(4-benzyloxycarbonylamino-2,3-dihydroxy-1-isobutyl-6-methyl-heptyl)-carbamic acid benzyl ester

Base Information

• Chemical Name: (4-benzyloxycarbonylamino-2,3-dihydroxy-1-isobutyl-6-methyl-heptyl)-carbamic acid benzyl ester
• CAS No.: 137649-68-4
• Molecular Formula: C₂₈H₄₀N₂O₆
• Molecular Weight: 500.635

Synonyms:(4-benzyloxycarbonylamino-2,3-dihydroxy-1-isobutyl-6-methyl-heptyl)-carbamic acid benzyl ester

Chemical Property of (4-benzyloxycarbonylamino-2,3-dihydroxy-1-isobutyl-6-methyl-heptyl)-carbamic acid benzyl ester

Chemical Property:

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Technology Process of (4-benzyloxycarbonylamino-2,3-dihydroxy-1-isobutyl-6-methyl-heptyl)-carbamic acid benzyl ester

There total 4 articles about (4-benzyloxycarbonylamino-2,3-dihydroxy-1-isobutyl-6-methyl-heptyl)-carbamic acid 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: 15.0%

N-carbobenzoxy-L-leucinal (70853-26-8,86852-22-4,71413-15-5) → (4-benzyloxycarbonylamino-2,3-dihydroxy-1-isobutyl-6-methyl-heptyl)-carbamic acid benzyl ester (137649-68-4)

Guidance literature:

With vanadium(III) chloride; zinc; In tetrahydrofuran; for 1h; Reflux; Inert atmosphere;

DOI:10.1016/j.bmcl.2009.03.041

Reference yield:

(S)-2-amino-4-methylpentan-1-ol (7533-40-6,14438-11-0) → (4-benzyloxycarbonylamino-2,3-dihydroxy-1-isobutyl-6-methyl-heptyl)-carbamic acid benzyl ester (137649-68-4)

Guidance literature:

Multi-step reaction with 3 steps

1: K₂CO₃ / H₂O

2: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -63 deg C, 20 min, 2) -63 deg C, 20 min

3: 1) 2Cl₃(THF)6>22Cl₆>, 2) 1 M HCl / 1) CH₂Cl₂, 3 h, 2) 12 h

With hydrogenchloride; oxalyl dichloride; 2; potassium carbonate; dimethyl sulfoxide; triethylamine; In water;

DOI:10.1021/jo00027a009

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (4-benzyloxycarbonylamino-2,3-dihydroxy-1-isobutyl-6-methyl-heptyl)-carbamic acid benzyl ester (137649-68-4)

Guidance literature:

Multi-step reaction with 3 steps

1: K₂CO₃ / H₂O

2: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -63 deg C, 20 min, 2) -63 deg C, 20 min

3: 1) 2Cl₃(THF)6>22Cl₆>, 2) 1 M HCl / 1) CH₂Cl₂, 3 h, 2) 12 h

With hydrogenchloride; oxalyl dichloride; 2; potassium carbonate; dimethyl sulfoxide; triethylamine; In water;

DOI:10.1021/jo00027a009

upstream raw materials:

N-carbobenzoxy-L-leucinal

(S)-2-amino-4-methylpentan-1-ol

(S)-(-)-N-(benzyloxycarbonyl)leucinol

benzyl chloroformate

Downstream raw materials:

(4S,5R,4'S,5'R)-4,4'-Diisobutyl-[5,5']bioxazolidinyl-2,2'-dione

benzyl alcohol

(1-{1-[1-(5-{1-[2-(2-benzyloxycarbonylamino-3-phenyl-propionylamino)-3-methyl-butyrylamino]-3-methyl-butyl}-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-methyl-butylcarbamoyl]-2-methyl-propylcarbamoyl}-2-phenyl-ethyl)-carbamic acid benzyl ester

(1-{1-[1-(5-{1-[2-(2-benzyloxycarbonylamino-4-methyl-pentanoylamino)-3-methyl-butyrylamino]-3-methyl-butyl}-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-methyl-butylcarbamoyl]-2-methyl-propylcarbamoyl}-3-methyl-butyl)-carbamic acid benzyl ester

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