(S)-2-Amino-N-tetradecyl-4-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butyramide

Base Information

• Chemical Name: (S)-2-Amino-N-tetradecyl-4-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butyramide
• CAS No.: 145286-59-5
• Molecular Formula: C₅₂H₇₂N₂O₆
• Molecular Weight: 821.153
• Mol file: 145286-59-5.mol

Synonyms:(S)-2-Amino-N-tetradecyl-4-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butyramide

Chemical Property of (S)-2-Amino-N-tetradecyl-4-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butyramide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-Amino-N-tetradecyl-4-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butyramide

There total 8 articles about (S)-2-Amino-N-tetradecyl-4-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butyramide 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:

(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)methanal (140397-46-2) → (S)-2-Amino-N-tetradecyl-4-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butyramide (145286-59-5)

Guidance literature:

Multi-step reaction with 7 steps

1: tetrahydrofuran

2: TsNHNH₂, NaOAc / 1,2-dimethoxy-ethane; H₂O

3: Et₃N, DMAP

4: CsCO₃ / methanol

5: Jones reagent

6: EDC, HOBt

7: TFA

With dmap; jones reagent; sodium acetate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; toluene-4-sulfonic acid hydrazide; trifluoroacetic acid; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; water;

DOI:10.1021/ja00052a072

Reference yield:

(S)-2-Oxo-4-[2-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-oxazolidine-3-carboxylic acid tert-butyl ester (144542-47-2) → (S)-2-Amino-N-tetradecyl-4-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butyramide (145286-59-5)

Guidance literature:

Multi-step reaction with 4 steps

1: CsCO₃ / methanol

2: Jones reagent

3: EDC, HOBt

4: TFA

With jones reagent; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; In methanol;

DOI:10.1021/ja00052a072

Reference yield:

(S)-4-[2-((2S,3S,4R,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-oxazolidin-2-one (144542-39-2) → (S)-2-Amino-N-tetradecyl-4-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butyramide (145286-59-5)

Guidance literature:

Multi-step reaction with 5 steps

1: Et₃N, DMAP

2: CsCO₃ / methanol

3: Jones reagent

4: EDC, HOBt

5: TFA

With dmap; jones reagent; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; trifluoroacetic acid; In methanol;

DOI:10.1021/ja00052a072

upstream raw materials:

[(S)-1-Tetradecylcarbamoyl-3-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propyl]-carbamic acid tert-butyl ester

tetradecylamine

(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)methanal

(S)-4-[2-((2S,3S,4R,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-oxazolidin-2-one