(2R,3R,4R)-2,3-Bis-benzyloxy-4-(tert-butoxycarbonyl-methyl-amino)-5-methoxy-pentanoic acid

Base Information

• Chemical Name: (2R,3R,4R)-2,3-Bis-benzyloxy-4-(tert-butoxycarbonyl-methyl-amino)-5-methoxy-pentanoic acid
• CAS No.: 144681-95-8
• Molecular Formula: C₂₆H₃₅NO₇
• Molecular Weight: 473.566

Synonyms:(2R,3R,4R)-2,3-Bis-benzyloxy-4-(tert-butoxycarbonyl-methyl-amino)-5-methoxy-pentanoic acid

Chemical Property of (2R,3R,4R)-2,3-Bis-benzyloxy-4-(tert-butoxycarbonyl-methyl-amino)-5-methoxy-pentanoic acid

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Technology Process of (2R,3R,4R)-2,3-Bis-benzyloxy-4-(tert-butoxycarbonyl-methyl-amino)-5-methoxy-pentanoic acid

There total 2 articles about (2R,3R,4R)-2,3-Bis-benzyloxy-4-(tert-butoxycarbonyl-methyl-amino)-5-methoxy-pentanoic acid 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:

((1R,2R,3R)-2,3-Bis-benzyloxy-1-methoxymethyl-4-oxo-butyl)-methyl-carbamic acid tert-butyl ester → (2R,3R,4R)-2,3-Bis-benzyloxy-4-(tert-butoxycarbonyl-methyl-amino)-5-methoxy-pentanoic acid (144681-95-8)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; dihydrogen peroxide; In water; acetonitrile; Yield given;

DOI:10.1039/c39920001240

Reference yield:

((1R,2R,3S)-2,3-Bis-benzyloxy-1-methoxymethyl-pent-4-enyl)-methyl-carbamic acid tert-butyl ester (144681-85-6) → (2R,3R,4R)-2,3-Bis-benzyloxy-4-(tert-butoxycarbonyl-methyl-amino)-5-methoxy-pentanoic acid (144681-95-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂

2: NaClO₂, H₂O₂, NaH₂PO₄ / H₂O; acetonitrile

With sodium chlorite; sodium dihydrogenphosphate; dimethylsulfide; dihydrogen peroxide; ozone; In water; acetonitrile;

DOI:10.1039/c39920001240

Reference yield: 78.0%

methyl 2-(4-amino-(2R)-butyl)-4-oxazolecarboxylate (144681-92-5) + (2R,3R,4R)-2,3-Bis-benzyloxy-4-(tert-butoxycarbonyl-methyl-amino)-5-methoxy-pentanoic acid (144681-95-8) → 2-{(R)-3-[(2R,3R,4R)-2,3-Bis-benzyloxy-4-(tert-butoxycarbonyl-methyl-amino)-5-methoxy-pentanoylamino]-1-methyl-propyl}-oxazole-4-carboxylic acid methyl ester (144681-93-6)

Guidance literature:

With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 0 - 25 ℃;

DOI:10.1039/c39920001240

upstream raw materials:

((1R,2R,3S)-2,3-Bis-benzyloxy-1-methoxymethyl-pent-4-enyl)-methyl-carbamic acid tert-butyl ester

Downstream raw materials:

2-{(R)-3-[(2R,3R,4R)-2,3-Bis-benzyloxy-4-(tert-butoxycarbonyl-methyl-amino)-5-methoxy-pentanoylamino]-1-methyl-propyl}-oxazole-4-carboxylic acid methyl ester

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