane-1,3-diol

(4R,5S)-N-(benzyloxycarbonyl)-4-(tert-butyldimethylsilyloxymethyl)-5-isopropyl-2,2-dimethyloxazolidine

(4R,5S)-N-(benzyloxycarbonyl)-4-(hydroxymethyl)-5-isopropyl-2,2-dimethyloxazolidine

(4S,5S)-N-(benzyloxycarbonyl)-5-isopropyl-2,2-dimethyloxazolidine-4-carboxylic acid

Refernces