(2S,3R)-2-amino-4-benzyloxy-N-(tert-butoxycarbonyl)-3-hydroxybutyric acid

Base Information

• Chemical Name: (2S,3R)-2-amino-4-benzyloxy-N-(tert-butoxycarbonyl)-3-hydroxybutyric acid
• CAS No.: 174713-20-3
• Molecular Formula: C₁₆H₂₃NO₆
• Molecular Weight: 325.362

Synonyms:(2S,3R)-2-amino-4-benzyloxy-N-(tert-butoxycarbonyl)-3-hydroxybutyric acid

Chemical Property of (2S,3R)-2-amino-4-benzyloxy-N-(tert-butoxycarbonyl)-3-hydroxybutyric acid

Chemical Property:

Purity/Quality:

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Technology Process of (2S,3R)-2-amino-4-benzyloxy-N-(tert-butoxycarbonyl)-3-hydroxybutyric acid

There total 6 articles about (2S,3R)-2-amino-4-benzyloxy-N-(tert-butoxycarbonyl)-3-hydroxybutyric 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: 99.0%

di-tert-butyl dicarbonate (24424-99-5) + (2S,3R)-2-amino-4-(benzyloxy)-3-hydroxybutanoic acid (21768-33-2) → (2S,3R)-2-amino-4-benzyloxy-N-(tert-butoxycarbonyl)-3-hydroxybutyric acid (174713-20-3)

Guidance literature:

With triethylamine; In 1,4-dioxane; water; at 23 ℃; for 10h;

DOI:10.1016/S0968-0896(96)00236-2

Reference yield: 99.0%

(2S,3R)-4-Benzyloxy-2-tert-butoxycarbonylamino-3-hydroxy-butyric acid ethyl ester → (2S,3R)-2-amino-4-benzyloxy-N-(tert-butoxycarbonyl)-3-hydroxybutyric acid (174713-20-3)

Guidance literature:

With lithium hydroxide; In methanol; water; at 4 ℃;

DOI:10.1016/S0040-4039(96)02121-1

Reference yield: 90.0%

N-(tert-butyloxycarbonyl) azide (1070-19-5) + (2S,3R)-2-amino-4-(benzyloxy)-3-hydroxybutanoic acid (21768-33-2) → (2S,3R)-2-amino-4-benzyloxy-N-(tert-butoxycarbonyl)-3-hydroxybutyric acid (174713-20-3)

Guidance literature:

upstream raw materials:

N-(tert-butyloxycarbonyl) azide

(2S,3R)-2-amino-4-(benzyloxy)-3-hydroxybutanoic acid

di-tert-butyl dicarbonate

ethyl 2E-4-(benzyloxy)-2-butenoate

Downstream raw materials:

(2S,3R)-2-((2S,3R)-4-Benzyloxy-2-tert-butoxycarbonylamino-3-hydroxy-butyrylamino)-3-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-butyric acid ethyl ester

{(1S,2R)-3-Benzyloxy-2-hydroxy-1-[((3aS,5S,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethyl)-carbamoyl]-propyl}-carbamic acid tert-butyl ester

Acetic acid (2S,3R,4R,5R,6S)-3,5-diacetoxy-2-[2-((2S,3R)-4-benzyloxy-2-tert-butoxycarbonylamino-3-hydroxy-butyrylamino)-ethyl]-6-methyl-tetrahydro-pyran-4-yl ester

{(1S,2R)-3-Benzyloxy-2-hydroxy-1-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethylcarbamoyl]-propyl}-carbamic acid tert-butyl ester

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